How Sales Coaching Helps Leaders Build Scalable Sales Teams

Welcome back to People in Sales, the community hosted by SparrowCRM for real conversations about how sales actually works. The Spotlight Series is where we sit down with the people living it. This time, we talked with Thomas Waites, a sales coach, GTM advisor, and professional CRO for startups.

Thomas didn't plan any of this either. He was VP of Sales at a global SaaS company through a Series A and an acquisition, then came back as CRO to a company he had quietly advised the whole time. Ask how he got here, and the answer starts somewhere much smaller.

How did you find your way into sales?

He didn't choose sales, exactly. Fresh out of grad school, he joined an early-stage solar startup as its first employee, right as its outside sales teams started falling apart. He got pulled into fixing them, then ended up running them. Nobody handed him a playbook for building a sales team. He just watched what made people quit or stay.

What's a lesson you learned early in your career that still shapes how you sell today?

Empathy. That's the one he keeps coming back to, and it didn't come from a training program.

A single book did more for him than most sales coaching ever has: How to Win Friends and Influence People. Most sales training still centers the seller instead of the buyer, he says, and it shows in what actually moves the needle on performance.

You've built and led teams. What are your biggest lessons on leadership?

Two things stand out when it comes to sales leadership. First, vulnerability.

He used to think a leader had to look flawless to earn respect. Turns out the opposite is closer to true, and it's part of how sales leaders grow into CRO-level roles. Second, he splits every win across the whole team, not just the top performers.

Watch the Full Conversation With Thomas Waites

Hear Thomas Waites share his journey from early-stage sales leadership to becoming a Fractional CRO, along with his insights on sales coaching, AI in sales, and building high-performing teams.

What sales problem are you tackling in 2026?

Founders. Almost all of his clients right now are founders doing their own selling, which means he's often building the process and the team from nothing.

Founder-led sales doesn't leave room to ease into anything. Speed is the whole job.

What trends do you think are shaping the future of B2B sales?

AI, obviously. But he's skeptical of how unevenly people are actually using it.

He's watched people online claim AI is running their entire go-to-market motion. His honest reaction: he has no idea if they mean it, and he's curious to see how that plays out.

After the AI wave, how have your sales processes changed, and what's changed the most in how you sell?

Barely at all, if you're asking about the process itself. He still thinks selling is fundamentally a human-to-human thing.

That's a quieter take than the louder predictions about AI replacing sales jobs. Some companies have already swapped early demos for AI entirely. He hasn't, and doesn't plan to.

Which tools are helping you work smarter today, and what difference have they made?

Recording every coaching call. That one habit changed what he could do with his own knowledge.

He wishes he'd started years earlier, back when he was a newer sales leader running those same sessions with nothing to show for them afterward.

In an increasingly digital world, how important are in-person relationships and events?

Remote work already left people feeling disconnected, he says. AI adds a new layer of doubt about who's actually behind a message, which is exactly why he thinks in-person is about to matter more, not less.

What advice would you give to someone stepping into sales today, and to a budding sales leader?

To anyone just getting in, wondering whether AI makes the timing wrong: it doesn't. Learn how to get into sales anyway, because good sellers aren't going anywhere.

To a budding sales leader, his advice loops back to where he started: build a real coaching practice, not a training program wearing a coaching name badge.