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

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

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

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

Boom isnt just cleaning up numbers; were boosting the numbers that matter. Our Succession as a Service platform pairs AI agents with human expertise to migrate decades-old QuickBooks files, uncover growth levers, and coach owners to maximize the value of their lifes work before they exit.

Thats why we need a Head of CFO Services who lives for turning chaos into clean data and EBITDA expansion. Youll be the financial heartbeat that polishes messy books, discovers profit drivers, and productizes every repeatable step into agent-powered workflowsso 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 SMBsmost without succession plans. Were 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 QuickBooks desktop ledgers and zero financial insight. Boom fixes thatand sells the company for more. Youll 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 youll 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 narrativeslift 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 ($125-150K 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, youre not just writing codeyoure 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, wed 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. Lets 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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