Chief of Staff

Job Description

Job Description

About Warden AI

Warden AI helps HR Tech vendors, staffing firms, and employers prove and improve the fairness, accuracy, and compliance of their AI hiring systems. In a fast-changing regulatory environment, organizations need a trusted partner to validate their AI, and Warden is quickly becoming the default solution.

In 2025, Warden grew from 4 to 40 customers. In 2026, we’ve already more than doubled ARR and are growing faster every quarter. That growth is driven not just by market demand, but by something rarer: a genuine network effect. Customers want to promote working with Warden because it helps them win their own deals.

We're now a team of 9, carrying the operating load of a much larger company. This role exists to change that.

Why This Role Is Different

This role combines two things that are often separate: working alongside the CEO on Warden's biggest priorities, and directly owning the operational foundations of the company. You'll move between the two constantly.

Warden has reached the point where a lot of important things still live in people's heads, but they can't stay there as we grow. Your job is to help turn that into an operating system that lets Warden become a much bigger company without becoming a chaotic one.

Here's what you'll step into:

• Real proximity . You'll work with the CEO daily, sit in on the decisions, and represent him externally when it matters.
• Genuine scope . Finance, people, reporting, CRM, investor updates, partnerships, market research, the advisory council. Few roles at any stage touch this much of a company.
• A blank page, on purpose . We don't have in-house Finance, People, Legal or Business Operations teams today. We have good external support, but much of our internal operating infrastructure is still to be built. You'll build it, improve it as we grow, and decide what should eventually be handed to dedicated owners.
• Real traction . We've found strong product-market pull, built excellent customer references and grown quickly. You're joining to scale something that's working.
• A chance to mature a company . A lot of important things still live in people's heads. Your job is to turn that into an operating system that makes Warden more rigorous and scalable without making it bureaucratic.

We're 9 people, so you'll work closely with everyone. Some days that means working with the CEO on a new market or partnership. Other days it means fixing payroll, sorting out a policy or cleaning up a process that isn't working. Both are part of building a great company.

The test we apply to this role is simple: can we say "go and sort that out" about almost anything, and stop thinking about it?

What You'll OwnOperations & finance

• Manage Warden's financial operations end to end, working with our external accountants, ensuring the right funds are in the right place, confirming payroll and managing pension schemes
• Own and maintain the financial model
• Manage metrics, reporting and the dashboards the team runs on
• Own CRM processes, hygiene and reporting in Attio
• Build the operational processes Warden needs as it grows, keeping them as simple as possible while making sure the important things are done properly

People

• Own day-to-day people operations, working with external support where needed, including policies, onboarding and our HRIS
• Make sure Warden has the right foundations in place as we grow beyond our first 20 hires
• Help make Warden a company people want to stay at, without adding unnecessary process or bureaucracy

CEO leverage

• Write investor updates
• Conduct outreach on behalf of the CEO to partners, prospects, advisors and regulators
• Spearhead new initiatives alongside the CEO. Right now that means project-managing our data partnerships and establishing Warden's advisory council. In six months it will mean something else
• Conduct market research into new segments as we expand across the hiring market
• Gradually reduce the number of things that depend on the CEO personally

Everything else

• Take on important projects and problems that don't have an owner yet
• Work out what actually matters, rather than trying to fix everything at once
• Sometimes you'll own something yourself. Sometimes you'll build the process, find the right long-term owner and hand it over
• Leave behind systems that work without you, rather than becoming the person who has to hold everything together

You'll Be a Great Fit If…

• You have 4–8 years across startups, operations, Chief of Staff, consulting or founding-team roles, including meaningful hands-on experience owning business operations rather than just advising on them
• You're an operator first. You'd rather fix the broken payroll run today than write a memo about payroll strategy. You can do both, but you know which one this week needs
• You can write. Investor updates, partner emails and internal docs go out in your words, and we shouldn't need to rewrite them
• You're comfortable with numbers. A financial model doesn't intimidate you, and you'll notice when something doesn't reconcile
• You have the judgment to speak on the CEO's behalf without checking first every time, and the instinct to know when to check
• You know how to prioritize. You'll always be able to find ten things that could be better; you can work out which two really matter, what can be "good enough", and what isn't worth doing at all
• You're systematic and resourceful. You leave behind processes, not heroics, but you don't over-engineer solutions a 12-person company doesn't need
• People trust you with sensitive things. You're discreet, low-ego and understand the responsibility that comes with seeing almost everything happening inside the company
• You're comfortable with genuinely unglamorous work. Building operational rigor sometimes means getting into the details and doing the admin yourself, particularly at this stage
• You want to be close to how a company actually gets built and get satisfaction from making the whole organization work better

This Role Isn't for You If…

• You want a strategy role. A meaningful part of this job is hands-on operations, and that doesn't disappear once you've proved yourself
• You see Chief of Staff primarily as a route into Sales, Product or another function in 18 months. There is significant room to grow here, but the natural path is deeper into company-building and operations: toward COO, Head of Operations or broader operational leadership
• You need a defined playbook or clear boundaries around your remit
• You're uncomfortable getting into the details of finance, payroll, HR or company administration
• You'd rather influence decisions than own outcomes
• You want fully remote

What Success Looks Like in Your First 90 Days

• Financial operations run without the CEO in the loop, including payroll, accountants and pensions
• Metrics and reporting are automated enough that the weekly numbers arrive without anyone chasing them
• The advisory council has a shortlist, an approach plan and first conversations underway
• The foundations of our people operations are in place, with the biggest gaps identified and addressed
• You've found and fixed at least one thing nobody asked you to look at
• The CEO's list of "things only I can do" is meaningfully shorter

Over time, the bigger measure is simple: Warden should feel like a significantly more mature company internally without feeling like a more bureaucratic one.

Compensation & Benefits

• $120,000–$160,000 base salary
• Meaningful equity in a rapidly growing business (4-year vest, 1-year cliff)
• Healthcare coverage
• 18 days paid time off, plus 8 US public holidays and sick leave
• Flexible / hybrid working environment
• Significant room to grow. For someone who excels in the role, the natural path is toward COO, Head of Operations or broader operational leadership as Warden scales

Hiring Process

We move quickly and aim to make this a thoughtful, structured experience. It's as much about you assessing us as it is the other way around.

1. Founder Screen (20 min) – Intro chat with our CEO to align on your background and the role.
2. Operating Deep Dive (45 min) – A conversation about messes you've cleaned up. We'll want specifics: what broke, what you did, what you personally owned and what you left behind.
3. Written Exercise – Draft an investor update from a set of raw numbers and notes we provide. Take an hour, not a day. We'll discuss it together.
4. Working Session (45 min, ideally in person) – Sit with the CEO on a messy, live operating problem. We'll be interested not just in how you solve things, but how you decide what matters, what can wait and what doesn't need doing at all.
5. Reference Checks & Offer – We move quickly from references to a clear offer and 90-day success plan.