Sr. Total Rewards Manager - Ashby

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 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. 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.

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.

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

Responsibilities

• 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.
• Reading the market and adapting quickly: Combine market data, internal data, and outside signals to respond quickly and at scale when conditions change across all functions.
• Owning Total Rewards strategy end-to-end: Define compensation, equity, benefits, and perks philosophy and long-term direction with company leaders while balancing internal equity, business needs, and long-term sustainability.
• Leading benefits strategy and administration: Own global benefits end to end: strategy, selection, renewals, plan design, broker/vendor management, and administrative processes.
• Leading equity program infrastructure: Partner with Finance and company leadership to bring structure, consistency, and scalability to equity practices and employee understanding.
• Building scalable systems and operations: Improve systems, workflows, documentation, and operational processes using tools like CandorIQ, Pave, and OpenComp.
• Acting as a trusted cross-functional partner: Serve as the subject matter expert helping leaders navigate rewards decisions with sound judgment, fairness, and clarity.
• Preparing the function to scale: Establish documentation, operating rhythms, standards, and decision-making frameworks for future growth.

Requirements

• Several years of progressive Total Rewards experience, including ownership of compensation, benefits, and equity programs in high-growth, VC-backed SaaS organizations.
• Experience building compensation infrastructure from the ground up for globally distributed teams.
• Analytical-first mindset with strong data modeling and problem-structuring skills.
• Creative approach to compensation in fast-moving talent markets where rigid benchmarks don't always apply.
• Comfortable balancing centralized principles with function-tailored compensation approaches.
• Excellent communication skills capable of framing complex recommendations clearly for executive leadership and founders.
• Hands-on approach and comfort serving as the primary owner and execution driver of the day-to-day work.

Nice to Have

• Experience building and scaling global comp/benefits across multiple regions and employment models.
• Experience using automation, AI, and modern HR tech tools (e.g., CandorIQ, Pave, OpenComp).
• Strong modeling skills (advanced spreadsheets, SQL, Python, or BI tools).
• Background combining Total Rewards with strategy consulting, corporate finance/FP&A, or people analytics.

Interview Process

• Recruiter Screen with Talent Acquisition Team (30 minutes)
• Hiring Manager Interview (45 minutes)
• Take Home Assignment (followed by 1 hour live discussion)
• Virtual Onsite (2.5 - 3 hours)
• Final Round with CEO (30 minutes)

Benefits

• Competitive salary and equity with a 10-year exercise window for stock options.
• Unlimited PTO (4 weeks recommended per year).
• 12 weeks of fully paid family leave in the US.
• Generous equipment, software, and office furniture budget.
• $100/month education budget.