8 Ways to Start Better Conversations with Your Buyers

By Elizabeth Hilfrank

Knock, knock.

Who’s there?


Water, who?

Water you doing delivering unpersonalized experiences to your buyers? It’s the Revenue Era — where everything starts with a conversation!


Hey, it’s me, Elizabeth from Drift’s Podcast Network 👋

You may have heard my voice at the beginning and end of the first eight episodes of Conversation Starters. There, I had the privilege of sitting alongside Sammi Reinstein as she talked with Drifters, customers, and special guests to learn how starting the right conversation accelerates revenue for your business.

On almost every episode, Sammi said, “I need to have a notebook and pen next to me to take down all these great learnings.”

Little did she know, I was doing just that.

After compiling my notes and applying them to my everyday work, it seems only fair to share the SparkNotes version of the season with you all. But in true high school teacher fashion, I encourage you to go back and listen to the full episodes to get the most out of them.

Ready to learn? Here we go 📚

1. Use the Information You Have at Hand in the Right Way

Season 1 of Conversation Starters kicked off with Drift’s own VP of Productivity, David Kim. David has been in the sales enablement space for a while now, and in our pilot episode, he shared some of the best (and worst) personalization examples he has seen used in sales outreach.

The main takeaway?

Being personalized in your outreach isn’t creepy. When you leverage buying data and do research into your prospect, you show that you care about what that prospect cares about. And with that information, you can more clearly articulate how you can help them reach their goals.

2. Show Me That You Know Me

In Episode 2, content marketing expert Sarah Frazier shared what she has learned about creating personalized marketing campaigns through content.

Her key to success? Strategy.

Buyers are intelligent, and they know when they are being sold to. So, don’t try to fool them. Instead, play to the buyer’s strengths and show them that you’ve done your research, that you understand their pain points, and that your content will help them solve their problems.

3. Infer, Then Personalize

For Episode 3, Sammi doubled down on how websites specifically spark conversations. She brought in Guy Yalif, Co-founder and CEO of Intellimize — a platform that marries machine learning with marketers’ creative ideas to optimize web experiences — to help her out.

Through his work at Intellimize, Guy has seen many different approaches to personalizing website experiences. But the one that he keeps coming back to is the power of inference.

With this approach, you meet the buyer where they are and when they are thinking about you. Even the page a prospect is on can tell you a lot about their intent. So, infer what your buyers want and incorporate that into your outreach.

4. Test, Test, Test

At STANLEY Security, a global division of Stanley Black & Decker, Jacob Schneider is the Global Digital Experience Analytics Manager and in-house Drift expert. He joined Sammi for Episode 4 of the podcast to talk about using data to iterate on marketing campaigns.

Jacob has been instrumental in building out STANLEY Security’s Drift strategy — not only locally but (as his title suggests) globally too. The biggest thing he stands by when it comes to starting conversations is A/B testing.

Jacob and his team A/B test to make sure every conversation resonates with the site visitor, no matter where they are located. And if you have any doubts about how valuable A/B testing is, just know it’s something they’re doubling down on this year.

5. Open a Loop with Your Subject Line

After diving into data, Sammi circled back to the creative side of conversations for Episode 5 with Eddie Shleyner, Founder of VeryGoodCopy, a copywriting and content marketing resource.

Being a newsletter writer, Eddie knows a thing or two about email. So, in this episode, he shared some of his best tips to improve open rates.

Eddie pointed out that people should think about writing an email in the form of a loop. The subject line should open an information loop that can only be closed by reading to the bottom of the email. By putting your value proposition in the subject line, you can easily get your readers curious enough to open your email and read it all the way through.

6. Take the Extra Step for Feedback

Episode 6 of Conversation Starters was an inward look at the relationship between Drift’s sales and customer success teams. Enterprise Customer Success Manager Jaclyn Van discussed some of the biggest lessons she has learned about partnering with sales in over three years at Drift.

What code did she have to crack to satisfy her customers?


Jaclyn learned that customers will only thrive when both internal and external communication is clear. Her advice: When in doubt, overcommunicate. And don’t be afraid to ask your internal team for more information.

7. Make Selling a Team Sport

Ryane Bohm, Product Marketing Director at Gong, joined Sammi for Episode 7. In the episode, Ryane explained what a revenue intelligence platform really is and how using one can help companies build trust with their buyers.

While Ryane strongly believes in the power that data has to connect sellers with buyers and accelerate deal cycles, at the end of the day, she believes bringing in a human element will truly seal the deal.

For that, Ryane suggested bringing your team members onto the call — be it your manager, a VP, or an engineer with product expertise. By selling as a team, you can reinforce your expertise and show the buyer that you and your company are invested in them.

8. Find Trends in Feedback

Season 1 of Conversation Starters concluded with the 2021 World Champion of Public Speaking, Verity Price.

While Verity is the world champion now, public speaking and speech writing didn’t always come easy for her. In this episode, Verity told Sammi how she learned to set aside her ego and accept feedback where appropriate.

By filtering and finding patterns in the feedback, Verity figured out what areas of her speech writing and presenting she needed to spend her time on. Taking this approach made the feedback feel less overwhelming and helped her improve on the areas she needed to most.

Anxious for more? Good news. We’re already recording for Season 2 🎙️ Make sure to subscribe, so you don’t miss the release.

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