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Head of HR Operations and Systems

Ashby · Remote - US · 2026-06-09

FullTimeexecutiveRemote
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About this role

Head of HR Operations and Systems

Overview
You’re a great Human Resources Operations and Systems Leader who is so passionate about the day to day work of HR Operations that you’re willing to join an early stage company to build out the HR Ops function by doing all the dirty work yourself for a long period of time. You’re likely especially willing because this role gets you behind the curtain of HR technology, enabling you to geek out at the intersection of People technology, process and data. You care so deeply about operational excellence, company efficiency and system enabled employee experience, that it makes you outspoken compared to the majority of HR Ops professionals and you would relish constantly experimenting with better ways to do HR Operations. This role will initially have one report, our recruiting operations lead.

About the Role
Hi 👋🏼 I'm Jim https://www.linkedin.com/in/jmmmmmmmmmmmmmmmmmmmm/, the VP of People and Talent at Ashby. I’ve been lucky enough in my career to have been in roles that change the landscape of TA technology we use every day, been exposed to massive hiring data sets and been tasked with reimagining TA processes across a wide range of company scales. I joined Ashby to continue this work and to be a disruptor in how companies hire and support great people.

I’m looking for a thought partner on the HR Operations and Systems side of our People function and we’re at the scale now that will support that role. To be clear, this role is in our internal People team, not a customer facing role in our Professional Services team, however, I expect you will still end up speaking to customers and prospective customers!

This role will be the foundation of how we scale the next iterations of Ashby as a company. You will be expected to review all our existing People practices and drive the right change for what we need now, what we will be and beyond. That change will include low level polish (think template editing and creation) to process change, systems implementation, data analytics, and of course, documentation https://www.ashbyhq.com/blog/culture/thoughtful-communication. You’ll be an expert at communicating change too, able to influence change across the company while driving innovation in our tech stack and processes.

This role will evolve based on the growth of Ashby, so comfort with ambiguity is important. This is not your run of the mill HR Ops role, instead you’ll become an expert on our world class people technology suite, be the internal change agent I described above and an external thought leader. You will be called upon to chat with customers, with Product Managers, to talk at conferences and to write compelling content for an audience of People professionals and Hiring Managers.

Why you should or shouldn’t apply

HR Operations encompasses many different types of work. Not all of which you’ll ever do in this role. The following list will help you decide if this role is for you

- You’re first-hand experienced with our product and excited by the power it offers Talent Acquisition teams and are intrigued by where else in the People tech stack we might take the company. You don’t have to have had Ashby experience, but it will help.

- You love exceptional process, technology and people

- You have excellent communication skills – we value clear and concise communication

- You understand myriad stakeholders and their motivations (what matters to a Head of Department may be distinct from what matters to an individual contributor; you can help each achieve their goals)

- You’re willing to drive solutions from the simple (e.g. help solve an onboarding issue) to the complex (e.g. integration of disparate systems)

- You are have high standards and are comfortable holding others accountable and setting clear expectations, especially relevant as it pertains to securing alignment across stakeholders

- You have a high level of empathy for our employees – their pain is our pain

- You can deliver feedback in a way that keeps internal teams focused on the customer experience (in turn shaping our product roadmap) for you are also a customer

- You are excited to shape our HR Operations and systems team as the first leader and by this point in this JD your brain already has a vision of what you’ll do

You might not be a great fit if:

- You prefer defined structure and are not excited by ambiguity or amorphous opportunities

- You prefer to spend your time focused on one or two priorities and are not comfortable context switching across several focus areas

- You are uneasy holding customers accountable or otherwise serving as arbitrator when competing opinions are presented

- You have difficulty setting boundaries and tend to default to a ‘yes’ stance

- You are not interested in a supporting role where you take on less interesting or visible work alongside the really fun stuff

- You haven’t led an experienced team before

You need a team to do the work. This is, and will be for quite some time, a small but experienced team of ~2.

Examples of things you’ll work on:

- Systems

- Managing all HR Systems. Defining what we require and why, externally and internally, for our unique People tech stack.

- Reporting

- Building a full suite of reports and dashboards that use Ashby’s analytical capability to the maximum as well as that of other tools

- Process Improvement

- Continuous improvement is critical and we want to challenge the status quo, not just for ourselves but to experiment publicly with what’s possible.

- Performance Management

- Create and operationalize performance review processes and develop frameworks for evaluating and growing talent.

- New Initiatives:

- Lead employee engagement initiatives such as surveys, build out our knowledge base, learning & development programs, and other people-focused programs.

- Partnering closely with the Product Team to distill your observations into…

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