Back office and operations for Seed to Series A companies.
Saving founders countless hours of toil.
Tools we work with
What we do
Most companies hire finance and people teams too early, then spend the next year managing the people they hired to do the work. Headroom gives founders their attention back by building the operations you need without adding another person to manage.
Financial close
Clean books on time, every month. Chart of accounts, GL hygiene, and reporting that reflects how the business runs.
Payroll
Domestic and global payroll, commissions, and contractor payments on the right platform. Multi-state and international tax handled.
Spend and expense
Ramp or Brex implemented properly. Real expense policy, approval workflows, card controls. Cash-burn visibility before it's a problem.
Accounting systems
The right tools, configured correctly. We set up and optimize your accounting stack with strong opinions about what belongs in it at your stage.
HR ops and onboarding
Offer letters, onboarding checklists, benefits enrollment, offsite planning. The operational layer that makes your first 50 hires feel like a real company hired them.
Compliance
Equity admin, contractor management, federal and local tax, sales tax nexus, 1099s. The unglamorous stuff that creates six-figure surprises when ignored.
How it works
Every Headroom engagement is a defined 60 to 90 day sprint with a clear scope agreed upfront. You know what you're getting, when it ends, and what the company looks like when we're finished. No open-ended hourly work.
We work with companies where the founder or a generalist is currently holding the finance and operations function, and where that arrangement is starting to break. If that sounds familiar, get in touch.
How we're built
Fewer clients, better service. 99% of service firms get replaced because they never learn the business. Headroom is purpose-built to learn yours and grow with it.
No rotating staff, pods, account managers, or offshore teams. The person on the intro call is the person building your systems.
Direct line to the person doing the work. No internal approvals or escalation chains.
Context compounds. You explain how things work once, and the person who heard it is the one building the systems around it.
No incentive to drag things out or invent reasons to stay. The win condition is leaving you with systems that run on their own.
How we compare
If you've raised and the back office is starting to break, you're probably already weighing one of these. Here's where Headroom fits.
vs. Internal Hire
Most early-stage companies mis-hire their first finance or people seat. They bring in a controller when they needed a Head of Finance, or a senior leader who ends up doing AP and onboarding because no systems exist underneath them. Either way, it's a six-figure mistake the company carries for years.
Headroom builds the base in 60 to 90 days. The hire you make after, when you're ready, walks into a real foundation and ramps in weeks instead of quarters.
Read the full breakdownFirst-year cost of an internal ops hire
Finance or people leader at Seed to Series A. Doesn't include recruiting fees or the cost of a mis-hire.
vs. Fractional CFO
The fractional CFO value prop has gotten fuzzy. Most of what they delivered was analysis and narrative, and a founder with the right tools can produce 80% of that. What founders can't do is build payroll, clean up a chart of accounts, or implement Ramp correctly.
Board-level strategic input comes from your investors and your founder network. Headroom does the operational work neither of them will touch.
Read the full breakdownWhere each model fits
Reading
Writing on the back-office decisions founders face after a raise. The hidden cost of the first ops hire. Why the infrastructure layer comes before the strategy layer.
Playbook
Managing AI Spend for Startups
The tokenmaxxing herd is breaking. Uber blew through its 2026 AI budget in four months. Microsoft pulled Claude Code licenses despite engineers preferring them. The tactical moves and investor narrative founders need to manage AI infrastructure spend without bankrupting the company.
ReadWalkthrough
Five Claude Finance Agents, Walked Through Step by Step
Concrete walkthroughs of month-end close, reconciliation, variance, board prep, and analysis on a fictitious 22-person Series A SaaS company. Real prompts, sample outputs, and where each agent falls short.
ReadPlaybook
The Post-Raise 90-Day Back Office Playbook
What to set up, in what order, with which tools. Deep teardowns of Mercury, Ramp, Gusto, Rippling, Deel, QBO, Pulley, Carta, and Anrok. Three decision frameworks, scenarios for non-standard companies, and an interactive checklist.
ReadComparison
Internal Hire vs. Headroom
Why your first ops hire costs more than salary. The hidden drag on your attention, cap table, and headcount when you hire a Head of People, Head of Ops, or first finance lead post-raise.
ReadComparison
Fractional CFO vs. Headroom
Two different jobs. Fractional CFO firms handle ongoing strategy. Headroom builds the operational back office that should exist underneath it. Which one you need first.
ReadFounder FAQ
Headroom is a back-office buildout service for post-raise founders. We run the finance, people, and operations build that turns founder-maintained systems into a back office that functions on its own. Fixed scope, defined deliverables, one person does the work, then leaves.
Seed to Series A companies, 10 to 40 employees, US-based, post-raise. Typically founders who just closed a round and realized the back office they've been holding together is about to break.
Different category. Fractional CFO firms like Pilot, airCFO, and Burkland provide ongoing financial strategy and board reporting. Headroom builds the operational back office underneath the strategy layer: payroll, close, spend, equity, compliance. Most post-raise companies need the infrastructure built first.
Modern stack only. Ramp, Rippling, Mercury, QBO, Brex, Carta, Pulley, Gusto, Deel, Anrok. No Bill.com, no NetSuite.
Get in touch
If you've recently raised and your back office hasn't kept up, we'd like to hear from you. Fill out the form and we'll follow up within a couple of days, or email us directly at [email protected].