Hey everyone 👋
It’s that time again – I’m excited to introduce you to another member of the Drift team.
In this edition of Inside Drift, I think it’s high time you met Sam Boyd, Director of Sales at Drift. Sam has worked at Drift for two years and currently heads up our Drift Email go-to-market team. And when he’s not pumping up his team by playing the role of office DJ, you can find him on a bike or in the water training for his next triathlon.
Ready to meet Sam? Let’s go ⚡
Editor’s note: The following has been edited and condensed for clarity.
Kaitlyn Martins: We’ll start with an easy one! Can you tell me a little bit about what you do here at Drift?
Sam Boyd: I’m a Director of Sales, and I currently work on our Email team. After about two years of working on the chat side of things, I moved over to email with the challenge of helping to build out our SKU as we look to add another communication channel into the Drift suite.
Kaitlyn: What does a typical day for you look like?
Sam: Things have certainly changed a bit since we’ve been out of the office (less music requests from the sales floor), but overall my days have pretty much the same structure. Ideally, I get up and get outside before logging on (I’ve been biking a lot which is a great way for me to start the day and clear my head). From there, my day is heavily focused around the go-to-market side of Drift Email with other product-focused meetings mixed in. Depending on the day, I’ll have a few 1:1’s with team members, a pipeline review or two, call review sessions with the sales team, and then find some time to focus on some larger initiatives.
Kaitlyn: Tell me a little bit about the Drift sales team. What is the structure, and what does a typical day look like for someone on your team?
Sam: The overall Drift Sales team is getting pretty big! We segmented out over a year ago now, which means we basically went from the Wild Wild West to a more structured approach where we align the sales reps skills and focus them 100% around a market that fits them. We use company size as the main differentiator (think about how a 50 person company would buy in comparison to a 5,000 person company) and then break out a bit further based on either product (e.g. Chat, Email, Automation, Video, etc.) or goals (e.g. account management).
A typical day for someone on the Email team is fairly similar to someone on our SMB (small business) or SME (small-to-medium enterprise) teams. They are responsible for following up on all their leads, booking their own demos, running discovery calls, and then managing a sales cycle to close. Layer in some weekly trainings and deal reviews, and the weeks can really fly by.
Kaitlyn: What type of skills and background do you look for when you are hiring someone for a sales position?
Sam: In our sales hiring process, we’ve done a great job assigning roles to the hiring managers so that we are all looking for specific skills or traits. I think the recruiting team has helped level us up here big time when it comes to understanding the skills the role requires and then finding the right candidates.
For me, I love meeting a candidate who has a deep sense of motivation to succeed. The kind of thing that drives them day in and day out. I like getting to meet someone who has a drive that is so deeply rooted that they are willing to push themselves no matter what. Beyond motivation and passion, there is no substitute for grit, perseverance, and a learning mindset. Show me someone who’s been through the ups and downs before, has come out on top, and can articulate how or why they were able to succeed. That to me is what makes a strong candidate.
Kaitlyn: What was your dream job as a kid?
Sam: Hockey player, all day every day ? In street hockey, I was always Cam Neely. I think by the time I turned 13 or 14, I realized that a career in the NHL wasn’t happening. Once I got over that, things started to take shape. I’d always admired my parents because they both started and run their own businesses. I didn’t necessarily want to dive into a family business, but I think that’s where a bit of the entrepreneurial spirit came from and that’s what has been driving me towards early-stage companies.
Kaitlyn: What is the best career advice you have ever received and where did it come from?
Sam: When I was making the transition from sales rep to sales manager, it was a real struggle. I went from being an individual contributor with a bit of success under my belt, and then got thrown directly into a management role (with very little training). I was used to owning my day, my skills, and ultimately my number. But when you move into management, all of that changes. You can’t own the same things you did as an individual when you’re responsible for a whole team. There was a point I was feeling low and struggling to shift my mindset and focus. Around that time, I spoke to a good family friend who has spent a lifetime in sales. After having a lot of conversations with them and soaking up endless wisdom, one piece of advice stuck out to me. It’s the idea that the work you put in today won’t be recognized today (and might not be fully recognized for a few months), but you’ve to play the long game. As a rep, I was used to looking for immediate gratification, but it turns out that’s the enemy of long term sustainable success. When I shifted my mindset toward playing the long game, it enabled me to build one of the strongest teams I’ve ever had the pleasure of working with. That’s something I’m really proud of.
Kaitlyn: What’s your favorite part about working at Drift?
Sam: THE PEOPLE! I get asked about Drift all the time. Everyone wants to know what we’re doing or get an inside scoop on what we’re working on next, but ultimately what I end up telling everyone is that it’s the greatest place I’ve worked – and that’s all because of the people here and the culture we’ve built as a team. I feel so fortunate to work with some of the smartest, most driven, most interesting people, and I am lucky to learn from them every day. I’m a stronger employee and person because of the people I get to interact with at Drift, and to me, that’s priceless ?
Kaitlyn: How has your team stayed connected during this period of work from home?
Sam: We text a lot more than we did before. Slack is great, Zoom chats are ideal for some face time, but a lot of 1:1 or group communication takes place via text message or WhatsApp.
Kaitlyn: What’s something people don’t know about you?
Sam: I’m a mediocre triathlete, but I love it ? No Ironmans or anything like that (yet?) but about 10 years ago, someone challenged me to run a triathlon with them and ever since then I’ve been bitten by the tri bug. It’s forced me to focus on taking care of my body and health which I’ve prioritized a lot more as I’ve gotten older. Triathlons are a massive competition between you and only you and as someone who hates losing, it’s been great. I’ve also learned a ton from training and competing in them and have applied those learnings to my everyday life. Most people think the hard part is race day, but in reality, the day of the race you’ve already won or lost based on the work and commitment you’ve put into training leading up to that point. It’s actually a lot like sales if you think about it.
Kaitlyn: Last question – what makes Drift a great company to work at for people interested in launching or growing a career in sales?
Sam: I know I’m biased, but I don’t think there is a better place to build your sales career than Drift. The brand power, the momentum, the people, and the leadership team setting direction every day are all top-notch. Selfishly, for a salesperson, I think the biggest benefit of working at Drift is the ability to educate a massive audience on a challenge that thousands (if not millions) of people have – and then be able to sell the #1 solution for that issue. It’s an absolute game-changer.