Remote Cfo Insurance Jobs in Toronto, ON (NOW HIRING)

FutureSight Ventures is a venture builder that cofounds and invests in B2B AI software companies. We sit at the intersection of fund management and venture creation: we run a fund with LPs, we incubate and incorporate new ventures, and we provide ongoing financial, operational, and strategic support to the companies in our portfolio.

We are hiring a Chief Financial Officer to own the financial spine of the firm, the fund, the management company, and the venture-facing work that makes our model distinctive.

This is a hands-on, broad-scope CFO role. You will lead fund accounting and LP reporting, drive corporate and tax compliance, manage treasury and insurance, and partner closely with the investment team on capital formation, spin-outs, cap table mechanics, follow-on financings, and equity issuance. You will oversee a small finance and accounting team — including our bookkeeper, our accountant, and external partners — and be the firm's senior financial voice with LPs, ventures, and outside counsel.

The right person is comfortable moving between high-stakes deal work, negotiating an investment agreement and leading a disciplined operating cadence.

Firm Accounting & LP Reporting

• Treasury & liquidity: bi-weekly cash reviews, inter-account transfers, and banking relationships.
• Monthly fund accounting: NAV, capital accounts, and fund financials.
• Quarterly LP financials package: LP report (narrative, performance, portfolio).
• Capital calls, distributions, and waterfall mechanics.

Compliance & Tax

• Corporate compliance across FutureSight entities: annual filings, incorporation, board governance, registered agents, and entity housekeeping.
• Budgeting and cash flow forecasting to support LP reporting.
• US and Canadian tax compliance (federal, provincial, state, local), including LP K-1s.
• Manage external lawyers, tax accountants, and advisors on deadlines and quality.

Treasury, Insurance & Record Keeping

• Own the insurance program: D&O, E&O, cyber, general liability, and venture-related coverage.
• Keep corporate records, board consents, and finance documentation organized and audit-ready.

Spin-Outs & Venture Investment  

• Lead spin-outs end-to-end: negotiate documents, incorporate ventures, and run US compliance and registration.
• Oversee 409A valuations, option grants, and approvals across FutureSight and ventures.
• Negotiate follow-on investments with portfolio ventures in coordination with the investment team and outside counsel.

Venture Management & Portfolio Finance

• Senior finance interface with ventures on financings, controls, compliance, and operations.
• Maintain portfolio cap tables and model rounds, option pools, and secondaries.
• Monthly consolidated reporting: capital deployed, venture runway, and upcoming funding needs.
• Manage equity grants across ventures and FutureSight with counsel.
• Drive venture compliance and governance, including incorporations.

Team Oversight

• Manage the Accountant/Bookkeeper on credit cards, AP/AR, and day-to-day accounting.
• Build the operating model: what stays in-house, what's delegated, and what goes to outside firms (fund admin, tax, legal).
• Optimize process and tooling.

• 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.

• A senior seat at a venture firm with a differentiated model — fund, venture builder, and operating support under one roof.
• Direct partnership with the Managing Partner on strategy, fundraising, and venture creation.
• Competitive compensation 
• Preference for Toronto, Canada location

Send a resume and a short note on why this role and why now. We review applications on a rolling basis and aim to respond within two weeks.