Hi! I’m Rachel and I lead People Operations here at Ashby. I recently joined and I’m excited that we're expanding our team! The People Operations Team provides support to Ashby employees through the development and implementation of programs, policies, and services that contribute to a productive and inclusive working environment. We ensure that the work we do aligns with our Operating Principles and strengthens the environment we're building at Ashby. Our approach is to do things differently – we prioritize what truly fits our team and enhances how we work together. By embracing creativity and customization, we aim to create a people-first culture that drives both individual and organizational success.

We review all applications, and there isn’t a benefit to applying quickly. Take your time, look at the application questions and please submit before the application deadline! We aren’t able to take calls outside of the interview process, so reaching out to the team won’t push your application forward.

About the Role

We’re looking for an experienced Total Rewards leader to build and own Ashby’s total rewards function through our next phase of growth.

This is a builder’s role. Some of the foundation is in place; a lot of it isn’t. You’ll set the philosophy, design the frameworks, build the infrastructure, and run the work day to day. It’s a chance to shape how a company rewards its people rather than administer decisions someone else made.

It’s also unusually analytical, and unusually creative. Ashby’s Total Rewards philosophy is principled and intentionally not one-size-fits-all: approaches vary by function, because different parts of the business compete in different talent markets. Total Rewards partners closely with leadership to provide the structure, documentation, guidance, and governance that keep those approaches equitable, competitive, and scalable. The upshot is that the most interesting problems here don’t have off-the-shelf answers. How do you price a role that survey data doesn’t cover? How do you keep a flexible system fair and explainable? How do you tell, early, that one talent market has moved while the others haven’t? You’ll need real fluency with data, the discipline to structure a problem before you solve it, and the confidence to invent the model when no model exists.

A lot of this work looks less like administering a program and more like a well-run strategy engagement: frame the question, get the data, build the model, pressure-test the answer, and bring leaders a recommendation with the tradeoffs made explicit. The difference is that here you also go implement it.

You’ll partner closely with People Ops, Finance, Talent Acquisition, Legal, and functional leaders to design programs that support how Ashby attracts, retains, and rewards exceptional people — building a more scalable approach while preserving the flexibility each part of the business needs.

We’re looking for someone who has built and scaled Total Rewards in high-growth, VC-backed SaaS companies and is energized by all three of philosophy, systems, and execution — someone who would rather go build the analysis than wait for it.

This role starts as an individual contributor and is expected to grow into people management as the function scales.

You'll be responsible for

Building Ashby’s compensation infrastructure

Bands, leveling alignment, market positioning, review cadences, benchmarking methodology, and clear guidance for offers, promotions, refreshers, and market adjustments — globally, and in partnership with founders, executives, and functional leaders. Some areas are mature; others are still forming. You’ll bring structure to the ambiguity with frameworks that are principled, practical, and hold up under scrutiny. You will be responsible for helping leaders reason through tradeoffs, bringing them a clear recommendation and the logic behind it, and documenting the non-standard rather than handing anyone a rule book.

Reading the market and helping Ashby adapt quickly

Combine market data, internal data, and outside signals to allow us to respond quickly and at scale when conditions change. Build the mechanisms that catch market movement across the whole company, not just the functions with the loudest signals: find the gaps in survey coverage, spot which teams are repricing faster than others, form a view on why, and turn what you see into a recommendation.

Owning Total Rewards strategy end-to-end

Compensation, equity, benefits, and perks. With founders and company leaders, define the philosophy, principles, and long-term direction for how we reward people globally. Evaluate our programs continuously and make recommendations that balance market competitiveness, internal equity, business needs, and long-term sustainability — framed the way a good strategy memo is framed: the options, the tradeoffs, and where you land.

Leading benefits strategy and administration

Own global benefits end to end: strategy, selection, renewals, plan design, competitiveness assessment, broker and vendor management, and the systems and processes behind a strong employee experience.

Leading equity program infrastructure

Partner with Finance and company leadership to bring structure, consistency, and scalability to equity practices, support program administration, and help employees understand how equity fits within the broader Total Rewards picture.

Building scalable systems and operations

Improve the systems, workflows, documentation, and operational processes behind Total Rewards. You will work in tools like CandorIQ, Pave, and OpenComp. You will use automation, AI, and good operational design to get roles to market quickly, support pay decisions efficiently, and keep the underlying data trustworthy.

Acting as a trusted cross-functional partner

You’re the subject matter expert for Total Rewards at Ashby. You’ll help leaders navigate rewards decisions with sound judgment, fairness, and clarity — and make complicated questions land simply in front of founders and executives.

Preparing the function to scale

You begin as a hands-on functional owner, but you’ll build with future scale in mind by establishing the documentation, operating rhythms, standards, and decision-making frameworks the function will need as it grows, and flagging the organizational needs ahead.

You could be a great fit if

• You bring several years of progressive Total Rewards experience, including meaningful ownership of compensation, benefits, and equity programs in high-growth organizations and you’ve built compensation infrastructure from the ground up.

• You bring an analytical first mindset. You build the model, pressure-test your own numbers, and would rather run the analysis yourself than wait for someone else to.

• You’re a structured thinker. You take a messy question, break it into the parts that matter, form a hypothesis, and test it — and you can walk someone through your reasoning without losing them.

• You’re a creative problem solver in the comp space. When benchmarks are thin or the role is new, you reason from first principles and design the approach that fits the problem and not the one you used last time.

• You’re comfortable where some principles are centralized and other elements are tailored by function, and you can keep that flexibility equitable and explainable.

• You’ve built and scaled compensation frameworks and benefits programs for globally distributed organizations, ideally through periods of significant growth.

• You can support leaders with different needs and viewpoints while holding the line on trust, consistency, and decision quality.

• You’re highly effective at both strategy and execution, and comfortable being the primary owner of the work day to day.

• You’re an exceptional communicator who can make complex Total Rewards topics land with any audience and can show the reasoning behind a number, not just the number. You’re comfortable putting a recommendation in front of founders and defending it.

• You’re detail-oriented and operationally strong, always looking for ways to improve systems, processes, and program quality.

• You’ve led or managed others, or you’re excited to build and eventually scale a Total Rewards team.

Bonus points if you have

• Experience building and scaling global compensation and benefits programs across multiple regions and employment models.

• Experience using automation, AI, and technology to make Total Rewards operations faster, more accurate, and more scalable.

• Strong modeling and data skills beyond the standard toolkit including advanced spreadsheet work, SQL, Python, or BI tools.

• A background that blends Total Rewards with strategy consulting, corporate finance or FP&A, or people analytics. We value people who have been trained to structure and solve ambiguous problems, wherever they learned to do it.

• Experience with tools such as CandorIQ, Pave, and OpenComp.

This role may not be a fit if

• You want to bring your own Total Rewards playbook and install it at Ashby, rather than reimagine and evolve what’s already been started.

• You prefer operating inside highly standardized programs to building and adapting them in a more flexible environment.

• You’re less interested in the hands-on work of running the function — including doing the analysis yourself.

• You reach for the benchmark before the reasoning, or you need rigid rules to make a call.

• You’d rather present the data than the recommendation.

• You’re uncomfortable making decisions in ambiguity or helping leaders through nuanced compensation questions.

• Your experience is concentrated in one area of Total Rewards, with limited exposure across compensation, equity, and benefits.

• You’re not energized by partnering across functions, balancing competing perspectives, and shaping practical solutions.

• Most of your experience is in mature organizations with established programs, processes, and teams, without having had to build infrastructure through growth and change.

Interview Process

Our interview process is thorough — we aim to ensure each person joining the team is the right fit for Ashby and will provide ample information to assess if Ashby is the right fit for you. The process for this role is as follows:

• Recruiter Screen with Talent Acquisition Team - 30 minutes

• Hiring Manager Interview - 45 minutes

• Take Home Assignment

  • Followed by 1 hour live session to discuss

• Virtual Onsite - 2.5-3 hours

• Final Round with CEO - 30 minutes

About Ashby

We’re building the next generation of recruiting software and we’re starting with a suite of products that helps talent leaders, recruiters, and hiring managers run an efficient and data-driven hiring process. We are well funded and backed by great investors, including Y Combinator, Elad Gil and Lachy Groom. We have thousands of amazing customers including Snowflake, OpenAI, Shopify, Ramp, Notion, and Zapier (and many others who we cannot name!). Our growth and retention metrics are best-in-class among our peers: we have tens of millions in ARR, growing >100% year over year, very low churn, and many years of runway. We’ll share more details once we meet. In short, it's the perfect time to join! 🚀

Benefits

• Competitive salary and equity.

• 10-year exercise window for stock options. You shouldn’t feel pressure to purchase stock options if you leave Ashby —do it when you feel financially comfortable.

• Unlimited PTO with four weeks recommended per year. Expect “Vacation?” in our one-on-one agenda until you start taking it 😅.

• Twelve weeks of fully paid family leave in the US. We plan to expand this to employees in other countries as situations arise.

• Generous equipment, software, and office furniture budget. Get what you need to be happy and productive!

• $100/month education budget with more expensive items (like conferences) covered with manager approval.

• If you’re in the US, top-notch health insurance for you and your dependents with all premiums covered by us.

Ashby’s success hinges on hiring great people and creating an environment where we can be happy, feel challenged, and do our best work. We’re being deliberate about building that environment from the ground up. I hope that excites you enough to apply.

Ashby provides equal employment opportunities (EEO) to all employees and applicants for employment without regard to race, color, religion, sex, national origin, age, disability, genetics, sexual orientation, gender identity, or gender expression. We are committed to a diverse and inclusive workforce and welcome people from all backgrounds, experiences, perspectives, and abilities.

Ashby is committed to a fair and transparent hiring process. We confirm that this advertisement is for an active, existing vacancy within our organization. Please be advised that we may use artificial intelligence-driven tools to assist our recruitment team in screening, assessing, and selecting candidates for this position.