Build High-Performance Sales Teams

In an era where AI startups are dominating the growth narrative, the rest of the SaaS world is being forced into a different kind of evolution: transformation. That’s the world Jamie Lee, former Chief Revenue Officer at Zesty, has lived in. With 25+ years of experience across Silicon Valley tech giants and PE/VC-backed companies, Jamie’s perspective on what actually drives sustainable revenue growth is rooted in firsthand transformation.

On the SaaS Sales Performance Podcast, Jamie joined Matt Milligan to share hard-won insights on frontline leadership, the power of OKRs, the myth of “no time to coach,” and how the hiring bar must evolve if companies are to keep up with the pace of change.

Here are the key takeaways.

1. The Frontline Manager Bottleneck: Coaching vs. ‘No Time’

In every enablement discussion, a familiar phrase emerges: “We’d love to coach more, but we just don’t have the time.” Jamie doesn’t buy it.

“If I have five AVPs and the best one makes time for coaching and numbers, that’s the data set I need. Everyone else can do it. They’re just choosing not to.”

The bigger issue, he argues, is a lack of confidence in coaching. Many frontline leaders were promoted based on quota-crushing performance, not people development skills. As a result, they default to forecasting, deal reviews, and staying “in the business” — never making the leap to being “on the business.”

2. Coaching Culture Starts with Inputs — and OKRs

So how do you shift from a reactive culture to a developmental one?

Jamie’s advice: use OKRs (Objectives & Key Results) as a forcing function. But don’t keep them at the executive level. Pull your team offsite and co-create them together.

“When the team helps define the objective, the KPIs, and the actions required, they own the outcome. You get the buy-in, the behaviour change, and the alignment — all in one move.”

Sales leaders often underestimate the power of collaboration in goal-setting. But when reps understand how their daily actions ladder up to team-wide outcomes, peer-driven accountability starts to kick in. Lone wolves become team players.

3. Growth Mindset ≠ Lip Service

Many reps say they want coaching. Few truly act on it.

Jamie’s approach is refreshingly simple: assign a development task, then see what happens. Did they read the book? Did they watch the podcast? Did they reflect?

“I give action items because I want to see intent. If they show up with no prep, that’s all the signal I need.”

It’s about evidence of ownership — not just talk.

As Jamie shared, he’s handed out hundreds of copies of Carol Dweck’s Mindset over the years. Why? Because it’s not enough to say you're coachable — you need to demonstrate it, repeatedly, even when it's uncomfortable.

4. When Reps Resist AI… Dig Deeper

Jamie also tackled a hot topic: how to lead more tenured reps who are reluctant to embrace tools like AI.

His framework is based on curiosity and challenge:

• Are they intimidated? Help them de-risk experimentation.
• Are they stuck in a fixed mindset? Show them how learning builds trust.
• Are they just disengaged? Give them short, clear tasks and evaluate follow-through.

And if there’s no willingness to lean in?

“Then maybe it’s time they found a different environment — one that actually motivates them.”

5. Hiring for the Future: Hungry. Humble. Smart.

If you want to avoid coaching challenges later, Jamie suggests you hire better now. His team uses a model inspired by Patrick Lencioni’s “Hungry, Humble, Smart” framework:

• Hungry – Do they have innate drive? Will they go the extra mile without prompting?
• Humble – Are they grounded and open to others’ views, or are they know-it-alls?
• Smart – Not IQ, but EQ. Do they read the room? Are they self-aware?

This model becomes a shared language across hiring panels, 360 reviews, even leadership development.

“Miss one of the three, and the team starts to break down. Great sellers and leaders have all three.”

6. Your Role as Leader: Be the Mirror, Not the Hammer

Perhaps the most powerful insight came near the end:

“Great leaders don’t tell people they’re not right for the role. They help them come to that conclusion themselves.”

By guiding your team with transparency, ownership, and feedback — and by removing surprises from your performance conversations — you empower people to grow or opt out. Both outcomes are wins.

Final Thought

Jamie Lee leaves us with a challenge: What if sales leaders were held to the same developmental standards as doctors or lawyers?

“Sales doesn’t have a regulatory board. But we should still master our craft. We owe it to our teams, and to the profession.”

This episode is a masterclass in people-centric performance. For leaders looking to evolve from tactical execution to true strategic leadership, Jamie’s playbook offers the path forward.

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