Fractional CFO – Chief Financial Officer

FutureSight

CFO leading finance and accounting for FutureSight, a venture studio investing in B2B AI software companies. Overseeing fund management, compliance, and team operations.

Posted 5/15/2026full-timeRemote • 🇨🇦 CanadaLeadWebsite

About the role

Key responsibilities & impact

Lead fund accounting and LP reporting, drive corporate and tax compliance, manage treasury and insurance.
Partner closely with the investment team on capital formation, spin-outs, cap table mechanics, follow-on financings, and equity issuance.
Oversee a small finance and accounting team including our bookkeeper, our accountant, and external partners.
Be the firm's senior financial voice with LPs, ventures, and outside counsel.
Own the insurance program.
Manage external lawyers, tax accountants, and advisors on deadlines and quality.
Maintain portfolio cap tables and model rounds, option pools, and secondaries.
Drive venture compliance and governance, including incorporations.

Requirements

What you’ll need

Experience: 8+ years in finance leadership roles, with meaningful exposure to venture capital, venture studio, or private equity environments — and ideally direct experience with both fund-level and operating-company finance.
Deal fluency: comfort negotiating investment and spin-out documents alongside counsel, and understanding the mechanics of SAFEs, priced rounds, option pools, 409A, and cap tables.
Fund accounting and LP reporting: fluency with fund mechanics, NAV, capital calls/distributions, waterfall, and LP-grade quarterly reporting.
Compliance and tax: able to drive corporate compliance, sales tax, and annual tax filings across multiple entities, and to manage outside tax and legal advisors.
Operating discipline: you actually enjoy the recurring rhythm — monthly close, bi-weekly treasury, quarterly LP package — and you instill that rhythm in the team.
Team leadership: experience managing a small finance and accounting team and external partners; coaches and raises the bar of those around them.
Builder's bias: comfortable with ambiguity, white space, and a portfolio of work that ranges from strategic to in-the-weeds.
Credentials: CPA required; MBA, CFA, or JD/tax background a plus but not required.

Benefits

Comp & perks

🌐 Worldwide ❌ Jobs You've Hidden ⭐️ Saved Jobs ✅ Applied Jobs ✉️ Email Alerts 👤 Account FutureSight Website LinkedIn All Job Openings 11 - 50 employees 🤖 Artificial Intelligence 🤝 B2B Venture Capital
Artificial Intelligence
B2B FutureSight is a venture studio that co-founds and funds B2B AI ventures, building scalable world-class businesses with values-driven leaders. Based in Toronto, New York, and San Francisco, FutureSight collaborates with entrepreneurs by providing a supportive community of experienced product leaders, business designers, engineers, marketers, and growth hackers. This 'Dream Team' aids in refining ideas from inception to scale, developing co-founders into transformational leaders. FutureSight focuses on various sectors, including health tech, education tech, and fintech, offering a rigorous process for validating ideas and investing in great talent and concepts. Fractional CFO – Chief Financial Officer Job not on LinkedIn 🔥 1 hour ago 🇨🇦 Canada – Remote ⏰ Full Time 🔴 Lead 💸 Financial Planning and Analysis (FP&A) Apply Now Find Hiring Managers Customize resume + cover letter Report problem ☆ Save ☑️ Mark as applied ❌ Hide 📋 Description
Lead fund accounting and LP reporting, drive corporate and tax compliance, manage treasury and insurance.
Partner closely with the investment team on capital formation, spin-outs, cap table mechanics, follow-on financings, and equity issuance.
Oversee a small finance and accounting team including our bookkeeper, our accountant, and external partners.
Be the firm's senior financial voice with LPs, ventures, and outside counsel.
Own the insurance program.
Manage external lawyers, tax accountants, and advisors on deadlines and quality.
Maintain portfolio cap tables and model rounds, option pools, and secondaries.
Drive venture compliance and governance, including incorporations. 🎯 Requirements
Experience: 8+ years in finance leadership roles, with meaningful exposure to venture capital, venture studio, or private equity environments — and ideally direct experience with both fund-level and operating-company finance.
Deal fluency: comfort negotiating investment and spin-out documents alongside counsel, and understanding the mechanics of SAFEs, priced rounds, option pools, 409A, and cap tables.
Fund accounting and LP reporting: fluency with fund mechanics, NAV, capital calls/distributions, waterfall, and LP-grade quarterly reporting.
Compliance and tax: able to drive corporate compliance, sales tax, and annual tax filings across multiple entities, and to manage outside tax and legal advisors.
Operating discipline: you actually enjoy the recurring rhythm — monthly close, bi-weekly treasury, quarterly LP package — and you instill that rhythm in the team.
Team leadership: experience managing a small finance and accounting team and external partners; coaches and raises the bar of those around them.
Builder's bias: comfortable with ambiguity, white space, and a portfolio of work that ranges from strategic to in-the-weeds.
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Hard Skills & Tools

fund accountingLP reportingcapital formationcap table mechanicsSAFEspriced roundsoption pools409ANAVcorporate compliance

Soft Skills

team leadershipnegotiationoperating disciplinecoachingstrategic thinkingadaptabilitycommunicationquality managementrelationship managementproblem-solving

Certifications

CPAMBACFAJDtax certification