*This episode was recorded during our Soundcheck days — now proudly rebranded as GTM Insider.

In this episode of the Soundcheck we have Will Allred, Co-Founder and CEO of Lavender on the mic. Together with his team, they are helping over 30,000 people write better sales emails faster.

TL;DR

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In an era where inboxes are saturated and every touchpoint matters, Will Allred, co-founder of Lavender, brings a no-nonsense take on what true personalization means—and how to scale it effectively. In this episode of The Sound Check, Will pulls back the curtain on why most email outreach fails and how reps can shift their mindset to win more replies and better conversations.

Here’s what we learned from one of the most respected voices in modern sales outreach.

What Is Personalization, Really?

“If it doesn’t serve a purpose, it’s not good personalization,” Will states bluntly. The days of dropping someone’s favorite football team or job title into an email and calling it 'personalized' are over.

A personalized email should feel like it was “written for one person, with a clear reason why you’re reaching out,” he explains. That could be tied to their tech stack, hiring activity, or even a shift in company size. But it must link back to a pain point you can solve—otherwise, it’s just noise.

At Trumpet, our personalised microsites are designed to scale that 1:1 feeling across an account, letting reps tailor every touchpoint from first click to signed deal.

What If You Can't Find Anything to Personalize?

“You are finding things—you just don’t think you’re finding things,” Will insists. A quiet LinkedIn doesn’t mean there’s nothing to go on. Their job history, tech choices, and company trajectory offer huge insight into what they care about.

These subtle signals, when used correctly, can be built into strategic outreach or a sharp P.S.—especially when layered with a short, curiosity-piquing subject line. According to Will, emails with well-placed personal touches and shorter formats are still getting 1200% more replies.

Pairing that with Trumpet’s buyer engagement analytics lets you see who’s engaging and how, so your personalization is backed by actual buyer behavior.

Why Conversation > Conversion

Most sellers still treat emails like conversion tools. “The goal shouldn’t be to book a meeting—it should be to start a conversation,” Will says. “If I’m not ready, I’m not going to accept a meeting, but I might reply.”

He encourages teams to treat email like a dialogue, not a transaction. That approach creates more natural buyer journeys and sets you up for smoother conversions down the line.

This aligns with how Trumpet’s digital sales rooms function—giving buyers space to engage with your value proposition asynchronously, without pressure, and with shared context across teams.

Scaling Without Losing the Human Touch

With automation running rampant, personalization becomes your differentiator. But Will warns against “click-this-button” promises from generative AI tools. “If you're never taking time to research your prospect, you're capping your development as a rep,” he says.

His recommendation? Build workflows that guide reps through where to look, what to look for, and how to use it. Don’t rely on one 'personalize here' bracket in a template. “If you're not thinking like a buyer, you're falling behind,” Will adds.

With Trumpet’s mutual action plans, reps and buyers stay aligned post-outreach, turning interest into momentum while reducing friction in the sales process.

Multi-Threading: It Starts Below the Line

“One of the biggest tactical gaps right now? Messaging below the line,” Will points out. Most reps only focus on decision-makers, forgetting the growing influence of users and managers.

“Talk to folks below the line like a reporter—not a seller,” Will advises. Help them authentically, and use those insights to build better business cases when you eventually talk to leadership.

Trumpet’s collaborative workspace lets reps tailor content and messaging across buying groups, supporting real multi-threading instead of just CC’ing more names on an email.

It’s a simple mantra, but one worth repeating: “Efficient is seller-centric. Effective is buyer-centric,” Will says.

👉 Want to scale personalization without losing the human touch? Book a demo with Trumpet to see how we help modern sellers connect with real intent.