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 both a strategic and hands-on role responsible for how we approach compensation, equity, and benefits globally. You’ll serve as the functional owner for Total Rewards responsible for setting the philosophy, building the infrastructure, and driving execution while bringing the judgment and leadership needed to help us scale the function over time.
Ashby’s Total Rewards philosophy is thoughtful, principled, and intentionally not one-size-fits-all. Compensation approaches may vary by functional area in order to best fit each part of the organization. Total Rewards provides the structure, documentation, guidance, and governance needed to ensure those approaches remain equitable, competitive, and scalable. Across the company, our shared intent is to be competitive in the market and adapt quickly as markets evolve.
In this role, 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 talent. You’ll help us build a more scalable approach to compensation and total rewards while preserving the flexibility that allows different parts of the business to operate effectively.
We’re looking for someone who has built and scaled Total Rewards programs in high-growth VC backed SaaS companies and who is equally energized by philosophy, systems, and execution. You should be comfortable defining direction while also rolling up your sleeves to run analyses, refine tools and processes, support leaders through nuanced decisions, and build the operating foundation for the future.
This role will start as an individual contributor and is expected to evolve into people management as the function scales.
You'll be responsible for
Building Ashby’s compensation infrastructure
You’ll work closely with founders, executives, and functional leaders to build and evolve Ashby’s compensation foundations globally. This includes compensation bands, leveling alignment, market positioning, review cadences, benchmarking methodology, guidance for offers, promotions, refreshers, and market adjustments, and clearer compensation structure where it is still needed.
You’ll help ensure our approach can support a mix of more mature compensation structures and areas where it is still evolving. You’ll bring structure to ambiguity and create frameworks that are principled, practical, and scalable. You will support leaders in assessing tradeoffs, documenting non-standardized components, and put the right level of governance in place.
Monitoring the market and helping Ashby adapt quickly
You’ll leverage market data, internal data, and external trends to inform compensation decisions across the business. You’ll help Ashby maintain its target market position and ensure we are responding thoughtfully and consistently when market conditions change.
This includes identifying where certain teams may be moving faster than others, spotting gaps in coverage, and building mechanisms to ensure we are catching market movement across the company, not just in the functions with the loudest signals.
Owning Total Rewards strategy end-to-end
You’ll own Ashby’s Total Rewards strategy across compensation, equity, benefits, and perks. In partnership with founders and company leaders, you’ll define the philosophy, principles, and long-term direction for how we reward employees globally.
You’ll continuously evaluate our programs, identify opportunities to improve them, and make recommendations that balance market competitiveness, internal equity, business needs, and long-term sustainability.
Leading benefits strategy and administration
You’ll lead the strategy, selection, evaluation, and ongoing management of Ashby’s benefits programs globally. This includes broker and vendor management, renewals, plan design review, competitiveness assessment, and the systems and processes that support a strong employee experience.
Leading equity program infrastructure
You’ll help operationalize Ashby’s equity programs in close partnership with Finance and company leadership. You’ll bring greater structure, consistency, and scalability to equity practices, support program administration, and help employees better understand how equity fits within our broader Total Rewards philosophy.
Building scalable systems and operations
You’ll continuously improve the systems, workflows, documentation, and operational processes that support Total Rewards. You’ll work with tools such as CandorIQ, Pave, and OpenComp to help Ashby get roles to market quickly, make pay decisions efficiently, and adjust programs as the business and market evolve.
You’ll look for opportunities to use automation, AI, and strong operational design to improve efficiency, increase accuracy, and create a better experience for employees, managers, and the People team.
Acting as a trusted cross-functional partner
You’ll serve as the subject matter expert for Total Rewards across the organization. You’ll partner with Finance on budgeting and workforce planning, Talent Acquisition on hiring strategy and offer guidance, and People Business Partners and functional leaders on promotions, organizational changes, and complex compensation decisions.
You’ll help leaders navigate rewards decisions with sound judgment, fairness, and clarity.
Preparing the function to scale
While this role begins as a hands-on functional owner, you’ll build with future scale in mind. You’ll establish the documentation, operating rhythms, standards, and decision-making frameworks needed for the function to grow over time, and you’ll help identify future organizational needs as Ashby continues to scale.
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.
You have deep compensation expertise and have built compensation programs and infrastructure from the ground up.
You understand how to operate in an environment where some principles are centralized and other elements are tailored by function.
You’re comfortable navigating ambiguity and using data, judgment, and business context to make recommendations.
You’ve built and scaled compensation frameworks and benefits programs for globally distributed organizations, ideally through periods of significant growth.
You know how to support leaders with different needs and viewpoints while maintaining trust, consistency, and strong decision quality.
You’re highly effective in both strategy and execution and are comfortable being the primary owner of the work day to day.
You’re an exceptional communicator who can explain complex Total Rewards topics clearly to a wide range of audiences.
You are detail-oriented, operationally strong, and always looking for ways to improve systems, processes, and program quality.
You’ve previously led or managed others, or you’re excited to help build and eventually scale a future Total Rewards team.
Bonus points if you have
Experience building and scaling global compensation and benefits programs across multiple regions and employment models.
Experience leveraging automation, AI, and technology to improve the efficiency, accuracy, and scalability of Total Rewards operations.
Experience working with tools such as CandorIQ, Pave, and OpenComp.
An advanced degree in HR, business, finance, or organizational development.
An HR certification such as PHR, SPHR, SHRM-CP, SHRM-SCP, CCP, or CEBS.
This role may not be a fit if
You want to bring your own total rewards play book and implement it at Ashby rather than reimagining how to evolve what has already been started.
You prefer operating within highly standardized Total Rewards programs rather than building and evolving them in a more flexible environment.
You are less interested in the hands-on work required to run a Total Rewards function.
You’re uncomfortable making decisions in ambiguity or helping leaders navigate nuanced compensation questions without overly relying on rigid rules.
Your experience is concentrated in only one area of Total Rewards, with limited exposure to compensation, equity, and benefits more broadly.
You’re not energized by partnering across functions, balancing competing perspectives, and shaping practical solutions.
Most of your experience has been in highly mature organizations with established programs, processes, and teams, and you haven’t had to build infrastructure during periods of 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.
