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James Jackson didn’t take the conventional path into RevOps. He began as an engineer, pivoted into business development at Siemens, earned his MBA from Harvard, and entered tech through a frontline sales role at Microsoft—carrying quota during the early days of Azure and selling to giants like Tesla and Oracle.

His curiosity and drive to master the full revenue engine led him into sales strategy at Cisco Meraki, Sales Ops leadership during Docusign’s hypergrowth era, and now into his current role as Global Head of GTM Planning, Compensation, and Systems at Snowflake.

Because James has operated through some of the most volatile GTM shifts in recent memory—from COVID-era overperformance to the painful recalibrations that followed—his approach is grounded in pragmatism and we knew we had to interview him on The Sales Compensation Show.

In this episode he unpacks his lessons on aligning compensation with company strategy, restoring field trust after disruption, and designing GTM systems that can flex in fast-changing environments—including the challenges of consumption-based models.

If you’re leading RevOps through today's uncertainty, this episode is required listening! Below, you’ll find our top takeaways.

Catch the full show, plus our favorite insights below.

Episode resources

• Connect with James on ��
• , by James C. Hunter

Let company strategy drive the plan—not the opposite way around

Compensation leaders don’t set company strategy. But they do operationalize it. That’s the line James Jackson draws early in his conversation with Nabeil—and it’s a critical one.

“Comp plans do not set the strategy of the company. They should *express* the strategy of the company...we reconfigure ourselves to express that direction of ELT and get that done.”

James Jackson

Global head of GTM planning, comp, and systems at Snowflake.

Too often, organizations fall into a common trap: trying to use comp to create behavior before clearly defining the behavior they actually want. The result? Misaligned incentives, confused sellers, and plans that drift further from the company’s true goals.

James offers a sharp example from his time at Docusign. During the COVID boom, the company doubled its revenue in a year. Reps were over attaining, territories shrank, and headcount surged. The comp strategy matched the moment: reward speed, volume, and top-line bookings.

But when the macro conditions shifted, the same assumptions from before didn’t hold. Growth slowed. Pipelines inflated. Reps were still chasing hypergrowth in a market that could no longer sustain it. The comp plan, once aligned, had become a liability—fueling behavior that was now misaligned with the business’s actual needs.

This is where many teams go wrong. Comp plans must evolve with the phase of the business. In hypergrowth, it’s about net-new logos and volume. In post-hypergrowth, it’s about efficiency, retention, and sustainable expansion. If the business pivots, the plan must too.

The key lesson? Don’t ask comp to fill a strategic vacuum. Before you model a single plan, clarify your company’s strategic priorities. Is your goal net-new ARR, multi-product adoption, retention, or margin improvement? Only then can your comp design reinforce the right behaviors.

For RevOps leaders, this means starting upstream: align with the ELT on what success looks like—and build (+ model!) plans that turn that vision into measurable action in the field. Every compensation lever should reinforce the overarching direction.

When plans need to shift, reach for simplicity

James also knows that in moments of disruption, perfect models don’t help. Actionable proxies do. James shared one such proxy he used at Docusign. ��

After doubling headcount based on historical overperformance, Docusign was left with bloated coverage and misaligned quotas. James needed a way to right-size the GTM structure fast. To help leadership quickly assess whether rep coverage and cost structure still made sense, James developed a simple but powerful tool to compare productivity across reps and segments: ACV divided by OTE. ��

As he explains, this became a “poor man’s LTV-to-CAC”—an efficient, accessible signal of where the business was overextended and where to pull back. It didn’t require perfect data. It required clear thinking. And in high-pressure moments, that’s often the difference between paralysis and progress.

For RevOps leaders operating in volatile markets, this is a valuable mindset: don’t chase complexity. Build fast, directional tools that help the business course-correct in real time.

Transparency beats pushback

When James joined Snowflake, he faced an org-wide credibility issue. Sales didn’t necessarily trust the comp team. The plans were unpopular.

Instead of jumping to fixes, James prioritized transparency. ��

Step 1: He listened.

He went on a tour gathering raw, unfiltered feedback from frontline reps to senior leaders. Then he played it all back—literally. Every complaint surfaced verbatim. And in the next breath, he showed the updated plan and how it addressed specific issues they'd heard about.

The rollout slide deck featured a simple but powerful format: “What we heard” on the left. “How we’re fixing it” on the right.

This wasn’t just a comms exercise—it was excellent change management. The lesson? In times of change, alignment isn’t optional. It’s the cost of transformation. People will accept tradeoffs if they feel heard and understand the reasoning. How you communicate the plan changes and the benefits (and downsides!) to them is key.

On translating executive vision into seller clarity

You know the story: ELT wants the moon. Reps want clarity. Your job is to thread the needle.

Because executives speak in vision and sellers speak in comp math, Sales and RevOps sits in the middle, translating. ��

And this is where James shines as a former seller turned strategist. He underscored the importance of acting as a translator between executive ambition and sales reality. Specifically using “soft closes,” feedback loops, and clear constraint modeling, he ensures sellers understand how their effort maps to income—without watering down the strategic direction.

He doesn’t just relay orders from the top—he validates feasibility from the field, does the modeling, and aligns affordability. He treats it like a sales motion: replaying the ask, confirming understanding, and checking alignment with a soft close. The result? Plans that reflect reality—and drive the behavior execs actually want.

To apply this yourself:

• Start by aligning with your ELT: What are the top three behaviors or outcomes they want to drive? ��

• Then, model affordability with finance and identify comp levers that reinforce those behaviors. ��

• Finally, pressure-test with field leaders—validate that the plan resonates, is understandable, and drives the intended motion. ��

• When confirming alignment, borrow tactics from sales: replay the ask, and say things like, “If we shift this measure, does that solve the issue you raised?” or “If I delivered this comp structure, would that address your team’s concern?” ��

These soft-close techniques reduce surprises, surface objections early, and ensure everyone feels heard. Just like in sales, it’s not just what you pitch—it’s how you confirm buy-in that determines success. The result? Plans that reflect reality—and drive the behavior execs actually want.

Discipline scales. trust sustains.

James Jackson isn’t just building compensation plans. He’s building GTM machines that can flex with market conditions, mirror strategy, and earn the trust of every stakeholder involved. For RevOps and comp leaders navigating growth, contraction, or transformation—his playbook is required reading.

Want more insights like this? Subscribe to The Sales Compensation Show on Spotify or Apple Podcasts for bi-weekly episodes featuring the revenue leaders behind today’s fastest-growing companies.