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, 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. 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 tangible feedback. To help scale your efforts, we'll aim to resolve pain points and increase your influence with documentation; you'll be able to contribute on both of these fronts as the Voice of the Customer with a pedagogical slant
You’ll be involved in early deployment and testing of features whilst ensuring all new functionality is effectively utilized internally after release
Compliance
Ensure HR policies and practices comply with all federal, state, and local regulations. Maintain accurate employee records and documentation. Support audits and reporting requirements, and help develop training and communication to keep the organization aligned with legal and regulatory standards.
Operational Efficiency
Automation, AI deployment and efficient processes are critical to how we will scale Ashby. Your role will be to help ensure maximum impact of potential efficiency gains
Hiring Manager interview with Jim - 45 minutes
Meet a Founder - 30 minutes with Benji
Take Home Assignment and Presentation with Jim and Benji
Final Panel:
Sales Leader Interview with Mike - 30 minutes
Finance and Data Interview with Shane and Kevin - 30 minutes
Technical interview - with Abhik 30 minutes
Leadership Interview with Kelsey - 30 minutes
Your Recruiter
Your Recruiter will be me! I will be your main point of contact and I’ll help prepare you for interviews.
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 over 4,000 amazing customers including Ramp, Notion, and Zapier – yet we've only taken the first steps toward a much larger opportunity. 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.
Skills Required
- Proven experience leading an experienced HR or HR Ops team
- Hands-on experience managing HR systems (HRIS/ATS) and defining system requirements
- Experience building reports and dashboards using HR analytics tools and datasets
- Strong process improvement experience and change management skills
- Experience designing and operationalizing performance management and review processes
- Knowledge of federal, state, and local HR compliance and recordkeeping
- Excellent written and verbal communication and stakeholder influencing skills
- Experience partnering with Product teams and translating operational observations into product feedback
- Experience with automation and AI deployment in HR workflows
- Comfort working in small, ambiguous, early-stage team environments and doing hands-on operational work
- Familiarity with Ashby product is helpful
Ashby Compensation & Benefits Highlights
The following summarizes recurring compensation and benefits themes identified from responses generated by popular LLMs to common candidate questions about Ashby and has not been reviewed or approved by Ashby.
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Fair & Transparent Compensation — Pay is positioned at market levels with a stated target around the 75th percentile by performance level, and the company shares how levels and compensation are determined. Feedback suggests compensation ranges are published on job postings and benchmarked using multiple data sources to improve clarity.
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Healthcare Strength — Health coverage is described as top-tier for U.S. employees and dependents with employer-paid premiums, with high-quality supplemental coverage provided internationally. Feedback suggests this breadth and cost coverage signals strong medical benefits.
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Equity Value & Accessibility — Stock options include a long post-termination exercise window intended to reduce pressure and increase flexibility. This structure can make equity more accessible over time.
Ashby Insights
What We Do
Ashby helps scaling companies achieve their ambitious growth targets. With Ashby, teams of all sizes can run a fast and efficient hiring process. Trusted by companies including Shopify, Snowflake, Notion, Zapier and Reddit We’re convinced there’s a lot of room for improvement in not just recruiting tools but people tools and, in general, how software products are built. There are two parts to this: the quality of the product and how the product is made. Let's start with outputs. We are continuously disappointed about the state of software products today —software should be more intelligent, powerful, and doing much more for us. Today, most business software is still a simple database with few delightful and truly helpful features. We also believe that productivity in software engineering hasn't increased nearly as much as it should have. Part of that is the lack of building blocks that can be reused across features and applications. The other part is how teams are organized and managed. We aim to innovate in both areas. Outside of the domain we're building for today (people software and, more specifically, recruiting software), Ashby is also an experiment in how fast a team can build great products over many, many years.
Why Work With Us
We have published our operating principles on our blog - they describe how we work at Ashby. They cover how we aim to run projects, spend time and make decisions. Beyond that we also look for specific attributes in new hires. Humble, Empathetic, Curious, Driven, Reliable, Transparent, Honest, and don't take themselves too-seriously
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