Careers

We are not hiring for headcount.

Cromwell is building the operating infrastructure for a new kind of accounting firm: AI-powered delivery, CFO-grade standards, and a client base that includes professional athletes, funded startups, and creator-economy businesses. We hire for craft. We promote on output. We do not tolerate mediocrity at any level.

The Standard

What we look for

Cromwell operates at the intersection of financial services, regulated markets, and AI-powered delivery. The people who thrive here are not looking for a job. They are looking for a platform to do the best work of their careers. We are hard to get into, deliberately so.

Precision under pressure

Financial work is unforgiving. We need people who deliver clean output when the deadline is real and the stakes are a client's business.

Ownership without prompting

We do not manage output at the task level. If something is yours, it gets done. If something is broken, you fix it before being asked.

Comfort with ambiguity

Cromwell is early-stage. The platform is being built in real time. The operators who succeed here thrive when the playbook is incomplete.

High ceiling, low ego

We hire people who are exceptional at their craft and completely uninterested in making it obvious. Results speak. Resumes are a starting point.

Open Roles

Four seats. One bar.

Operations, Client Delivery

Bookkeeper / Operator

Full-Time, Remote / Jupiter, FL or Remote

The Operator is the core delivery unit at Cromwell. You own a book of 20-30 client accounts and are responsible for keeping every one of them closed, reconciled, and current. The Cromwell Ledger platform does the heavy lifting on categorization, your job is judgment, quality control, and the client relationship.

This is not a data-entry role. The right candidate understands that they are the last human between an AI-powered workflow and a client's financial statements.

WHAT YOU WILL OWN

  • +Monthly close for a full book of client accounts, every book closed by the 15th, no exceptions
  • +Review queue management in the Cromwell Ledger, clearing AI-categorized transactions, flagging exceptions
  • +Bank and card reconciliation across Plaid, Ramp, Mercury, and QBO-connected accounts
  • +Client onboarding via the Foundation Interview, framing a new book in under 15 minutes
  • +Anomaly surfacing, spotting what the engine doesn't flag before the client does

WHAT WE ARE LOOKING FOR

  • +2+ years bookkeeping experience; QBO ProAdvisor certification preferred
  • +Comfortable operating inside software workflows, you learn new platforms fast
  • +Track record of managing multiple client books simultaneously without errors
  • +Detail-obsessed but not slow, you close on time, every time
  • +Athletes, creators, or startup clients in your background is a strong plus
  • +Thrives in an async-first, remote environment with minimal supervision

COMPENSATION STRUCTURE

Base Salary

$55,000 - $75,000

Structure

W-2 or 1099, negotiable

Work Model

Remote-first

Equity

Not offered at this tier

Review

Performance review at 90 days

Advisory, Principal

CPA / CFO Advisor

Full-Time, Remote / Jupiter, FL or Remote

The CFO Advisor is the senior client relationship at Cromwell. You own the close approval, the Stakeholder Update review, and the quarterly advisory session. Operators run the books. You are the judgment layer and the face of the firm.

This role is not a reviewing manager. You are a fractional CFO, one who happens to have an AI-powered platform doing the bookkeeping underneath you.

WHAT YOU WILL OWN

  • +Monthly close approval across a portfolio of Growth and Enterprise client books
  • +Edit and release of the AI-drafted monthly Stakeholder Update, your voice, your sign-off
  • +Quarterly advisory sessions: cash runway, tax posture, KPI trends, strategic guidance
  • +Escalation point for all judgment calls flagged by Operators
  • +Client retention, you are the relationship that makes clients renew
  • +Onboarding review for complex or multi-entity books

WHAT WE ARE LOOKING FOR

  • +Active CPA license in good standing, non-negotiable
  • +5+ years in public accounting, fractional CFO, or FP&A; startup or sports/entertainment exposure preferred
  • +Client-facing experience, you have held advisory relationships, not just completed returns
  • +Comfortable delivering bad news clearly and early, clients pay for honesty, not comfort
  • +Fluent in QBO, multi-entity structures, cash vs. accrual nuance
  • +Florida CPA license or ability to obtain, preferred given our domicile

COMPENSATION STRUCTURE

Base Salary

$95,000 - $130,000

Performance Bonus

5% net profit share

Equity

15% vesting, available for right candidate

Work Model

Remote-first; Jupiter FL preferred

Review

90-day and annual

Revenue, Business Development

Sales / Dealmaker

Commission, 1099 / Remote, National

The Dealmaker role is commission-only, permanently. This is not a pipeline toward a salaried position. It is a high-upside revenue share for people who close deals and want to be paid for the life of what they bring in.

You are selling a service that clients genuinely need, at a price point that is easy to justify. The pitch is not hard, the close is.

WHAT YOU WILL OWN

  • +Prospecting and outreach to startups, athletes, and creator-economy businesses in your network
  • +Managing deals from first conversation to signed MSA, you own the full cycle
  • +Handing off signed clients cleanly to the Operator team, no dropped balls at transition
  • +Building a referral network that generates inbound over time

WHAT WE ARE LOOKING FOR

  • +A network that includes founders, athletes, agents, or creator managers, warm pipeline, not cold email lists
  • +Experience closing professional services, SaaS, or financial services engagements
  • +Comfortable explaining accounting and advisory value without being a CPA yourself
  • +Self-managed, self-motivated, there is no SDR team feeding you leads
  • +Integrity: you close clients who are a genuine fit, not every warm body

COMPENSATION STRUCTURE

Month 1 Commission

20% of first month's MRR

Ongoing Recurring

5% of MRR for life of client

Example: $2,000/mo client

$400 Month 1, $100/mo forever

Structure

1099, no base, no cap

Clawback

90-day client retention required

Engineering, Platform

Full-Stack Engineer

Full-Time, Contract / Remote

You will be building the Cromwell Ledger, an AI-powered internal platform that enables one bookkeeper to run 30 client books. The stack is Next.js 15, TypeScript, Postgres (Neon), Inngest for job orchestration, and the Anthropic Claude API for the execution engine.

This is not a maintenance role. You are building from a clean TRD. The 90-day build plan is fully specified across four milestones: skeleton, data ingestion, AI engine, and close/ship.

WHAT YOU WILL OWN

  • +Foundation Interview wizard, multi-step client onboarding with COA generation via Claude API
  • +Integration hub, Plaid, QBO, Ramp, Gusto, Stripe connectors with webhook ingestion and 24-month backfill
  • +Review queue UX, keyboard-first transaction review with AI rationale display
  • +Batch API pipeline, nightly categorization runs, confidence scoring, correction memory
  • +Report generation, branded PDF rendering via HTML templates, advisor release flow
  • +Admin plus AI spend metering, per-book cost tracking and budget alerts

WHAT WE ARE LOOKING FOR

  • +Next.js plus TypeScript, fluent, not just familiar. App Router required.
  • +Postgres, comfortable with RLS, migrations, and relational data modeling
  • +API integrations, you have built OAuth 2.0 flows and webhook consumers before
  • +Anthropic / LLM APIs, experience with tool use, structured outputs, and Batch API strongly preferred
  • +Background in fintech or financial data handling, you understand why data integrity and audit trails matter
  • +1-2 person team mentality, you scope, build, test, and ship without a PM holding your hand

COMPENSATION STRUCTURE

Build Phase (Days 0-90)

$15,000 - $25,000 / mo

Maintenance (Post-M4)

$5,000 - $10,000 / mo

Structure

Contract, 1099

Equity

Available for exceptional candidates

Stack

Next.js, Postgres, Inngest, Claude API

How We Hire

A process as direct as our standards.

01

Reach out

Send your resume and a single paragraph, not a cover letter, explaining what you have built or closed, and why Cromwell is the right next move for you specifically.

02

First call

30 minutes. We will tell you exactly what the role requires. You will tell us exactly what you have done. No HR screen. You speak directly with the founding team.

03

Work sample

A short, paid exercise relevant to the role. Operators close a sample book. Engineers build a small feature. Advisors review a real (anonymized) Stakeholder Update. Paid at $150 flat.

04

Offer or pass

We move within 48 hours of the work sample. We will tell you yes or no, and we will tell you why. We do not ghost candidates.

Ready to apply?

Send your resume and one paragraph through our contact page. We read everything.

GET IN TOUCH