Motivate Venture Capital

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 QuickBooks 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.

Role Overview: Boom is seeking a Controller to assist our internal Fractional CFO Services practice. This role will serve as both operator and architect—delivering hands-on financial advisory to small business clients while building a scalable infrastructure to support Boom’s product development and deal execution. This role will be focused on transforming disorganized books into actionable, investor-grade financials—laying the foundation for AI automation and faster deal processing.

Responsibilities:

• Lead the migration of offline accounting systems (e.g., QuickBooks Desktop) to cloud-based platforms such as QuickBooks Online.
• Optimize client chart of accounts to improve financial reporting clarity and consistency.
• Set up third-party tools and automations to enhance bookkeeping efficiency and accuracy.
• Implement systems, processes, and best practices to modernize client financial operations.
• Manage month-end close, general ledger reconciliations, create budgets and forecasts, and deliver actionable financial insights to small business owners while adhering to GAAP compliance.
• Provide advisory support to drive EBITDA improvements and increase enterprise value.
• Collaborate with Boom’s product and engineering teams to document workflows and standardize accounting processes in preparation for future automation.
• Build and scale the CFO Services practice, transitioning from individual contributor to team leader by hiring, mentoring, and managing staff and AI-enabled resources.

Qualifications:

• Bachelor's degree in accounting or finance; CPA preferred but not required.
• 5+ years of progressive accounting experience, including Big 4 public accounting, industry roles at a small to medium sized business, or FP&A.
• Advanced proficiency in QuickBooks Online and Desktop, with hands-on experience in ledger clean-up, migrations, and financial system optimization.
• Prior experience as a Controller, Accounting Manager, or fractional CFO serving SMB clients.
• Strong understanding of small business financial reporting, GAAP month-end close, budgeting, and cash flow management.
• Familiarity with M&A processes, including transaction readiness, quality of earnings analysis, and buyer financial due diligence (preferred).
• Clear, practical communication skills, with the ability to explain financial insights to non-financial business owners.
• Proven experience documenting financial processes and building scalable operational workflows.
• Process-minded and comfortable working in a fast-paced, early-stage environment focused on iteration and growth.
• Chicago-based or willing to relocate within the next 3 months.

What We Can Offer:

• Competitive Compensation: $120K–$150K (Base Salary + Bonus)
• Equity Upside: Participate in Boom’s growth through meaningful equity—building long-term ownership, not just a paycheck.
• Foundational Role: Build and lead a core service offering with direct ownership and autonomy.
• Leadership Path: Hire and lead your own team as you transition from player to coach.
• Chicago HQ: Work from our Chicago downtown office.

Why Boom?

• Solving a $10 Trillion Problem: Baby boomers own over $10 trillion worth of small businesses, yet 80% will fail to sell. Boom exists to change that.
• Building an End-to-End AI Solution: Our platform combines human expertise with AI-driven automation to make small business succession scalable.

Venture-Backed Growth: Join a fast-paced, VC-backed startup redefining the future of small business M&A.