CFO for Mission Driven Small Business (Part-Time, Contractor)

Dear Future CFO of BostonSpeaks, Let’s be clear from the start. This is not a traditional CFO role. We’re looking for a CFO who’s forward-thinking, tech-savvy, emotionally intelligent, and embraces authenticity over perfection. Someone who understands that finance is not just numbers, it’s psychology, behavior, and decision-making under pressure. We need you to help create clarity, calm, and better financial decisions. BostonSpeaks helps leaders overcome public speaking anxiety. We are proud to be one of the top public speaking training firms in Boston, MA. We have helped organizations from RE/MAX, ASICS, Hubspot and numerous more. Our website is bostonspeaks.com At BostonSpeaks, each team member challenge ourselves personally. We question our own patterns, assumptions, and limiting beliefs, not because it’s trendy, but because growth demands it. We care about the work and about each other. We get emotional with our team. We talk about what’s real. We don’t leave our humanity at the door just because numbers are on the table. This isn’t a “keep it professional at all costs” culture. It’s a stay present, stay honest, and do excellent work culture. If that makes you think, “Yes, finally,” this might be your place. If it makes you uncomfortable, that’s information too. Who You Are (this is how we weed people out) -You love translating financial data into plain English decisions -You’re energized by small, purpose-driven teams where your work actually changes behavior -You use modern tools, dashboards, and systems and you’re opinionated about them -You’re comfortable challenging leadership without ego -You see cash flow, profit, and forecasting as tools for freedom, not fear -You enjoy teaching leaders how to think financially, not just what the numbers say -You want to be part of a small team and working closely with everyone. -You want to lead the finance department and shape it to be the best it can be. -Experience in online coaching or education is a plus, including roles with executive coaching, corporate training programs, online course creators, or virtual learning platforms. How to Apply (read this carefully) STEP 1: Make a loom/sendspark/… video introducing yourself, telling us - Why are you interested in working with BostonSpeaks? - Your experience in finance and leadership roles - Why do you think you would be a good cultural fit for our company? - What are your expectations? Step 2: Assume BostonSpeaks currently generates $1.4M annual revenue with $280,000 profit. Our 1-year goal is to reach $2.1M annual revenue with a 30% profit margin. With only this information: - What would be the first questions you would ask to understand our business financially? - What areas would you focus on first in this role? (Top 3 priorities) - Based on the limited information above, how would you roughly assess our likelihood of achieving the 1-year goal? (High-level is fine; we’re evaluating your thinking, not precision.) -Team BostonSpeaks p.s. if you apply, please address it to Sophie who will be managing our conversations. Apply tot his job