How Rachel Roberts (CRO) Went from $50 to $250 Million ARR

When transformation hits a revenue organisation, it's rarely smooth. But according to Rachel Roberts, Chief Revenue Officer at Level Access, that messiness is exactly where meaningful progress is made.

With a track record across marketing tech, cybersecurity, and enterprise SaaS—from Adobe and Cisco to high-growth firms—Rachel joined the SaaS Sales Performance Podcast to share her battle-tested playbook for leading transformation in high-stakes sales environments.

Here are the highlights 👇

🎯 It’s Not About Process – It’s About People

Early in her career, Rachel tried to implement a new sales methodology at scale—and it flopped.

“The mistake I made? I focused on the process, not the people.”

What she learned: teams don’t resist change itself, they resist change that doesn’t make sense to them. To drive adoption, leaders need to connect change to real, everyday problems reps are trying to solve—and make it feel relevant.

🔎 Find the Key People Of Influence, Not Just the Managers

When rolling out transformation, Rachel taps into informal leaders—the respected voices inside the org that others naturally follow.

“McKinsey shows transformations are 8x more likely to succeed when key influencers are involved. That checks out.”

Those early adopters become internal case studies, creating a ripple effect of buy-in through peer-led momentum—not top-down mandate.

📣 Celebrate the Right Wins, Repeatedly

Rolling out a new solution-selling motion? Then stop celebrating bluebird wins and transactional deals in your all-hands.

“If your rewards contradict your message, your team will default to what gets them praise.”

Rachel ensures every function—SDRs, hunters, post-sale teams—gets spotlighted when their wins align with the change being driven. The result: consistency between messaging and motivation.

🧭 Adjust the Rudder Without Losing Trust

Transformation isn’t one massive leap. It’s a series of adjustments—"tweaks to the rudder"—as markets, products, and data evolve.

But transparency is key.

“I’m the worst poker player. I tell my teams what’s keeping me up at night. If we get it wrong, we admit it and fix it.”

This honesty builds credibility and trust—so when the vision shifts, the team follows without fear.

👥 Use Small Cohorts for Real Listening

Massive town halls don’t drive dialogue. Instead, Rachel uses small cohort town halls (like regional pods or role-based groups) to get genuine feedback and answer real questions.

To ensure quiet voices are heard:

• Submit questions in advance
• Allow moderated anonymity
• Directly invite less vocal team members to contribute

This creates psychological safety—and surfaces signals from the field that help guide strategy.

📈 Balancing Quick Wins with Long-Term Vision

In the first 90 days, a CRO is under pressure to deliver—but Rachel balances urgency with patience.

Rather than overload the team, she staggers transformation in phases:

1. First, realign segmentation and go-to-market structure
2. Next, optimise compensation and goal-setting
3. Then, introduce a new methodology—at the right time

“We swapped annual goals for two six-month goal periods—so we can spoon-feed transformation and keep teams engaged.”

💡 Vision That Actually Lands

Rachel has a 3-part test for effective vision setting:

1. Stretch: If your top performers aren’t a bit intimidated, it’s not bold enough.
2. Clarity: If a rep can’t explain the vision to their family in 30 seconds, it’s too complex.
3. Connection: It must tie to what drives your reps—winning and solving real customer problems.

👋 And Yes, Some Won’t Make It

Transformation means levelling up. That requires top-grading the team.

“If someone won’t get in the boat—if they’re rooted in the past—you need to make respectful exits. Fast.”

While painful, this clears space for those aligned to the new mission and gives the team momentum.

Final Word: Transformation Is Constant

Rachel closed the conversation with a reminder all CROs need right now:

“Transformation is never going away. Markets shift. Buyers evolve. Tech moves. So we have to keep adjusting.”

And if your organisation builds trust, transparency, and a culture that rewards progress—your teams will not only survive transformation.

They’ll own it.

🎙️ Want more interviews like this?
Subscribe to the SaaS Sales Performance Podcast or check out Uhubs – the performance platform helping CROs coach teams, spot A-players, and roll out winning change at scale.