Together, Jill and Josh have decades of experience growing and leading sales organizations to and through hypergrowth and are some of the best leaders in the SaaS space. The sales plays laid out in this book are essential reads for anyone in sales – regardless of role or experience level.”

Mark Roberge, Managing Director at Stage 2 Capital, Professor at Harvard Business School, Former CRO at HubSpot

The operative word in The Modern Sales Playbook is modern and Chapter 10 nails it – write like a human. This book is written by humans who have been around the block and are providing real, tactical advice for how to do it. Straightforward, simple suggestions that you can start incorporating into your business TODAY!  Regardless of the size of your sales team, any one or a mix of these ideas will up their game.”

Bill Binch, Chief Revenue Officer at Pendo


It’s time for sales professionals at all levels, and in all industries, to face some hard truths about our profession:

Today, buyers no longer need to rely on salespeople to find information about a product or service.

They don’t care what their lead score is, or what a team’s sales process looks like, and they definitely don’t want to hear another generic, self-aggrandizing sales pitch.

To put it bluntly, today’s buyers don’t want to be sold to.

So, that’s the end of the book then, right? Buyers no longer want to be sold to, so sales, as we know it, is now obsolete…

Not so fast.

The reality is that as the expectations of buyers evolve, sales development reps (SDRs), business development reps (BDRs), account executives (AEs), sales managers, and sales executives need to evolve alongside them.

As sales professionals, we need to develop a new way of doing things.

A new sales vocabulary.

A new sales playbook.

And that’s exactly why we asked Jill Rowley (Partner at Stage 2 Capital, formerly of Marketo, Oracle, Eloqua, and Salesforce) and Josh Allen (former Drift CRO, formerly of CarGurus and LogMeIn) to write this book.

Between them, Jill and Josh have worked at some of the biggest and fastest-growing SaaS companies in the world. Over the past two decades, they experienced the shifting sales landscape first-hand and have innovated new tactics and strategies for bringing sales into the modern era.

In this book, you’ll find 50 actionable lessons that have helped Jill and Josh excel as sales professionals and lead their teams to and through hypergrowth. Regardless of what stage you are in your career, these 50 plays will help you take your sales game to the next level.

Thanks for reading. We hope you get as much out of Jill and Josh’s lessons as we did.

– The Drift Sales Team 


Building Pipeline

Play #1: Stop Calling Potential Buyers “Prospects”

Jill Rowley By Jill Rowley

I am violently allergic to the word “prospect.” I don’t like it. Instead of “prospects,” I always call them “buyers.” But really, I think of them as future advocates. I think of my buyers as future advocates of the company that I represent, of the product or solution that I sell, and of me, Jill.

Overall, there’s a lot of language we use in sales that is very aggressive and war-like. For example, we separate our salespeople into “hunters” and “farmers.” I always try to look at language through the lens of the customer. I ask myself, “Does this customer want to be hunted or farmed?” (Answer: Of course not!)

The bottom line: We should start to use new language in sales that is more customer-friendly and that reflects the experience today’s buyers actually want.

Play #2: Be Where Your Buyers Are

Jill Rowley By Jill Rowley

Where should salespeople be spending their time? I always say “be where your buyers are.” But to clarify, that doesn’t just apply to social networks. When your buyers are offline and attending events, you should be at those events.

This is something I still do today. Here’s a very real example. I drove from Charleston to Atlanta to go to an event with venture capital investors and entrepreneurs in the startup ecosystem – the people I need to be networking with at this stage in my career. So, I drove 4.5 hours to Atlanta to attend this event. Have I researched and connected with all of these people online? For the people I know are going to be there, most definitely. I’ve looked them up on LinkedIn. I’ve checked to see if they’re on Twitter, Facebook, and / or Instagram. If an event is relevant to my peeps, I want to be there and be prepared.

If your customer is open to you being in her Instagram feed, then you should consider being on Instagram. It’s all about being where your buyers are. It’s all about being visible and valuable to your buyers. It’s all about knowing more, caring more, and doing more for your buyers. Offline, online, ALL THE TIME.

However, we also have to make sure that we’re not too generic. We need to be careful about making blanket statements like, “Everybody has to be on Twitter, or Facebook, or Instagram, or Snapchat, or LinkedIn.” (Although to be fair, I do think that all salespeople need to be on LinkedIn.)

Play #3: Lean Into LinkedIn

Josh Allen By Josh Allen

Building pipeline is really just about getting to know your buyers. It’s about doing research and understanding what’s important to them and what really matters to them.

The more you understand about the person you’re reaching out to, the more likely you are to make a connection because you’re genuinely showing that you have taken the time to understand who they are, a little bit about what they do, and some of what they work on at their company.

You have to have a genuine curiosity and willingness to walk a mile in someone else’s shoes before you can have a smart conversation with them about anything. The tactic is to take the time, do the research, and understand who you’re reaching out to.

For our sales team here at Drift, LinkedIn is the most powerful network for doing that research. You can learn a tremendous amount about an organization, its size, who used to work there, who works there now, and how their roles have changed over time.

People also tend to be more receptive to getting messages on LinkedIn. From a communication standpoint, it’s less crowded than email, which makes it a great option if you’re doing outreach.

Play #4: Dare To Be Different

Josh Allen By Josh Allen

One thing we have really taught our team here at Drift, and have held onto dearly, is the belief that if we are going to do outbound, if we’re going to reach out to somebody, we need to have something to say. It needs to be interesting and attention-grabbing. Our message needs to stand out from everything else a potential buyer is getting.

For us, that can mean creating personalized videos or creating animated GIFs that show what our product will look like once it’s up and running on their website.

Whatever you do, remember that you can’t be perceived as better unless you’re perceived as different. It’s the only way.

Qualifying Leads

Play #5: Give Contextual Customer Examples

Jill Rowley By Jill Rowley

The most important thing SDRs need to be able to do is make a “deposit.” They need to be able to deliver something of value to the buyer before asking for a “withdrawal’ (15 minutes of someone’s time).

Ultimately, many of the activities SDRs are doing aren’t actually creating the conversations buyers want to have. Nobody wants to be marketed to or sold to, so what is the role of the SDR? It’s not to market or sell. It’s to create the opportunity and environment for conversations that are contextual to the buyer – to that human person that is on the other end (and to the buying committee, because it’s not just one buyer anymore). So, it’s the ability to put it all into context.

I remember when I was at Eloqua we had the annual Markie Awards, which culminated in an annual award ceremony. Every year, we awarded and celebrated our best customers for things like Fastest Time to Value, Rookie of the Year, Marketing & Sales BFFs, and Best International Campaign. One year I was on the judging committee, I had the award submissions printed and categorized into folders – 170 of them. I went through each one and highlighted certain things like, “Oh, this company uses Microsoft Dynamics CRM versus Salesforce, or they switched to Eloqua from a competing marketing automation platform.” Then, when I was talking to a potential buyer who was using Microsoft Dynamics CRM, I’d be able to refer back to the Markie Award-winning customer and highlight their success.

☝That overlap in context is compelling, and it helped me create stronger connections with future customers.

At the rep level, it’s important to know which of your customers are generating the most value and what tools and service providers they’re using to accomplish that. Then it’s up to you to share those specific, contextual examples with future customers.

Play #6: Use Chatbots To Streamline Your SDR Strategy

Josh Allen By Josh Allen

It wasn’t that long ago when the role of an SDR or BDR was centered around brute force. Performance was measured by how many phone calls you made.

The biggest difference between SDR strategy today and SDR strategy back then is that today we have an actual strategy. In the early days, it was all based on headcount. If we had three enterprise reps, we’d say, “Alright, let’s hire one SDR and he or she is going to make 100 calls a day.” That was the extent of the strategy.

Today, new technology – chatbots in particular – allow SDRs to hone in on high-quality leads that are coming through a website. Instead of using brute force and hitting the phones as many times as they can and seeing what trickles out the other end, they can do their jobs more intelligently and efficiently.

As a sales leader, I can now say, “Okay, let’s have this SDR engage with the ten best leads that our chatbot has qualified on our website.” That’s a much better use of that SDR’s time than having him or her make hundreds of cold, outbound calls. Chatbots take a lot of static and noise out of the job, making it easier for SDRs to connect with potential customers. As a result, it becomes easier for sales leaders to make predictions like, “If I hire a new SDR, train that SDR for two to four weeks, I know that on average he or she is going to book eight to ten meetings, which are going to be worth X amount.” There’s now a whole formula to building a tight strategy.

Another reason chatbots have become a crucial part of the modern SDR process is that you get a lift on both sides: Since SDRs are able to do a better job qualifying potential customers, AEs are able to dedicate more of their time to live opportunities and breaking into strategic accounts. So you get a more efficient return out of both your SDR group and your AE group.

Play #7: Remove Friction By Removing Forms

Jill Rowley By Jill Rowley

Conversational marketing is catching on faster than any of the marketing and sales movements that came before it. And that’s because marketing technology has been around for a while now. Marketers and SDRs have had ample time to use what’s available, and they’ve recognized that simply doing more of the status quo isn’t working. More content, more calls, more lead capture forms – just doing more isn’t going to work. You need to do better.

I don’t want to fill out a freaking form to read your white paper. So please, take the form away. Get the friction out of the process. Take the friction out and let me do what I want to do, on the channels that I want to be on, in the timeframe that I want to be operating in.

The expectations of buyers are so much higher today than they were just a few years ago. If you’re still stuck using forms instead of optimizing for a great customer experience, your competitors are going to pass you by.

Sales Email

Play #8: Do Your Research Before You Send

Jill Rowley By Jill Rowley

Email is the cockroach of the internet.

Now that every marketer and every salesperson has everybody’s email address and the ability to automate a series, sequence, or cadence of emails to everybody, nobody wants to check their email. All we want to do when we go into our email is delete, delete, delete. We’re looking for the delete button so we can get all the crap out of our inboxes.

I actually pay for two different services that filter my email. Why? Because I just hate email so much. Does that mean it’s a dead channel? Absolutely not. It’s not a dead channel. It still exists. We’re not getting rid of it. Slack will not replace email anytime soon.

So, how can salespeople use email effectively? For me, it comes down to this:

Do not send me an email if I’m not your ideal customer. If you haven’t done the research on me, do not email me. Do not put me on your list and spam me.

The only time it does make sense to email me (or any potential buyer) is when you actually have something worthwhile to say that you know I will find relevant based on your research. Before you hit send, you need to know me. You need to know where I work, you need to know what I do, you need to know what kinds of problems I might be struggling with, and you need to know what types of tools I’m using day in, day out. Otherwise, don’t bother sending me an email.

Play #9: Stop Wasting Time Trying To Write The “Perfect” Email

Josh Allen By Josh Allen 

One of the most common sales email mistakes I notice is that salespeople spend too much time writing them. That, to me, is the biggest one: Everyone tries to be Shakespeare in their email. They try to write the perfect sentence and use the perfect words. I’ve even seen reps on the sales floor give each other high-fives over well-written email sequences.

But here’s the thing: as an executive, the chance that I’m ever going to read an email you write is very, very low. In fact, when I have a spare minute in my day, one of my favorite things to do is to go through my inbox and swipe-left-delete outreach emails that I know I’m not interested in. So there’s a chance that somebody spent a half hour writing an email that I’m never going to see ?‍♂️

Of course, you want to say something smart in your emails, but you’ve also got to be able to time-box it and understand that of the emails you’re sending out, for every ten you send, maybe only three get read, especially if they’re cold. For those three that get read, you need to have something of value in there, but it needs to be short and concise. If the value’s there and the call-to-action makes sense for who’s receiving it, the elegance of your prose doesn’t matter.

Your buyers don’t care if you write like Shakespeare. They care if you can help them solve an actual problem.

Play #10: Cut The Jibber Jabber & Write Like A Human

Jill Rowley By Jill Rowley

A lot of salespeople make the mistake of taking on a formal, stuffy persona when writing emails.

Don’t do that.

Instead, write like you talk. You need to sound like a human in order to make a human connection.

When you go to write your next email, do away with the business-speak and the marketing jibber jabber. Because if an email reads like a generic marketing pitch, guess what? I don’t want it.

I can always tell when I get a new SDR assigned to me because they all follow the same cadence: Call, email, call, email. And if I decide, for example, to attend a webinar that an SDR has been promoting, the follow-up is predictable. I’ll get a barrage of emails that say something like, “You attended our webinar, why haven’t you purchased from us yet? We’ve been calling and emailing you non-stop. Are you trapped under an elephant?”

☝️ That’s not a human interaction. That’s an interruption. That’s bothering people. Add value and write like a human, or get lost.

Sales Conversations

Play #11: Use The Right Channel At The Right Time

Josh Allen By Josh Allen

At Drift, we’ve started to amass data around where we use certain channels for certain outreach. So, for example, instead of doing a video for our first outreach, we’ll often do it for a second or a third touch – after we’ve already engaged someone and established a connection.

It’s not worth it to take ten minutes to create a custom, personalized video and then send it out if the open rate is going to be 5%. But if we know the open rate is going to be 23% (which is the average we see for second touches), then creating and sending that video becomes worth it.

The important thing here is to know what the math is. Figure out what channel is working and when to use it.

At the end of the day, your goal shouldn’t be to make it easier for you to sell, it should be to make it easier for your customers to buy. And in order to do that, you need to use the communication channels your customers want to use. That’s how you keep a conversation going after you’ve had that first interaction.

Play #12: Use Video To Create A Deeper Connection

Jill Rowley By Jill Rowley

You should always take a buyer-centric approach to answering questions. For SDRs and AEs, that means using the channels that buyers prefer to use (just like Josh mentioned in play #11). So, if the buyer says, “Look, if you need to reach me, call me,” then that rep should use the phone. If the buyer says, “Hey, just send me a text,” then that rep should send a text. The overarching principle is that you always need to be in service to your buyers.

That being said, if your buyer doesn’t want to do a video call, I think you should push them on that. You should try to push them into the modern age, which is video.

With video, your buyer gets to see the real you, face-to-face. Outside of an in-person meeting, video allows for the deepest connection possible, which leads to stronger, more meaningful relationships. And developing those relationships between buyer and seller is how you build a successful brand and a successful business.

Play #13: Smoke Out Objections As Early As Possible

Jill Rowley By Jill Rowley

Dealing with objections is a natural part of a salesperson’s job. But instead of dreading them or avoiding them during sales conversations, you should try to smoke them out as early as possible.

One objection I hear frequently from a lot from buyers is, “It’s just not good timing.” Well, why isn’t it good timing? If you dig into that objection and ask questions, you end up learning more about your potential buyers. For example, you might learn that a buyer has three other competing projects they’re working on. And then you can dig into those. You might learn that a buyer is planning to implement X, Y, and Z before implementing A, B, and C. And maybe you can offer guidance around that and start having a conversation around what they’re prioritizing, and why.

Back when I was doing social selling and offering social selling training services, I got a lot of interest from business leaders at IBM. But once the conversation started progressing, I quickly realized I was talking to the wrong people. Because I knew the industry so well and was tapped into everything that was happening, I knew that IBM had a corporate initiative around social selling and that any sale I made would ultimately have to go through them. There were potential objections lurking in my future, so instead of wasting my time, I connected with IBM’s corporate leaders and started having conversations with the actual decision-makers. That way, I could avoid having the deal potentially blow up in my face over objections I hadn’t yet heard.

As a sales rep, you’ve got to smoke those things out.

Play #14: Hone In On A Specific Pain Point

Josh Allen By Josh Allen

If during sales conversations potential buyers keep raising the issue of price, it’s an indication that they don’t understand the value of your product and how using it can make their lives easier. This, in turn, can mean a couple of things:

  1. It can mean you’re talking to the wrong people.
  2. It can mean you’re doing a poor job of positioning your product and showing people how it can solve a specific pain point they have.

Let’s hone in on that second point, and I’ll use conversational marketing as an example.

When I talk about conversational marketing to potential buyers, some of them will inevitably think of it as a buzzword. They won’t see it (at least not right away) as a real pain point for them. And that’s when I start asking questions like…

  • “How much money are you spending to drive traffic to form-fill pages?”
  • “How many meetings are you generating from those form fills?”
  • “Is that enough meetings to drive the pipeline you need to generate?”

It’s so important to steer the conversation away from the features and benefits of what I’m selling to focus on uncovering the problems they’re actually experiencing. That’s how you get the value proposition to bubble to the surface. And it all starts with identifying a specific pain point that buyer is experiencing.

Play #15: Understand What Matters To Every Stakeholder In A Deal

Josh Allen By Josh Allen

Sometimes I’ll see sales reps on a video call and their screen will look like the opening credits of The Brady Bunch: Nine faces staring back at them.

This is a phenomenon you’ll often experience when working on bigger, more complicated deals: More people get involved. And each of those people plays a different role.

As a salesperson, it’s your job to understand the wants and needs of each individual stakeholder and to provide satisfactory answers to all of their questions. Because if you don’t, if you only have eight of the nine people on board with your proposal, that one person can become an obstacle who can slow down (or potentially stop) a deal. Ultimately, there are backroom conversations between stakeholders that you won’t be privy to. That’s why it’s crucial to address every objection up front, regardless of who raises it.

When I was at LogMeIn, I was working on a big deal with a large Canadian-based telecommunications company and there was a lower-level manager I was talking to who I just assumed didn’t have a lot of influence. And, admittedly, I didn’t do a great job of answering that manager’s questions and assuaging his concerns.

As I later found out, that manager was incredibly well-respected within the company and ended up slowing the deal down because he felt the solution I was offering was inferior to what his team was already using. He didn’t think it was worth it to go through the hassle of switching.

The takeaway: You need to appreciate every single individual who’s involved in a deal because there’s a reason they’re a part of it. And you need to understand how your product will affect those individuals specifically.

Product Demos & Presentations

Play #16: Use A Scheduling Tool

Jill Rowley By Jill Rowley

One of the biggest time-wasters in sales: going back and forth with a potential buyer in order to set up a meeting.

When I started in sales, there weren’t any other options. You were forced to play endless games of phone tag and send countless emails, all just to figure out a time for a product demo that fit the schedules of both parties.

Today, intelligent scheduling tools do all the work for you, and they integrate directly with your calendar. That way, potential buyers can see when you’re available and choose times that work best for them.

Just like with removing forms, using a scheduling tool removes friction from the buying process. Specifically, it removes the logistical aspect of nailing down a meeting time. And from a salesperson’s perspective, it helps you stay organized.

This isn’t just a nice-to-have for modern salespeople, it’s a must-have.

Play #17: Check Meeting Invites To See Who’ll Be Attending

Jill Rowley By Jill Rowley 

Sometimes a buying committee will try to hide who else is going to be in a room during a meeting or product demo. That’s not productive for either side, but unfortunately, it still happens.

As a salesperson, you need to know everyone you’re going to be talking to so you can A) bring the right people into the conversation from your side and B) do your research ahead of time and understand the potential pain points someone might raise.

Figuring out who’s going to be in a meeting or product demo can be as simple as looking at the meeting invite on your calendar and checking to see who else has been added. If you’re not doing that, then we have a bigger problem.

Now, if you don’t see any other names on the invite, you should ask a potential buyer up front, “Who else in your organization will be attending?” It may seem inconsequential, but as Josh explained in Play #15, having an understanding of what each individual stakeholder wants is crucial to overcoming objections and getting deals over the finish line.

Play #18: Ditch The Script

Josh Allen By Josh Allen

A product demo or sales presentation is equal parts give and take. Going into it, you need to know: What are the success criteria? How do you know if it makes sense to move onto next steps after you demo or give a presentation? Ultimately, the answers to those questions are going to vary based on the specific things potential buyers are looking for.

Preparing for a demo is really about knowing who your buyer is, knowing who’s in the room, knowing what they care about, and knowing why they’re interested in the first place. And if you present to that, if you demo to that, as opposed to just having a cookie-cutter or boilerplate demo that you go through every time, then you’re going to have a higher likelihood of being able to land that account.

Unfortunately, some sales executives still think about demos and presentations as “reps and sets.” They think that by practicing the same script over and over, regardless of who you’re talking to, you’ll get better at it.

In reality, it’s better to take the time to understand who you’re actually dealing with and to speak to them as individuals. There should never be a single pitch you use every time – it always needs to be different. It always needs to be personalized.

Play #19: Practice CRM Discipline

Josh Allen By Josh Allen

CRM discipline is common among top performers, especially in high-velocity sales environments where you’re doing a lot of transactions. Because when you talk to so many people, send out so many notes, record so many videos, and you do so many different things, it’s really easy to lose track.

If you’re not good about knowing where you left off, that’s a major problem. Luckily, tools like Salesforce give you full control over your ability to stay organized.

One way you can make this easier is to structure Salesforce in a way that makes it like spoon-feeding the questions you want to ask as you’re going through the sales process. Because the reality is that most salespeople are extroverts. They’re great storytellers. They’re happy to be in front of customers. They’re excited by it. And they’re eager to get back to having more conversations as opposed to doing the admin work and recording everything they talked about in previous conversations.

The best salespeople appreciate why that admin work is necessary because they’ve burned themselves in the past and forgot to follow up. I’ve noticed at Drift that our best performers are the ones who can track longer term deals. Sometimes those deals take six or even nine months before they come to fruition. Only by having strong CRM discipline are salespeople able to track those deals and stay with them until they’re closed-won.

Play #20: Make Your Follow-Ups Count

Jill Rowley By Jill Rowley

Follow up is so freaking important.

Why? Because most people today don’t do what they say they’re going to do. And more specifically, they don’t do what they say they’re going to do when they say they’re going to do it.

As a salesperson, you can differentiate yourself by breaking this pattern. That alone will go a long way.

Also, when you do follow up, make sure you actually have something to say, or a question to ask. I don’t ever want to see another email from a salesperson that says, “I’m just circling back,” or “I’m just touching base,” or “I’m just checking in.”

Don’t circle back with me.

Don’t touch base.

Don’t check in.

Make a deposit!

If you’re not going to tell me something new, or give me a nugget of something valuable, don’t bother following up.

Sales Measurement

Play #21: Start With The End In Mind

Josh Allen By Josh Allen 

I am a huge proponent of sales math. It’s something that we rolled out here at Drift, and at its core, it’s about starting with the end in mind. What’s your end goal? What’s your quota? How much do salespeople want to earn? And then you work backward from that to figure out how much you need in the pipeline, i.e. how many opportunities you need to create. And then you work backward from that to figure out how many meetings you need to book in order to create those opportunities. Finally, you work backward from that to figure out how many quality activities you need in order to book those meetings.

Here’s an example: Let’s say you have a $5K quota. Now, you’re not going to hit that all in one day. But you’ve got to start somewhere. So, when you come into work each day, you think to yourself, “I know that doing 30 quality activities a day will get me five meetings. And I know that those five meetings will result in two opportunities. And I know that those two opportunities are worth $2K. And I know I need a rolling monthly pipeline of $20K.”

So, you can figure out how your daily activities will get you to your end goal because you know what your close rate is against your pipeline, and you know what your conversion rate is from meetings to opportunity, and you know what your conversion rate is from quality activities to meetings. By starting with the end in mind, you can make your sales performance more predictable. And the best part is, it puts you in control of your results. It allows you to understand what a good day looks like – so you can leave the office feeling good about your output every single day.

Play #22: Measure Customer Advocacy (A Lagging Indicator)

Jill Rowley By Jill Rowley

When measuring sales performance, there are leading indicators and lagging indicators.

Leading indicators reveal immediate progress and help show how likely you are to hit your future goals. For example, average revenue per customer is a leading indicator of what your overall revenue might end up looking like at the end of the year.

Lagging indicators, on the other hand, are the outputs. They’re the results you see after the fact. And for a lot of sales teams, the most important metric they measure is a lagging indicator: annual revenue.

For me, the most important metric you can measure in sales is a different lagging indicator. It isn’t revenue, it’s customer advocacy.

Customer advocacy refers to the degree to which your customers are not only succeeding with your product but also actively promoting your product to other potential buyers. When your company has strong customer advocacy, your best “salespeople” aren’t on your payroll – they’re your customers themselves.

In order to produce that result, your actual salespeople need to focus on what’s best for their customers. To get people to be advocates of your company, you first need to be great advocates of theirs. That means, as a salesperson, making your customers as successful as possible should be your number one goal while hitting a revenue target should come second.

Play #23: Focus On Individuals (Not Averages)

Josh Allen By Josh Allen

It’s really easy for a sales leader to say, “You need to make 50 dials a day. That’s what the average is on the team. We know that if you do an average of 50 dials, we’ll get the result we want, which is to book five meetings.”

And while setting a benchmark like this can be helpful in some situations, especially to give a new hire guidance out of the gates, it overlooks the fact that different salespeople have different skill sets. For example, some salespeople are great on the phone and might be able to book five meetings with just 20 dials. In contrast, some salespeople struggle on the phone and might need to make 100 dials before they’re able to book five meetings. So, from a measurement perspective, holding everyone to that same 50-dial benchmark doesn’t always make sense.

At Drift, when we hire new salespeople, we start by giving them the averages. Then we weigh their performance out over time and figure out where they settle in. Here’s our thinking behind that: For people on our team, we know what their quota is. And when they’ve been around for a while, we know what their average pipeline has been. We know what their conversion rate has been. We know all these things, so we can go to them and say, “This is how many quality activities we suggest you do. Right now you’re 10% lower than that on a daily basis, so if you boost that by 10%, the rest of it is going to take care of itself.”

The trick is to set those benchmarks at an individual level as opposed to blanketing the team with a directive and saying, “You have to do this every day.” Personalizing it and focusing on the individual is what makes it work.

Play #24: Pay Attention To The Mix Of Deals (Not Just Deal Volume)

Jill Rowley By Jill Rowley

At the end of the day, in sales, the rubber still meets the road with revenue.

Salespeople, after all, have incomes that are largely based on commission. The amount they earn is tied directly to how many dollars they bring in the door. And when you count up those dollars at the end of the month, or at the end of the quarter, it’s always clear who the top salesperson is. And it’s always clear who closed the most deals.

Those metrics are definitely important. But at the same time, I think it’s equally important to look within that and to measure the mix of deals salespeople close.

Are they little ones?

Are they little and big?

Are they proof-of-concept deals or pilots?

Are they all 12-month contracts? Or are they longer?

By digging into the mix of deals, you can better identify the strengths and weaknesses of different reps and help them improve. For example, if Bob is only doing 12-month contracts, while Mary is doing three-year contracts on a consistent basis, it might be worthwhile to have Bob learn from Mary about how he can negotiate those longer contracts.

Play #25: Simplify Your Dashboard

Josh Allen By Josh Allen

There’s a tendency to overcomplicate as opposed to simplifying. Simple is hard because it forces us to be reductive when the natural tendency is to add more stats, more numbers, more graphs, more everything.

But I think the simpler you make your sales dashboard at the management level, and at the individual level, and at every level in-between, the easier it becomes for you to manage the business.

Even with a simplified main dashboard, it’s easy to get nuanced and dive into very specific details when you need to. You can do that with sub-dashboards, or subcategories, or by doing deep-level inspections when something’s not working. But as a sales leader, you can’t afford to look at minutiae every day. It just gets in the way of the actual heartbeat of the organization.

Sales Leadership

Play #26: Keep An Even Keel

Josh Allen By Josh Allen

I think the most important quality a sales leader can have is consistency – or the ability to keep an even keel when faced with the inevitable peaks and valleys of sales.

Because here’s a secret about sales: it’s constant peaks and valleys. If you’re in a monthly business, twelve times a year you’re faced with peaks and valleys. Quarterly, it’s four times a year. So the best sales leaders are able to maintain a steady, objective leadership style in the good times and the bad.

For example, let’s say I’m a sales rep and I’m having a bad month. So I go to my manager and I say, “Here are the things that are going on. This is what I’m finding. This is what I’m seeing.” If the reaction of that sales manager is to blow up in my face and put me down and make me feel terrible about myself, guess what? I’m not going to go to my manager anymore when I’m dealing with a problem.

So the best leaders, during both the peaks and the valleys, are able to react objectively with feedback, with recommended actions, and with teaching, coaching, and guidance versus just having an emotional reaction. And I think that’s super important, especially in sales where there’s a tendency for people to get overly amped up when they’re having a really good month and, then the reverse, to get incredibly low when things aren’t going well. To succeed in sales at any level, you need to find balance.

Play #27: Use Data To Set Realistic Sales Targets

Jill Rowley By Jill Rowley 

Something I learned early in my sales career is that generally as a sales organization grows, your territory gets smaller while your quota gets bigger.

If you think about the natural growth progression of a company as it starts to invest more in marketing and sales, sales will inevitably start to grow alongside that. So, you need more salespeople. But if, as a company, your sales territory stays the same (e.g. you remain US-centric and keep serving the same 50 states), you’re going to need to carve out a little bit for the new recruit, right?

These are the types of nuances you need to consider in order to set realistic sales targets that motivate your team. You can’t simply pull a number out of the air and say, “We want to grow 120% next year.” You have to build up those numbers based on a multitude of factors, including the investments that you’re going to make, the historical conversion rates that you’ve experienced, the number of reps that you have, and the productivity of the team. Only by digging into that data will you be able to dole out sales targets fairly.

Play #28: Balance Your Left Brain & Right Brain

Josh Allen By Josh Allen

Great sales leaders – especially in this day and age – are equal parts left- and right-brained.

It used to be that you could just be an extrovert and a good storyteller and that’s what made you a great salesperson and, with the right grooming, potentially a great sales leader. But today that’s not enough.

In order to succeed as a sales leader, you need to be able to dig into data, to quantify the impact, and to understand the quantitative implications behind the decisions you make. And this is something that really didn’t come about until the mid- to late-2000s when you started seeing high-velocity sales at SaaS businesses.

With the rise of SaaS came the need for sales leaders to be able to demonstrate equal parts extroversion and the ability to use data to make decisions. And that applies at the individual level, too. For example, if you’re selling a product like Drift, you’ve got to be able to go to a potential buyer with a point of view that is data-driven and that is based on their conversion rate, or how many qualified meetings they’re trying to drive to their SDR team, or whatever it is they’re trying to move the needle on.

Regardless of where you are in your sales career, being equal parts left-brained and right-brained will be crucial to your future success. And since most sales professionals have a natural tendency to favor their right brain (i.e. the subjective, intuitive, creative side), you need to make an effort to tap into your left brain (i.e. the objective, analytical, scientific side). That means avoiding knee-jerk reactions to things like territory changes, comp plan changes, and quota moves. And for sales leaders – to hiring and firing. You need to strive for balance and make a conscious effort to be equal parts data-driven and people-driven.

Play #29: Keep An Open Dialogue With Your Team

Josh Allen By Josh Allen

It would be unfair to ask somebody to lead a sales organization through different stages of growth if they hadn’t been through those stages of growth already. Because there is a feeling to it, and more than anything, a leader’s responsibility when going through different stages of growth is to let people know whether or not what they’re feeling is normal.

When you have a leader who’s been through it a couple of times, who’s “seen the movie” before, that leader can – and should – recall stories of the feelings, experiences, changes, and mistakes that people can expect as a company grows. (Although hopefully, that leader will help his or her team avoid making the same mistakes he or she made earlier.) The underlying goal should be to have an open dialogue with the team and, when things go bad, to reassure the team that the world is not ending.

If you look at HubSpot, LogMeIn, CarGurus, Toast, Slack, Airbnb, Uber, Pinterest, whomever… all of those companies experienced peaks and valleys. As a sales leader, it’s one of my core responsibilities to help my team understand what to expect based on the different stages of growth we’re in. It’s my job to talk openly and to answer questions about what’s going on, why a particular stage might be hard, and what we can do about it as a team to turn things around. As a leader, that’s how you create a trust and transparency loop within your team.

Sales Career Development

Play #30: Be Confident & Courageous (But Not Cocky)

Jill Rowley By Jill Rowley

One of the most important lessons you can learn as your sales career develops is that it’s okay to whiff. In order to succeed in this field, you can’t be afraid to swing big. Even if you’re just starting out, you need to be confident and you need to be courageous. Why? Because people don’t want to buy from someone who seems unsure about what they’re talking about. Someone who falters and backtracks adds friction to the buying process, and as a salesperson, it’s your job to do the opposite – you should be removing friction, not creating it.

At the same time, however, you need to remember that there’s a fine line between being confident and being cocky. And I know personally I’ve crossed that line sometimes. While buyers react positively to confidence, they tend to react poorly to cockiness.

One trick I use for remembering where the line is: I think about my daughter’s first time at the driving range. She had never played golf before. She had never swung a club. But she walked up with her big golf bag over her shoulder, she took out a club, and she whiffed. She whiffed repeatedly. But she never stopped trying. Was she cocky? Of course not. She knew she had a lot to learn. But that didn’t stop her from approaching the tee with confidence and giving it all she had. She wasn’t afraid of what the other people at the driving range thought of her. Instead, she stayed laser-focused on getting better.

Play #31: Learn To Ask The Tough Questions Up Front

Josh Allen By Josh Allen

The SDRs who go on to become great AEs are the ones who first excel in the role they’re already in. They dominate that first phase in their career trajectory. And, more specifically, they tend to have a particular characteristic: They aren’t afraid to ask tough questions up front. As a result, they can quickly get to the bottom of whether or not someone is a good fit, and, if someone is a good fit, they can quickly understand that person’s pain points.

This ties into the (false) notion that winning a deal happens at the end of the sales process. In reality, winning a deal happens at the beginning. And the really good SDRs ask questions that open up deals early on.

As a sales leader, you need to keep an eye out for SDRs who exhibit those characteristics and who aren’t afraid to ask the right types of questions to find out if there’s something there.

Play #32: Scale Your Team Through Internal Development

Josh Allen By Josh Allen

I think the only way you scale is if you develop. To me, the two go hand in hand.

Think about it this way: Let’s say our sales organization at Drift, which is about 80 people today, grows to 200 people in the next two years. We won’t be able to get to that 200 by going out and hiring a bunch of enterprise reps and managers from other companies who have no clue how to sell our product. Instead, the best course of action is to develop the people who already have great institutional knowledge, who have demonstrated proficiency in their current roles, and who are ready to take on more responsibility.

As a sales leader, you should create a graduation process within your team where somebody who comes in as an SDR can move up and carry a quota for the SMB (small and medium-sized business) team. And then a great SMB performer can move up to the SME (small and medium enterprise) team. And a great SME performer can move up to enterprise. Finally, someone who does really well on the enterprise team can either take on more responsibility within that team or potentially move into an international role, or a satellite role that opens up as a result of the growth your company’s going through.

My biggest responsibility is to develop my managers to be focused on coaching, teaching, and developing their individuals because they all need to flow through the organization in order for us to scale.

If you don’t invest the time, if you don’t develop the team, you’ll be left spinning your wheels trying to grow. But if you create the structure for internal growth, you create an environment where successful people can level up and tackle new challenges. Which then opens a seat for the next successful person behind them. It’s a virtuous cycle that feeds the talent growth of a company for years.

Play #33: Create A Culture That Celebrates Customer Success

Jill Rowley By Jill Rowley

 When building an SDR team, the traditional approach is to hire a bunch of recent college graduates. Of the more than 4,500 universities and colleges in the United States, less than 4% have any type of sales curriculum or programs. Because there are fewer than 200 colleges and universities that have curriculum for professional selling, the first thing you’ll need to check is: Do these junior employees have the business acumen that they need? Then, the second and, arguably, more important thing you’ll need to check is: Do they have the customer acumen that they need?

The truth is, many sales organizations fail to provide onboarding and training programs that teach customer acumen. So, as a sales leader, you need to encourage constant learning. You need events, interactive exercises, and, more broadly, you need to build a culture of customer-centric learning. But how do you go about building that?

Here’s one suggestion, and it’s something I’ve been thinking about for a long time: You need to rip the bell (or gong, or whatever you use to celebrate) out of the sales team floor and move it over to customer success. And the only time salespeople get to ring the bell is when their customers achieve success with your product – not when they close a deal. For Drift, that might be when a customer has their first conversation, or better yet, their millionth.

The idea here is that you shouldn’t be celebrating a signed contract. Because at that point, your company hasn’t delivered anything of value yet. As sales leaders, we should be training our teams to celebrate customer success, not contract signatures.

Sales Hiring

Play #34: Focus On The Qualitative (Not Just The Quantitative)

Jill Rowley By Jill Rowley

When evaluating candidates for positions within your sales organization, it’s easy to become obsessed with the numbers. How many deals did they close? How much revenue did they bring in? How often did they meet (or exceed) their quota?

But if that’s all you’re focusing on during the hiring process, you’re missing the bigger picture.

To make the best hires possible, you need to look at the qualitative characteristics of candidates, not just the quantitative. You need to consider their attitudes because you can’t afford to have a pouty Paul or negative Nancy on your team. They’ll sap your team’s productivity. And, above all else, you need to avoid hiring assholes, who will inevitably poison your organization.

A lot of leaders have made this mistake. They hire some hyper-aggressive rep to come in and close a bunch of deals, and they end up completely destroying the culture. You can’t have that.

In addition to looking at the numbers, you need to pay attention to integrity, coachability, curiously, grit, tenacity, and resilience, because these quantitative characteristics will be crucial to a new hire’s future success. Remember: Sales is hard. And at hypergrowth companies, it’s even harder. Attitude goes a long way, so you need to make sure you’re screening for that.

Play #35: Ask Candidates About The Last Time They Missed Their Number

Josh Allen By Josh Allen

One question I love to ask sales candidates is, “What happened the last time you missed your number?” And then I dig deeper by asking, “Why do you think it happened?” and, “Did you change anything about your process as a result?”

I love this line of questioning because it reveals if a candidate is a “thumb person” or a “finger person.” Here’s what I mean by that:

A “thumb person” points to himself or herself when something goes wrong and takes responsibility. They own the failure. A “finger person,” in contrast, is quick to point the finger at someone else or at some set of extenuating circumstances. They place the blame for the failure elsewhere.

When I ask why they missed their number, finger people tend to say things like, “marketing didn’t give me enough leads,” or “my territory sucked,” or “the SDR I was working with was terrible.” So you get this litany of excuses.

With thumb people, they admit up front that they did something wrong and explain what they learned from the experience. For example, they might say, “You know what, I realize that I had put two deals into one basket and without those two deals I wasn’t going to be able to get to my goal, and instead of spending the time to drive other opportunities, just in case those two deals didn’t work, I was spending all my time on those deals.”

When hiring, I want to know: Is this someone who’s going to take ownership of their mistakes, or are they going to point the finger somewhere else? This gives you great insight into somebody’s mentality and their ability to be resilient and to problem-solve if something’s not working. Because at the end of the day, you need salespeople who will take ownership and responsibility for their quota instead assigning blame somewhere else.

Play #36: Ignore The “Would I Have A Beer With This Person?” Benchmark

Josh Allen By Josh Allen

This is a common hiring mistake I see sales teams make: They prioritize hiring people they like, as opposed to seeking out the best people possible.

I had a manager in the past who used to say, “One of the things I want to gauge is whether or not I want to have a beer with them.” But here’s the thing: That doesn’t tell you anything about whether or not they’d be good at the job.

As a sales leader, you need to push aside your confirmation biases. You may find yourself liking candidates because of the school they went to, or the company they worked at before. I know this has happened to me. In the past, I fell in love with the company someone worked at before. I wanted to hire someone who was at Google for four years and did a certain thing there, and had exposure to a company that is considered best in class. But in isolation, that’s a bad reason to make a hire.

To make the best hires possible, you need to remove as much subjectivity as you can. You need to be consistent and ask the same questions you ask everyone else. That’s how you create an objective, repeatable process for figuring out if someone is a good fit for a role and a good fit for your company’s culture. As an interviewer, you need to represent your team and ignore your individual preferences.

Working With Other Teams

Play #37: Focus On The People

Jill Rowley By Jill Rowley

Sales is a people-based function. It’s all about connection and relationships, trust, and empathy. HR is the people-centric part of your organization. It’s all about finding, recruiting, developing, and retaining the excellent people you need for your sales team. You need to cultivate a strong relationship with your HR team.

Behind every successful company is a team of people who share a vision, a mission, and a set of values. You need to create that same kind of unified dynamic in your sales team. This doesn’t mean everyone needs to be the same (far from it). It means you need to make sure that each person you hire is someone your customers will want to buy from.

A salesperson is not a commodity. You can’t just swap one for another and expect the same results. There has to be a solid fit in terms of aligning with your customer and your approach to sales. Just because a candidate was booking 200% of quota at another company doesn’t mean they will see that same success with your company. Every situation is different.

You can support and influence a salesperson’s integration and growth through onboarding, training, and development, but only to a point. Hire someone with the wrong skills, personality, or mindset and you’ll find yourself in a hole you can’t dig your way out of.

It’s also important to work with HR to build and standardize processes for interviewing, hiring, and managing people; but the smartest, most effective thing you can do is hire people who are passionate about your customers. It’s a nice bonus if they are also passionate about your product and your company, but it’s exponentially more important that they genuinely care about your customers.

Play #38: Align Sales & Product Around The Customer

Josh Allen By Josh Allen

The key to a strong and positive sales / product relationship is empathy. Sales needs to have empathy for product. Product needs to have empathy for sales. And – most importantly – sales and product need to have empathy for the customer.

What keeps many companies from figuring this out is the undeniable fundamental differences between the way salespeople and product people think and work. It’s like the whole Mars / Venus thing. Often times they’re speaking a slightly different language.

There’s also a pretty big cultural component to how these two teams work together, which is why this partnership needs to be built at the leadership level. The right approach to collaboration will depend on the business model. What’s driving the company – product or sales?

The truth: you need both.

When sales and product are siloed, it creates a huge disconnect that puts both teams at a disadvantage. Instead, you want to meet in the middle by focusing on the customer. Ditch the egos and forget about quotas. The way forward is about uniting on the data and what’s best for the customer.

Sales can help by collecting customer feedback for the product team, but don’t stop there. You don’t always have to be the middleman. Encourage the Product team to participate on customer calls. That helps them build empathy for the customer and can also boost your company’s credibility.

Also, never underestimate the power of presenting customer concerns / requests using specific examples and customer names. Asking how you can help Sally achieve her goals not only makes the issue very tangible, it also shifts the focus onto the customer and away from internal power struggles.

Play #39: Treat Operations As A Strategic Partner (Because It Is One)

Jill Rowley By Jill Rowley

Operations is the team that can help you understand the customer journey, inside and out. They have the data intelligence you need to set sales goals and quotas and develop the strategies to meet them. You literally can’t plan without ops.

Operations owns three key areas:


This covers everything inside the customer journey – the prospecting triggers, demos you’re giving, opportunity and proposal processes, and so on (and on) – as well as the internal, behind-the-scenes cogs and wheels that drive the machine. Ops’ goal is to make the customer journey as smooth and efficient as possible, for both customers and sales reps.


Their in-depth understanding of the inner workings of process makes Operations eminently qualified to coach salespeople to be as good as possible at their jobs. This is an offer you shouldn’t refuse. Ops can help you reverse engineer a detailed plan to hit 120% of your OTE by helping you figure out how many demos and how much pipeline you’ll need to hit the mark based on average sales cycle and deal size and other variables.


Finally, bridging the gap between process and performance is analysis. Operations analysis skills come to the rescue when you’re seemingly doing all the right things, but not getting the desired results. They work with you to uncover what’s broken and how to fix it.

A productive working relationship with operations requires that you take a proactive role. Don’t wait for Ops to spoon feed you the answers. Raise your hand. Ask for what you need. But don’t treat Ops like a servant. They are a strategic partner. You’ll achieve more working together.

Play #40: Level Up Your Game With Sales Enablement

Jill Rowley By Jill Rowley

Sales teams are always having to adapt and step up to new challenges. From quarter to quarter and year to year, you don’t run the same plays. You need to level up your game and change up your strategy. This is where Enablement comes in.

Enablement provides the coaching, training, role-playing, and skill-building Sales needs to execute on new directives. Often underfunded and sometimes referred to as “the VP of Broken Things,” Enablement is actually a critically important part of the organization because they are really in the business of buyer enablement – helping you help the buyer to make a decision and sell that decision within their own organization.

Because more does not equal better. More demos will not necessarily deliver increased conversion, but better demos will. The salespeople who see the greatest success with Enablement are the ones who are brave. They aren’t afraid to try the new things Enablement suggests. They learn faster, are open to coaching, and measure performance based not on how they feel, but on how the customer responded.

Salespeople who thrive in partnership with Enablement are also able to get out of their own way by focusing on the moment and the customer, not on outcomes like commissions, quota, or performance accolades.

Play #41: Develop A True Partnership With Marketing To Deliver The Best Journey For Your Buyers

Jill Rowley By Jill Rowley

The age-old rift between sales and marketing is a given in most organizations. These two teams are used to being pitted against each other, but their rivalry doesn’t serve anyone.

Most companies try to overcome this challenge by working to create “alignment” between the two functions. Spoiler alert: Alignment isn’t enough. What you really need is true partnership. Alignment is two parties working independently along separate tracks toward the same goal. Partnership is two parties actually collaborating in a single effort.

Companies focused on alignment optimize around the “perfect hand off,” but buyers don’t want to be handed off. They want cohesive and seamless experiences.

How do you get there?

  • Put the customer at the center of everything. It’s not about sales or marketing. It’s about how sales and marketing can work together to facilitate the buying journey for the customer.
  • Have the same goals. This seems like a no brainer, but it’s easy to start chasing different things. Ultimately, you’re all working to increase customers’ willingness to buy from you again and advocate for you.
  • Plan together. No secret counsels. Develop an approach that is essentially a waterfall – each function feeding the other, and everyone understanding their own and their partner’s responsibilities.

Doing all of this will allow you to tackle challenges as a coordinated team and overcome issues with more speed and grace.

What are you waiting for? Someone has to extend the olive branch. Why not you? Sit down with your counterpart, find out what matters to them, and where your goals intersect.

Play #42: Respect Finance’s Role In Protecting The Company

Josh Allen By Josh Allen

The biggest mistake sales teams make when working with Finance is failing to understand why the Finance team makes the decisions it does. Too often, salespeople – who are hyper-focused on booking deals and hitting their numbers – think of Finance as the “order prevention team.” They assume Finance is out to get them with red tape and inflexible protocols.

What salespeople need to understand (and respect!) is that the core responsibility of the Finance team is to protect the company financially. They are the ones tasked with the unenviable task of crossing all the t’s and dotting all the i’s to ensure that any potential financial risk is mitigated and that all financial matters are handled in a way that is most beneficial to the company’s long-term success and health.

Sales typically works with Finance in two primary areas. During the sales process, it’s all about terms and contracts. And, on a more personal level, Finance plays an instrumental role in building and fulfilling compensation plans.

Whether you’re working with Finance on the finer details of a critical contract for a new piece of business or navigating the complexities of a multi-tiered compensation plan, things will go much more smoothly if you are willing to step back and take a moment to look at the big picture.

To work well with Finance, you need to understand not only the rules, but the “why” behind the rules. When you can couch your conversations in this understanding, it’s much easier to find ways to work together that are more flexible, which often include various shades of gray, and ultimately work for you, your customers, and the company.

Play #43: Give Legal As Much Context As Possible (Then Let Them Do What They Do Best)

Josh Allen By Josh Allen

Just like Finance, Legal’s first loyalty is to the company. Their job is to do what has to be done to mitigate risk. Their responsibility is to flag anything that looks like it might be a problem, and deal with it.

Salespeople mostly interact with legal over customer contracts. This can be a frustrating and even frightening experience to the uninitiated. I still remember the markup on my first red-line deal. I thought the deal would never happen. I quickly learned, however, that that’s a very normal part of the process. There was no need to freak out.

The truth is that your Legal team wants to help you land the deal. They just have to do it their way, making sure that they can deliver a contract that is good for the customer and the company.

You can help everyone meet in the middle by getting some basics under your belt. Take the time to educate yourself about what’s written in stone and where you may have more flexibility. This will keep you from wasting your time (and Legal’s) pushing for the wrong things.

The best thing you can do is provide Legal with as much context and detail as possible, and then let them do what they do so well. Just like the sales process, the legal process is all about anticipating and overcoming objections. Make sure your Legal team is fully briefed on everything they need to know about the customer, what they’re buying, the value of the deal, any sensitive issues, what it would mean to the company if you close the deal, and so forth.

If you have such insights, it’s also really helpful to share any existing contracts that may be a good example of the kind of deal you’re working on.

In short, give them the whole scoop, and then let them do their job.

Play #44: Do Your Homework Before Bringing Your CEO Into The Mix

Jill Rowley By Jill Rowley

Having the CEO or founder involved at the opportunity, deal, or account level can make Sales’ job easier. After all, people at the leadership level have the power and resources to make things happen. They’re the most visible, with the most name recognition. However, they are not a silver bullet. You need to be selective and strategic about when and how you involve them.

The CEO is not your prospecting partner. It’s not their role or their responsibility to open doors to help you break into accounts cold. They have a company to build and a vision to fulfill.

CEOs and founders are most typically looped into the sales process to help reduce friction. This might be early in the conversation, or later after the buyer has become a customer. Sometimes, their presence is intended to send the message that your organization is committed to putting the customer first. Sometimes, the goal is simply to create a “soft connection” that may come in handy later on when something inevitably goes wrong and needs to be smoothed over.

In either scenario, your job as the salesperson is to put in the legwork and do the due diligence to make the CEO’s job as easy as possible. Start by reading them into the situation so they understand the specific context and why the opportunity is so exciting. Provide as much detail as possible about the customer, the deal, your progress to date, potential roadblocks, potential opportunities, and – most importantly – exactly how you’re hoping they can help.

If the ask is to help reaching out to a potential customer, do your homework. Research by reading articles and listening to podcasts – whatever it takes to get the full 411. If you want the CEO to send a note, write it yourself. They may not always use it, but at least you took the initiative.

Finally, don’t approach the CEO only when you need something. That’s just tacky. Make the effort to build and maintain an ongoing relationship with them so that when you do reach out, it’s not coming out of left field.

Play #45: Work With Customer Success To Get Your Customers Started On The Right Foot (Don’t Just Hand Them Off)

Josh Allen By Josh Allen

Contrary to popular belief, the customer’s story doesn’t end with the sale. Unfortunately, the traditional approach to how Sales and Customer Success work together is based on the “handoff” model, which can create a less-than-positive customer experience.

The thing is, no one wants to be “handed off” from department to department. Customers want relationships they can depend on with people they can trust. While it’s not possible to give every customer a dedicated “cradle-to-grave” advocate, there are things you can do to create a more customer-centric experience around the transition from prospect to customer.

Sales can help customers prepare for life after the contract signing by looking at things through a Customer Success lens. What comes next for the customer? What does the onboarding process look like? What kinds of resources are available? What are their next steps? Don’t leave a new customer hanging. Help them get started on the right foot.

Customer Success can provide Sales with critical insights into customer profiles. They know what successful customers look like (and what makes them successful). And they know which customers to run from.

The optimal partnership between Sales and Customer Success balances a separation of church and state with a deeply collaborative dedication to the customer’s best interests. A blended Sales / Customer Success role can create a conflict of interest, so best to steer clear. Siloed Sales and Customer Success functions result in a disjointed experience and operational ambiguity that causes things to fall through the cracks.

The best solution is to define each team’s focus and responsibilities clearly up front, and structure their roles to allow for seamless collaboration. The customer should feel like they have a closely integrated team including an expert on the product side (onboarding, optimizing, etc.) and an advocate on the business side (contracts and so forth).

Sales Experiments

Play #46: Fence Off A Group Of Individuals Who Are Focused On One Thing

Josh Allen By Josh Allen

I think about experiments less as individual experiments and more as team experiments. Because the only way you can venture into something new is through teamwork.

For example, at Drift, we recently kicked off an experiment where we’ve dedicated people to sell into parts of Europe. We want to test the type of result we can drive with a concentrated effort selling to businesses that buy slightly differently from their US-based counterparts. The goal is to learn, within this focused team, the best way we should go to market longer term and scale the operation overseas. And you can use our same approach for any experiment you want to run. Here’s how it works:

Start by fencing off a group of individuals who are responsible for one thing. Have them be laser-focused on that one thing, with the objective of proving or disproving whether or not venturing into a new market, a new segmentation, a new product offering, a new way of doing things is actually something that you want to fully support in the business.

Instead of creating a cross-functionally funded segment, run it as an experiment. That means limited support from other business functions, unless you’re able to contain it within the experiment itself. Just keep in mind that you shouldn’t need to build anything from a product standpoint to support it. It has to be able to stand on its own, and you can use the feedback you get to understand whether or not it’s something you want to build out.

I’m a huge advocate of this type of experimenting. It’s something I did at LogMeIn and CarGurus and am now doing at Drift. What I love about these experiments is that there’s no success or failure: It’s all about learning. You learn one way or the other as a business whether you should invest in something or not invest in something, without suddenly moving the whole organization in a new direction just because you think there’s a chance it could work.

Play #47: Set Your Criteria Up Front

Josh Allen By Josh Allen

The most important thing to remember when designing a sales experiment: Set your criteria up front, attach yourself to it, and make sure you communicate it to your team. Specifically, you need to set the criteria as to what the experiment is, who’s involved, what the goals are / what you’re trying to achieve, and how long it’s going to run for.

The next step is to communicate all of that with the broader team so they know what’s happening. That way, you can remove the human tendency to move the goalposts halfway through an experiment and shift things around.

You need to have a good definition of the experiment up front before you run it, so it’s as close to scientific as you can make it. So whatever results you yield, you have enough statistical significance one way or the other to suggest it’s either a “go” or “no go” decision.

The Future of Sales

Play #48: Weave The Customer’s Point Of View Into Your Sales Process

Jill Rowley By Jill Rowley

Moving forward, the fundamentals of sales will be the same as they’ve always been: Those who serve the needs of their customers the best are the ones who will succeed. That’s what the sales profession is all about and will always be about.

That being said, the way in which you best serve your customers’ needs is changing. Customer expectations will continue to evolve, so your modeling of your ideal customers will need to evolve, too.

One of the things we need to do a much better job of is to stitch and weave the customer’s point of view throughout every facet of the business. This includes product, marketing, sales, customer success, education, professional services… everything. Only by stitching and weaving the customer’s point of view throughout that whole ecosystem will you be able to create a seamless customer experience.

In the future, the companies that create the best customer experiences are the ones that will drive the most revenue. Meanwhile, the companies that don’t optimize for experience will disappear.

Play #49: Make Video A Regular Part Of Your Sales Process

Josh Allen By Josh Allen

Apart from an in-person interaction, video is the only channel that allows you to read tone, body language, and to see the whole room and what’s going on.

Using video just makes so much sense in a sales process and it’s something that’s been around forever. But only now am I seeing it get introduced as a regular part of a selling and buying process. It’s not just about selling, it’s about when your buyers are interested in having a conversation or learning more. For example, Drift Video gives the buyer an opportunity to use chat directly from the video product to ask questions. Talk about an ability to get answers NOW!

☝️ That’s what the future of sales will look like. In the past, video wasn’t something that was widely used. But during this past year at Drift, I’ve seen how effective it can be. And now it’s crazy to me that we weren’t using video more at the past sales organizations I ran because it really helps create such a strong relationship between buyer and seller.

Play #50: Embrace Artificial Intelligence (But Don’t Forget To Be Human)

Josh Allen By Josh Allen

Sales will always require human-to-human engagement. That’s something that will never change. But what will change is that artificial intelligence (AI) will play a much bigger role in the funnel when it comes to buying.

Even in enterprise sales cycles, and more traditionally complex buying cycles, AI is going to start to play a bigger role because of the predictability of its performance and of the outputs it can generate. AI removes subjectivity and eliminates the peaks and valleys of human performance. It takes all of that out of the equation and you suddenly see, “Oh, wow, we can do the exact same thing every single time using AI to create a similar, predictable result.”

Over the next 10 years, AI is going to become more commonplace in both B2B and B2C contexts, and sales and marketing organizations will need to embrace it in order to keep up with the competition. With that said, humans will still be part of that last mile when it comes to selling. Why? Because people still genuinely want to buy from other people, and when they’re transacting through complex processes and cycles, they want to have that human element. They want to hear how another company that looks like them is using your product, and that’s often a story that gets told during introductions and during human-to-human networking.

So I don’t think the human part of sales will ever go away completely. But at the same time, AI will continue to inch its way down the funnel even further. You could argue Google is the ultimate top of the funnel AI: Buyers can do a search and get millions of returns in less than a second. That’s going to continue to narrow down so that as buyers interact with businesses through a chatbot, they’re going to get more and more of the answers they’re looking for before ever engaging with a human.

Final Thoughts

The more sales changes, the more it stays the same.

Despite the major shifts that have happened in what buyers expect, and how they prefer to communicate, the best salespeople still adhere to the same basic principles.

They act as helpers and guides.

They pull instead of push.

They attract instead of attack.

They listen more than they talk.

And instead of going for the hard sell, they dig deep into pain points, asking relevant questions and offering personalized solutions.

Chances are, you already knew all that, and you already have what it takes to excel as a sales professional. So our hope is that these 50 plays from Jill and Josh helped light a fire in your belly and helped show you how to make these timeless principles actionable.

Need more help taking your sales game to the next level?

Drop by and start a conversation with us. We’d love to chat with you.

– The Drift Sales Team

About the Authors

Jill Rowley

Jill Rowley

Jill is a partner at Stage 2 Capital and is an advisor to several high-growth SaaS companies. During her storied career, she’s also served as the Chief Growth Officer at Marketo, the social selling evangelist at Oracle, and the “EloQueen” at Eloqua (she was employee #13 and spent 10+ years there growing the marketing automation space). Before that, Jill was one of the first-ever SaaS sales professionals, working as an account executive at Salesforce, where she was named the #1 Mid-Market Sales Rep in 2001. You can connect with Jill on Twitter at @jill_rowley.

Josh Allen

Josh Allen

Josh joined Drift as Chief Revenue Officer in 2018 after serving as SVP, North America Sales & Service at CarGurus, where he led a team of more than 300 sales, service, and operations professionals during the company’s most expansive growth period. He also spent a decade at LogMeIn, where he held a number of leadership positions, including VP of Sales for two of the company’s three business units, and helped open and expand their international headquarters in Dublin, Ireland. You can connect with Josh on Twitter at @joshmallen.

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50 Lessons From Eloqua, Oracle, Marketo, CarGurus, LogMeIn & Drift