Shifting Mindsets to Scale GTM Success

Written by Jason Silverman, Former Business Development Leader at Peek 

Let’s be real 

Before I spoke at Outreach Unleash 2025, I was nervous. Despite my background in acting, stepping onto a stage as my authentic self—not as a character—was a whole different kind of vulnerability. But I quickly realized: I’m not alone. Many of us are navigating the very same challenges when it comes to rolling out change across teams, tools, and mindsets. 

The experience? Incredibly validating. 

Now that I’ve had some time to reflect, I want to share a few takeaways that hit me hard—especially if you’re in the middle of driving go-to-market transformation at your company. 

Why most change management fails (and what to do about it) 

When I stepped into my role at Peek, I knew we needed to evolve the way we sold—not just what we sold. Buyer behavior has changed. Expectations are higher. AI is shifting what “good” looks like across the funnel. But here’s the thing no one tells you: The hardest part isn’t deploying new tech or writing new sequences. It’s getting humans to change. 

Change is uncomfortable. It stirs up fear, resistance, even ego. And if you’re a RevOps or Enablement leader, you’ve likely seen how easily change initiatives can stall out when people feel like things are being done to them—not for them. 

That’s why I lean into one framework every time I need to bring people along: CAR — Creativity, Awareness, and Responsibility. 

Let’s break it down. 

C is for creativity 

AI is here. Automation is growing. And the sales landscape is shifting fast. That means reps can’t just rely on plug-and-play tactics. They need to get creative. 

Creativity doesn’t mean reinventing the wheel every day—it means encouraging reps to test, personalize, and iterate on what works. Give them room to experiment. If you want reps to go from order-takers to strategic advisors, they need to feel empowered to try. Sometimes, that means letting go of “perfect” and embracing progress. 

At Peek, we gave reps the freedom to pilot different Outreach sequences, templates, and snippets tailored to specific industries or buyer pain points. We tracked performance, shared learnings, and evolved together. The result? More ownership, better engagement, and higher-quality conversations. 

A is for awareness 

Change starts with self-awareness. When we rolled out new workflows in Outreach, we didn’t just drop a doc and hope for the best. We made space for reps to reflect on why the change was happening and how it would help them sell smarter. 

Think of it like this: You can’t coach what people don’t see. And you can’t shift behavior without surfacing blind spots. 

We ran team retros

We ran team retrospectives and brought in frontline feedback. By layering in awareness—of how deals progress, where gaps exist, and what “good” looks like—we created a culture of transparency and growth. 

Reps weren’t just being told what to do. They were being shown how their actions moved the needle. 

R is for responsibility 

Ownership changes everything. 

When I look at the most successful enablement initiatives I’ve been part of, they all had one thing in common: the people closest to the work felt ownership over the process. 

Responsibility doesn’t mean reps doing it all alone—it means setting expectations, giving clarity, and reinforcing a shared commitment to outcomes. At Unleash, I talked about the importance of empowering people to step into the driver's seat of their growth. Not just ride along. 

We did this by aligning everyone—RevOps, Enablement, Sales Leadership—on shared goals. That alignment built trust, consistency, and momentum. 

The power of emotional intelligence in a tech-first world 

Let’s not forget the human side. 

In a world where AI can write follow-up emails, route leads, and predict next best actions, empathy is your differentiator. And that doesn’t just apply to sellers—it applies to leaders, too. 

At Peek, we talk about being umbrellas for our reps. Our job is to protect them from external chaos, so they can focus on doing their best work. That means listening, advocating, and making space for people to show up fully. 

Emotional intelligence isn’t just a buzzword—it’s the foundation of team resilience. And when your people feel seen, heard, and supported, they’re more likely to embrace change. 

Scaling change starts with culture 

If you want scalable change, you have to invest in your culture. Period. 

Culture is what enables process to stick. It’s what drives adoption of new tools. And it’s what fuels performance—especially during periods of transformation. 

At Unleash, I met RevOps leaders, sales managers, and enablement pros from across industries. What we all had in common? A deep desire to build cultures that work for people, not just processes. 

We swapped stories about onboarding, experimentation, and even a few epic fails. And through it all, one truth stood out: 

“You can have the best tech stack in the world, but if your people aren’t bought in, it won’t matter.” 

That stuck with me. 

Key takeaways if you’re leading change: 

• Start with people. Technology is the enabler, not the driver. Build buy-in before rollout. 

• Empower experimentation. Let reps test, fail, learn, and share. Growth thrives in experimentation. 

• Make data visible. Use tools like Outreach’s conversation intelligence platform, Kaia, and pipeline management software to surface insights, spot gaps, and coach effectively. 

• Don’t skip retrospectives. Reflection is where real learning happens. 

• Lead with empathy. Change is emotional. Treat it as such. 

Final thoughts 

Change isn’t a one-time initiative—it’s a muscle. The more you build it, the stronger your team becomes. 

To everyone navigating GTM transformation right now: You’re not alone. And if I’ve learned anything from Unleash, it’s that community matters. Keep experimenting. Keep reflecting. And keep showing up with intention. 

Also, yes—I did make a dumb Cars joke during my session. 

KA-CHOW. ⚡️