This is the series where we talk to GTM trendsetters about the strategies and tactics they use to drive results.
We recently talked to Sean Gentry, Senior Manager of Corporate Sales at Webflow, about empowering sales teams as part of our recent event: Human-centric prospecting in the AI age.
Here are three of the top takeaways from that conversation (check out the full recording above).
1. Tool up with the right tech
When Sean started in sales, landlines and whiteboards were about as technical as it got.
Times have clearly changed. Sales teams have lots of shiny tools to choose from.
But that doesn’t mean all revtech is created equal.
Sean’s must-haves? CRM, sales execution, data enrichment, call recording, and signal tracking.
Person360™Common Room’s Person360 feature allows you to deanonymize, merge, and enrich signals from every channel connected to Common Room. This makes it easy to reveal the identity, intent, and context of every buyer and customer.
Each tool plays a part in the sales process—from research to outreach—but signals are especially important for getting visibility into the buyer journey.
“At Webflow, we have Common Room [...] and the ability to be able to see where people are spending their time, where they're digging in and surfacing those insights, has been super valuable,” Sean said.
That goes double in the AI age.
“There’re so many people out there that are just getting absolutely blasted by AI and automation and people sending hundreds of thousands of emails,” Sean said.
Signals help sellers reach out to the right person with the right message at the right time. In a world where it's exceedingly easy for prospects to ignore their inboxes, signal-based selling gives you a way to break through the noise.
2. Buying signals are the new open rates
There was a time when email open rates were how reps prioritized their outbound.
Opens equal engagement, after all.
“At Outreach, we would have our reps filter by engagement,” Sean said. “So if you sent out 100 emails, you've got 15 people that open them in the last 24 hours, boom, that's your dial list right there. Those are the people that you're calling first.”
Today’s reps are still on the hunt for signs of engagement. Luckily for them, the data at their fingertips has gotten a lot more expansive: product usage, website visits, social engagements, open-source activity, community interactions.
That doesn’t mean you should build your outbound strategy around a single signal—a LinkedIn like isn’t the same as a demo request. But it does tell you which accounts and prospects you should start prioritizing, researching, and outbounding into.
RoomieAI™Common Room’s RoomieAI—a suite of AI-powered tools specially designed for go-to-market teams—allows you to augment your day-to-day workflows to boost productivity. This makes it easy to summarize account research in an instant, create LLM-generated outbound snippets based on every available signal, and much more.
And just because reps have a lot more visibility into buyer activity across channels doesn’t mean that they should lead with that. Authentic, value-based communications will always win out over telling someone you saw them on your website.
“I always joke with my team that you never want to be that person that sends an email that says, ‘Hey, I love what you've done with your living room furniture,’ like you’re looking in from their front yard,” Sean said. “You never want to be that person, but we know who to prioritize based off the people that are obviously engaging with our content.”
3. Make prospecting less lonely
Prospecting can be a grind. A difficult and sometimes lonely one.
That’s why Sean is big on group prospecting sessions.
“One of the best ways that I've seen to do it and motivate people is you take an hour block, you get everyone together, you have them prep their call lists, and for that hour you get everyone on the Zoom together and you're dialing down,” Sean said.
Cue the virtual high fives with every meeting booked.
There’s a reason group fitness classes are so popular. Doing anything tedious or difficult is easier when there are people cheering you on.
But just like a fitness class, you can’t expect insane results on day one. Strength training is a marathon, not a sprint.
“You're going to walk out of an Orangetheory class or get off the bike at a Peloton class, and you're not going to have a six pack, you're not going to be shredded, but you continuously do that over and over and over, and you're going to increase your fitness or your stamina or just your overall health,” Sean said. “And that's the same way with pipeline, right? You're not going to do one session and come out with 18 opportunities, but you continuously do this over and over and over, and that's what separates the great AEs from the people that are just at quota or are barely missing.”
These are just some of the takeaways from our conversation with Sean Gentry.
Watch the recording for the full story.
And stay tuned for the next edition of Go-to-market mavericks!
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