Benjamin Encz

Ashby Culture

When the Ashby team met for the first time, we took a moment to reflect on and codify the attributes we value most in those we hire, and on the operating principles that guide our work. We'd like to share that with you here.

Ashby’s Operating Principles

Alan

Altura

aronow.io

Assured is a claims automation insurtech backed by leading Silicon Valley investors.

Assured

Astronomer

Attentive

Aurora Solar

Aven

Our camps give kids both a place to start and plenty of room to grow outdoors as they build skills in a wide range adventure sports, including mountain biking, hiking, kayaking, rock climbing and paddling.

Avid4 Adventure

Benchling

iPaaS integration platform with a worldwide reach

Boomi

Boulevard

Brightline brings virtual behavioral and mental health care to kids and teens, with a focus on also supporting families. 

Brightline

The Browser Company

Calm

Census

Character.AI

Clay

Clever

CloudTrucks

Coder is a remote infrastructure development platform that makes working with code easier than ever. Coder enables everyone from industry rookies to experts to develop code faster than ever before, using templatized starting points and ultra-secure workspaces.

Coder

Cognition Labs

Cohere

Cointracker

Color

Confluent

Convictional uses technology to make logistics easier for retailers and their suppliers by automating supplier integration, onboarding, and merchandising.

Convictional

Costanoa Ventures

Enterprise-grade accounting, audit, and tax software for your digital assets

Cryptio

Cursor

Dave

Decimal

Deel is payroll for modern business. No matter where you're hiring, Deel helps customers run payroll, supporting 150+ countries with hundreds of worldwide experts. Deel helps their customers know that hiring, paying, and managing stayed compliant and easy in their all-in-one platform.

Deel

Deepnote

Deliveroo

Docker

Dune

Duolingo

EightSleep is more than a mattress company - it's a suite of products devoted to sleep fitness. Their goal is to make sure that your sleep is as high-performing as you are, helping you meet and exceed the bar for excellence in your waking life. Athletes and scientists alike love their range of highly customizable sleep tech because it helps them live healthier.

EightSleep

ElevenLabs

An AI customer service agent for help desks.

Flock

Form Energy

Format One

FullStory is an insight platform that aims to create a more perfect web experience by capturing website data to give clients like GNC, Carvana, and Lowe’s greater insight into how users access their websites.

FullStory

Galileo

Gorgias

Granola

GrowthAssistant

HackerOne

Harvey

Help Scout

incident.io

Infinite Lambda

Ironclad

January transforms the lives of borrowers by bringing humanity to consumer finance. Their data-driven products empower financial institutions to streamline collections, providing borrowers with straightforward and compassionate solutions to regain financial stability and control over their lives. 

January

Juni

A leading developer of API and AI connectivity technologies

Kong

Kustomer

Leapsome

Lemonade

Lime

Linear

Linktree

Lovable

Machinify

Marqeta is a modern card issuing platform dedicated to empowering innovators to launch their products to the world. They have over a decade of experience as a trusted, high-tech solution for builders who need simple, scalable payment solutions.

Marqeta

Mastodon

Mercury

Metaview

Modern Treasury

Monte Carlo is a Series D data observability company helping its customers accelerate the adoption of data to eliminate downtime. 

Monte Carlo

Multiverse

NETGEAR

Notion is the go-to for notes, tasks, wikis, and databases, blending everyday work apps into one. It serves as an all-in-one workspace for note-taking, task management, and project management. 

Notion

Compensation software that offers 5,000+ companies clarity for every pay decision.

OpenComp

Opendoor

Oyster HR

Plaid

Plato

PostHog

PostHog is an open source analytics platform. Their product is used by product, engineering, and marketing teams to understand user behavior, including product analytics, session recording, user paths, a/b testing, heatmaps, and more. The suite, founded through Y Combinator in 2020, has since been installed by over 10,000 companies.

Pragma Platform

ProAmpac

Pulley

QFinds

Quora

Rad AI

Ramp

Readme

Recruiting Pundit

Reddit

Replit

Resend

Retool

peer network for senior in-house resourcing leaders

RL100

Scratchpad

With over 2k clients and 20+ years of experience, Sequoia Consulting Group  is a services, tech, advisory business that provides clients with a platform for rich analytics.

Sequoia

Engineering Updates

Recruiting Articles

Mike Clapson

The average salesperson hears “HR Tech” and imagines slow-moving buyers, small budgets, and software that is functional but boring. That's the myth. 

Thankfully, the reality is much more interesting: 

HR tech is a massive, fragmented, increasingly technical market being reshaped by AI

. For the right salesperson, it is one of the most compelling enterprise software opportunities of the next decade for a number of reasons:

Every company has employees. Nearly every company hires. And as they grow, they need systems to recruit, schedule, assess, onboard, pay, develop, and retain those employees.

That creates a market with unusual breadth. HR software is not a niche product category serving a narrow set of specialists; it sits underneath one of the most important operating processes in every business: building the team.

Market estimates vary depending on what is included, but 

 puts the global HR technology market at more than $40 billion today, growing toward more than $85 billion over the next several years.

Fragmentation creates room for a full-suite winner

The overall HR, talent, and people market is also remarkably fragmented. Many companies run recruiting on an ATS, sourcing in another tool, scheduling somewhere else, analytics in spreadsheets, and AI workflows across a growing collection of point solutions. Around those products sits an even larger services ecosystem helping customers configure, integrate, and operate the stack.

Fragmentation creates pain, but it also creates leverage. A platform that can consolidate several products can create more value than any point solution. Customers get fewer vendors, less context switching, better data, and workflows that actually connect end to end. In return, the platform provider earns a much stickier, stronger relationship and the ability to expand and scale with their customers.

That is the opportunity behind Ashby’s full-suite approach. We are not trying to win one isolated feature at a time. We are building a platform for how modern companies hire — and then expand into adjacent parts of the employee lifecycle, like 

 for onboarding, and beyond. We’ve seen this proven scaling strategy deployed with great success in other SaaS verticals. 

The category already produces enormous companies

This is not a market where the upside is theoretical. Rippling, founded in 2016, reached a private valuation of $16.8 billion in 2025. Deel, founded in 2018, reached a $17.3 billion valuation that same year. Both companies were launched within the last decade, and both built businesses by solving important, complex problems for employers.

Even more recently, Silver Lake was reported to be in talks to take Workday private in a transaction that could exceed $50 billion. If completed, it would rank among the largest software buyouts in history. The fact that a major private-equity firm is considering that size of check for an HR and Financials company is itself a powerful signal about the value and durability of deeply embedded systems of record, even in an AI era. HR Tech can produce companies at the very top end of enterprise software.

AI expands the opportunity beyond software budgets

Historically, recruiting and HR processes relied heavily on human work. Recruiters manually sourced candidates, coordinated interviews, sent follow-ups, screened applications, assembled reports, and moved information between disconnected systems.

Software mostly helped people organize that work. But, AI changes the equation. The opportunity is no longer just to make a recruiter 10% more efficient; it is to let software perform meaningful parts of the end-to-end workflow itself. 

 takes screening calls for high volume roles, saving organizations on headcount while improving recruiting outcomes.

 argues that HR is one of the last large enterprise categories without a serious AI-native challenger. The next generation of HR systems can be built around agents, open data, permissions, and workflows — not forms and approvals. That is not just a product opportunity; it is a market-reset opportunity. Workday’s installed base proves how much value is concentrated in the system of record, while the limitations of legacy architecture show how much room there is for a better one.

When software replaces labor, it unlocks budgets that historically went to headcount, agencies, and outsourced services — not just the relatively small software line item. The biggest opportunities will come from platforms that combine a system of record with automation and intelligence.

“Less sexy” can be a competitive advantage

There is another second-order benefit: fewer ambitious companies and founders are attacking HR tech than are attacking categories like developer tools, fintech, or consumer AI.

That does not mean the market is easy to move. But, the bar is somewhat lower for a great company to stand out. A product that is genuinely better, faster, more thoughtful, and more loved by customers can build meaningful separation in a category where many incumbents have been protected by inertia.

In other words, the lack of glamour is not necessarily a weakness. It may be a systemic source of underinvestment — and therefore opportunity.

The buyers are better than the stereotype

HR leaders are sometimes described as indecisive buyers with limited budgets. That has not been my experience.

People and Talent leaders tend to be transparent, engaging, thoughtful, and highly motivated by outcomes. They care deeply about the quality of the process and the experience of the people moving through it. They are often more collaborative (and more fun to work with) than the stereotypical IT or Engineering buyer.

The best HR tech conversations are not about an administrative tool and recruiting efficiency. They are about helping a leadership team win the best talent, drive revenue and product velocity, and ultimately build a stronger, more competitive company.

Finally, don't confuse a friendly buyer with a simple sale.

A modern ATS is at least as complex as a CRM, ERP or ITSM platform. It manages workflows, permissions, integrations, analytics, communications, scheduling, data quality, compliance, and increasingly AI-powered automation. It touches recruiters, hiring managers, executives, Finance, IT, Legal, and candidates. It becomes a mission-critical system of record.

Selling it requires discovery, technical fluency, business acumen, project management, and the ability to build consensus across a complex buying group.

If you want to sell something that everyone already agrees is exciting, HR tech may not be for you.

second-order thinking, complex products, large markets, kind and ambitious buyers, and the chance to help define a category before it is fully formed

, HR tech is a remarkable place to build a career.

The market is enormous, fragmented, technically deep, increasingly powered by AI, and still early in its transformation.

That makes it an attractive market to sell into, and an ideal market in which to build a generational company.

HR Tech

HR tech is a huge, fragmented, and technically complex market that AI is reshaping, which makes it an underrated and exciting place for salespeople to build a career. Mike Clapson, VP of Sales, explains why. 

HR Tech: One of the Great Opportunities in Software Today

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.

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:

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.

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.

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 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 

 (how many months to reach full productivity) and ramp 

 (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 

 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.

Ashby designs sales quotas to be challenging but achievable, aiming for roughly two-thirds of AEs at or above quota, and re-evaluates them every quarter — adjusting down as well as up. Mike Clapson, VP of Sales, on how the plan is built and why.

Ashby Culture

Featured

Ashby’s Operating Principles

HR Tech: One of the Great Opportunities in Software Today

How We Think About Sales Quotas and Incentives at Ashby

Bringing Talent Llama's AI Interviewer into Ashby

A Letter from the Talent Llama Co-Founders on Joining Ashby

The Next Phase of Ashby: Key Announcements from Ashby One

Product

Resources

Company

Developers

Ashby Culture

Featured

Ashby’s Operating Principles

HR Tech: One of the Great Opportunities in Software Today

How We Think About Sales Quotas and Incentives at Ashby

Bringing Talent Llama's AI Interviewer into Ashby

A Letter from the Talent Llama Co-Founders on Joining Ashby

The Next Phase of Ashby: Key Announcements from Ashby One

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