Director of CFO Services; AI-Native Investment Bank

Director of CFO Services for Boom (AI-Native Investment Bank)

Director of CFO Services for Boom (AI-Native Investment Bank)

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We’re an AI-native Investment Bank that is streamlining, democratizing, and accelerating the sale of legacy industrial businesses. Backed early by Motivate VC, we’ve rocketed from $0 to nearly $800K in ARR in under a year with over $200M in exclusive deals.

Boom isn’t just cleaning up numbers; we’re boosting the numbers that matter. Our “Succession as a Service” platform pairs AI agents with human expertise to migrate decades-old Quick Books files, uncover growth levers, and coach owners to maximize the value of their life’s work before they exit.

That’s why we need a Head of CFO Services who lives for turning chaos into clean data and EBITDA expansion. You’ll be the financial heartbeat that polishes messy books, discovers profit drivers, and productizes every repeatable step into agent-powered workflows—so our sellers walk away wealthier and prouder of their legacy.

Why Boom?

Ground-floor opportunity:
Be the architect and first operator of a high-impact revenue stream inside a venture-backed fintech.

Massive market:
Baby Boomers own over 2 million SMBs—most without succession plans. We’re changing that.

AI at the core:
Build intelligent agents that automate the entire FP&A process and strategy.

Equity & leadership:
Lead decisions, build the team, and get rewarded like a true partner.

Meaningful impact:
Help preserve legacies and save jobs by making transitions seamless.

Why this role exists

Baby-boomer-owned industrial businesses arrive with messy Quick Books desktop ledgers and zero financial insight. Boom fixes that—and sells the company for more. You’ll launch (and initially be) our Fractional CFO practice: migrate ledgers, close the books, advise owners, and turn every repeatable step into an AI agent.

What you’ll do (first 12 months)

• QB Desktop → Online migrations:
Clean up & convert 30+ companies per quarter with a 30-day, GAAP-quality close.

• Fractional CFO advisory:
Budgets, cash-flow forecasts, KPI dashboards, board-ready narratives—lift EBITDA & valuation.

• Ship “Autopilot Month-End” v1:
Document the process, partner with engineers, and automate at least one core task in 90 days.

• Own go-to-market:
Package tiers, close the first 10 reference clients, and build a 100-prospect pipeline.

• Collaborate with Product and Engineering to document workflows and standardize accounting processes in preparation for future automation.

• Build the team:
Hire/mentor 2-3 analysts and move from player-coach to GM of a scaled practice.

• Deal-side fluent — Comfortable with QoE schedules, WC pegs, and buyer Q&A.

• Process-to-product thinker — Write SOPs via AI today, automate them tomorrow.

• Industrial empathy — Can explain EBITDA in shop-floor English.

• Hustler at heart — Thrive in ambiguity and biased to action.

• Chicago-based (or willing to relocate) — Willing to relocate within the next 6 months.

What you get

• Competitive cash + Revenue share ($K Base + Bonus = $250K OTE)

• Budget to build your own bench of analysts & specialists.

• Joining a rocket ship with a category defining company.

• Quarterly steel-toe off-sites as often as slide decks.

Join Us

At Boom, you’re not just writing code—you’re helping millions of business owners secure their legacies. If you want to build something that matters and be part of a journey with limitless upside, we’d love to talk.

ANSWER THESE TWO QUESTIONS

• What is something society believes to be true that you do NOT believe to be true?

• What is the most difficult thing in your personal or professional life that you had to persevere through?

Apply now or DM us directly. Let’s build the future of small business M&A.

Seniority level

• Seniority level Director

Employment type

•

Employment type

Full-time

Job function

• Job function

Finance and Sales

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