Conversation Development Rep Of The Month: Meet 15Five’s Paul Whittington


Editor’s Note: Each month, we’ll feature a conversation just like this with a CDR to learn more about how they use Drift to book meetings. This is the sixth article in this series. Catch up on our interviews with Luminoso, Zappi, Bynder, Zaius, and Tenable in case you missed them.

15Five is a leading continuous performance management solution that not only guides employee growth and development, but empowers people to become their best selves. Through strategic weekly check-ins, 15Five delivers everything a manager needs to maintain visibility and impact employee performance, including continuous feedback, objectives (OKR) tracking, recognition, 1-on-1s, and 360° reviews. Over 2,100 forward-thinking companies use the solution to bring out the best in their people, including Credit Karma, WPEngine, and Spotify.

We chatted with Paul Whittington, a CDR or Conversation Development Representative, at 15Five. Paul is part of the inbound SDR team at 15Five, and he shared his experience with Drift, explaining his daily workflow, and offered excellent suggestions to get the most out of qualifying leads in Drift.

This conversation has been edited and condensed for clarity.

Akhil Dakinedi: How did you start using Drift at 15Five? What were your first impressions of it?

Paul Whittington: We started using Drift in January 2019. The SDR team at the time was about 7 employees, 2 inbound and 5 outbound. I was on the outbound team at the time. My first impression was that it was a little overwhelming, mostly because we weren’t sure how to effectively use it on the outbound side. But, once we started introducing ABM playbooks, we started to see how we could leverage those for our Account Executives, so that’s when I started to dive in deeper and add some of my accounts into Drift. Soon, I was getting notifications and was seeing prospects interact with my content. They were actually having conversations with me in Drift. The value of the tool became very straightforward from then on and I’ve been able to use it full-time ever since after moving to the inbound team in April 2019.

Akhil: How does Drift fit into your day-to-day workflow?

 Paul: I’m basically in Drift all the time. We have had a series of playbooks set up for various different pages of our website that trigger at different times for different people. We have two inbound reps here on the East coast and two on the West Coast, so Drift is basically monitored from 8am to 8pm ET every day by a sales rep. We recently did away with our demo request form on our website and replaced it with a chatbot, so that has caused the amount of leads that we get through Drift to increase significantly. Roughly 90% of the leads we’re capturing on a daily basis are in Drift, so all of our reps, myself included, are in Drift from the time they get to the office to the time they leave.

Akhil: How do you get new conversations in Drift?

Paul: We have a few different lead routing rules set up for who on our team gets the conversation. It’s typically done by the time of the day or what playbook it is. Basically, I get a notification whether it’s on my phone or my laptop that pulls me into the conversation and then I go in and try to respond to it as quickly as possible. Our team SLA is just under 30 seconds right now, so we’re trying to get in there and start these conversations as quickly as possible. Then we go through some basic qualification and set up a meeting with the AE. The system works well because everybody that wants to talk to us is being engaged with. As for everybody that falls off, we capture contact information and try to re-engage with them later. It’s been working out pretty well for us.

Akhil: What kinds of questions do you ask to qualify leads? Are there any common questions that they ask you?

Paul: 15Five is a continuous performance management solution. The majority of the people that we’re speaking with are HR leaders. So, basically, we’re learning about how they plan to leverage 15Five internally at their companies, how many employees they’re looking to roll this out to, and how they’re currently handling performance management. The questions that we get asked the most are around pricing and integrations. Things like different types of pricing plans and what integrations we do and don’t have, what is and isn’t possible there, etc.

Akhil: What’s your lead qualification workflow like? How do you hand off promising leads to your AEs?

Paul: Once we’ve run through our qualification questions and have determined that we are aligned, the next step is to figure out a time that works best for them. Then we check with our AEs and a calendar invite is on the table. Sometimes, if the lead isn’t available to chat right away, I’ll send them a link to my calendar through Drift Meetings, and if it’s during our offline hours, they will be automatically round-robined to a calendar of someone that can respond the soonest.

Akhil: Do you work closely with the person that builds your bots in Drift? How frequently do you update them?

 Paul: Yes. Joe is our Marketing Ops team member and the owner of our Drift account. He and I talk almost every day and are constantly making tweaks. He builds all of our bots. I occasionally build them, so we’re both exchanging information and sharing ideas or tweaks that need to be made on a daily basis. Changes to the playbooks are made on an ongoing basis as internal processes change or we identify some shortcomings or things that we can optimize and get better. Ultimately, if we decide that we want to add a new bot, that might be a quarterly conversation. Our bots are being updated on an ongoing basis.

Akhil: Do you have a monthly quota that you have to meet?  

Paul: Every rep on the inbound team has a monthly quota of 21 qualified opportunities. Prior to our demo request form becoming a Drift chatbot, those forms would come in and we’d respond to them as quickly as we could. We would sequence them in Outreach and then start calling them. Now, we’re able to talk to those folks in close to real-time, and it’s actually helping a lot getting to our goals sooner, which is starting a separate conversation around raising our goals. We’re able to engage with prospects in real-time and make that hand-off a little faster to the AEs. In fact, with the demo request bot, we’ve been able to increase our conversion rates for Sales Accepted Leads (SAL) to pSQL (pre-Sales Qualified Leads) from roughly 13% to 60%. The team is pumped about that.

Akhil: Are there specific things in Drift that you find yourself using a lot?

Paul: I like being able to see the lead details on the right side of the screen: their profile, their account in Salesforce, and their LinkedIn data. All of that is incredibly helpful to us. During conversations that’s kind of where I live, so I need to make sure that the person I’m talking to is not involved in a conversation with someone else. You never know when another outbound rep is calling them. I try to look at their LinkedIn during the conversation, see what their title is, and if there’s anything on their LinkedIn that might resonate with what 15Five does. Or at the very least, I look for somebody that is trying to become their “best-self” or wants to coach employees to become their “best-selves,” which we encourage at 15Five. Taglines or buzzwords like that are things that I’m looking for to help me better engage with the prospect.

Akhil: What’s your day-to-day like outside of Drift? Do you use any other tools in conjunction with Drift?

Paul: On the outbound side, reps are using tools LinkedIn Sales Navigator, LeadIQ, as well as Salesforce and Outreach to do some of their own prospecting and engage with their prospects. On the inbound side, I would say close to 85% of our day is spent inside of Drift because that’s where our leads are coming from. When we’re not in Drift, there are leads coming through things like our partner channels, where they’re sending us referrals, or we have leads are coming through the email address. On the outbound team, we’re spending a little bit of time qualifying leads outside of Drift, but on the inbound team, the vast majority of our day is spent in Drift. When we’re not in Drift and we’re not qualifying new leads, we tend to work some of the colder leads that we have by calling and emailing them through Outreach.

Akhil: Do you have any best practices or pro tips on how to get high-intent leads through Drift?

 Paul: Be quick to respond, and be quick to engage the prospect. Be as conversational as you can and distinguish yourself from the bot. Introduce yourself as a human. But also bringing some of your own personality, you don’t want to sound uber professional, but you don’t want to seem like you’re texting your best friend. You just want to be as conversational as you can. Add some of your personality in there –it will help put the prospect at ease and make them feel comfortable talking to you.

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