How We Think About Sales Quotas and Incentives at Ashby

If you work in sales long enough, you learn that the compensation plan tells you a lot about how a company operates.

At some companies, quotas feel arbitrary. They get handed out as an exercise in aspiration, not as realistic targets. When that happens, reps don't just lose confidence in their ability to earn, but they also lose trust in the business. And once trust erodes, it becomes much harder to build the kind of momentum that a world-class sales team needs.

We think about sales incentive comp differently at Ashby.

We have put a meaningful amount of thought into how quotas are designed, how incentives work, and how compensation evolves over time. The goal isn’t to create a model that looks good in a spreadsheet to the finance team; instead, it's to create a system that is fair, data-driven, motivating, and durable.

That matters for take-home pay, of course. But it also matters for something even more important: the feeling that if you do the right work, the right way, success compounds. Early wins build confidence. Confidence improves execution. Better execution creates more wins. We want our quotas and incentives to reinforce that flywheel.

The company behind the plan

None of this matters if the company flames out before you finish ramp, so it's worth starting with how deliberately Ashby has been built. We've grown efficiently, scaling revenue far faster than we've added people:

• Roughly 15x revenue growth on only ~6x headcount growth over the last 3 years.

• Exceeded our aggressive revenue plan for 12+ consecutive quarters.

• Held roughly two-thirds of AEs at or above quota while doubling the sales team year over year.

That track record of intentional, sustainable growth is what makes everything below credible. A quota system is only as trustworthy as the business it supports.

We design quotas to be "challenging, but achievable"

Those words sit at the top of our Sales Compensation Philosophy document.

Our aim is for roughly two-thirds of AEs to be at or above quota, and Ashby has a multi-year track record of staying close to that goal. Most companies will never tell you what they actually model their quotas around — I'd encourage you to ask. The truth is that most companies expect ~35–45% of AEs to hit quota. They factor that into their productivity assumptions and build even bigger sales teams to account for the expected level of failure. They hide this with high OTEs and invite you to talk to a top-performing rep during the interview cycle. We think this model is broken.

Quotas that are too high can create burnout, turnover, and a sense that the plan is disconnected from reality. Of course quotas can't be too low either, because the business needs the sales team's revenue contribution (less commissions) to fund the rest of the company's growth and headcount. Ashby's goal is to balance both sides of that equation so that strong performers are very well paid while the company preserves sustainable sales efficiency.

One of the most important ways we hold ourselves to that standard is a quarterly quota evaluation process.

We revisit quotas quarterly

Most companies set quotas once at the start of the year and leave them static. When reality shifts, those static targets are exactly what create the burnout and broken trust described above.

We do it differently. Revenue Operations, Sales Leadership, and Finance collaborate every quarter to evaluate and, where warranted, adjust quotas. This is an intentional decision. It holds us accountable, and it gives us the flexibility to keep targets fair as a fast-scaling business changes around them. Quotas are not "set and forget."

More frequent assessment of quotas creates more operational work, but this lets us respond to reality — team growth, territory changes, shifting market conditions, and evolving productivity patterns. In practice, quotas move up or down by team or region when the data says they should. The result is not wild swings; it's appropriate adjustments that keep quotas current, credible, and fair.

Unlike most companies, where "quotas only go up," we have a track record of reducing quotas where appropriate — especially when we successfully hire a group of strong reps into a given team or segment. Our hiring is sustainable not only because of our strong product-market fit and large addressable market, but also because we add great AEs to already successful teams, where existing reps share what's working and help everyone succeed. That combination has helped us keep AE attrition low over the last 3+ years, even as the team grows.

We'd rather refine the system than pretend the original assumptions can never change.

We use data, not wishful thinking

A lot of sales orgs talk about being data-driven. Few actually anchor quota-setting in past performance and real operating conditions.

At Ashby, quotas are set using multiple data sources, including historical sales performance, top-down finance objectives, productivity assumptions, demand flowing into a region, seat capacity, and multiples on total sales compensation. Just as importantly, there is no single input that dominates the process; those signals are used together to narrow in on fair targets by region and segment.

We are not setting quotas based only on what we hope productivity could become. We look hard at what the business has historically produced, what current market conditions support, and what changes are likely to help or hinder attainment.

Ramp is designed thoughtfully by segment

Ramp is another area where our philosophy shows. We use segment-specific ramp periods because different segments have different sales cycles, complexity, and time-to-productivity. The right ramp for a shorter-cycle segment is not the right ramp for Enterprise; fairness is not sameness.

We also put real analytical rigor into the ramp itself. We run a separate evaluation process that goes deep on both ramp timeline (how many months to reach full productivity) and ramp shape (for example, a slower build across the first few months followed by a sharper increase). And because we're scaling quickly — roughly doubling headcount year over year — we compare ramp cohorts over time (this year versus last) to account for a changing selling landscape.

Just as importantly, our ramp philosophy is designed to give new reps a viable path to earning OTE while onboarding. Ramp is explicitly not a draw. New reps are not simply being advanced earnings they'll later have to claw back through future commissions.

Instead, ramp quotas, pay rates, and attainment mechanics are structured to help reps build confidence and momentum early. New reps should have a path to both quota attainment and OTE during ramp, with uncapped commissions and consistent treatment for over-attainment.

Early months shape belief. A thoughtful ramp helps a new rep focus on learning, building pipeline, and winning the right way, rather than feeling buried by a fully loaded target before they've had a fair chance to succeed.

Our Enterprise Guarantee reduces friction, not upside

Enterprise selling is hard. Longer cycles, more complexity, and higher expectations mean a one-size-fits-all compensation approach breaks down quickly.

That's why Ashby pairs the Enterprise ramp with a Commission Guarantee. It's a step-functioned guarantee that provides a base level of variable earnings during ramp while still allowing the rep to earn OTE. More importantly, Enterprise reps receive the guarantee and are paid on deals they close during ramp — preserving real upside instead of forcing a tradeoff between security and earnings potential.

These details make a huge difference when you're a senior rep considering leaving somewhere you have a proven track record and active deals in your pipeline.

We want incentives to reinforce the right behaviors

Thoughtful quota design is only part of the picture. Additional incentives matter too.

Ashby's commissions and incentives are designed to reward ARR outcomes while avoiding mechanics that create misalignment. Based on sales team feedback in 2025, we now offer two tiers of accelerators, with the top tier paying AEs double their base commission rate above 150% attainment. We want to ensure that top performers are materially rewarded.

We also reward contributions that drive impact over the long term. One example is our Sales Outbound Lifetime Achievement Award, which recognizes cumulative self-sourced outbound closed-won revenue over a rep's career at Ashby, with milestone-based cash awards and public recognition. It celebrates long-term outbound excellence, not short-term quota performance. Cash awards start at $2,500 and go all the way up to $50,000 for achievements we expect to see over a period of several years.

The bigger picture

A good quota and incentives system should do a few things at once: establish a fair and transparent compensation system, ensure high performers earn very well, and create a sense that consistently high-quality work creates meaningful success. When sellers trust the plan and believe the targets are grounded in reality, they can spend more of their energy on the work itself — and that's the outcome we care about most.

We’re building a thoughtful, high-performing Sales organization at Ashby. See our open roles to consider joining.