Fractional CFO (Chief Financial Officer)

FutureSight•Toronto, ON

1d•Hybrid

About The Position

FutureSight Ventures is a venture studio that co-founds and invests in B2B AI software companies. We operate at the intersection of fund management and venture creation, running a fund with LPs, incubating new ventures, and providing ongoing financial, operational, and strategic support to our portfolio companies. We are seeking a Chief Financial Officer to oversee the financial operations of the firm, the fund, the management company, and the venture-facing activities that define our unique model. This is a hands-on, broad-scope CFO role. The successful candidate will lead fund accounting and LP reporting, manage corporate and tax compliance, oversee treasury and insurance, and collaborate closely with the investment team on capital formation, spin-outs, cap table management, follow-on financings, and equity issuance. You will manage a small finance and accounting team, including a bookkeeper, an accountant, and external partners, and serve as the firm's primary financial representative to LPs, ventures, and external counsel. The ideal candidate is adept at navigating high-stakes deal work, negotiating investment agreements, and maintaining a disciplined operating cadence.

Requirements

8+ years in finance leadership roles.
Meaningful exposure to venture capital, venture studio, or private equity environments.
Direct experience with both fund-level and operating-company finance.
Comfort negotiating investment and spin-out documents alongside counsel.
Understanding of SAFEs, priced rounds, option pools, 409A, and cap tables.
Fluency with fund mechanics, NAV, capital calls/distributions, waterfall, and LP-grade quarterly reporting.
Ability to drive corporate compliance, sales tax, and annual tax filings across multiple entities.
Experience managing outside tax and legal advisors.
Experience managing a small finance and accounting team and external partners.
CPA required.

Nice To Haves

MBA, CFA, or JD/tax background a plus.

Responsibilities

Lead fund accounting and LP reporting, including monthly NAV, capital accounts, and fund financials.
Manage treasury and liquidity, including bi-weekly cash reviews, inter-account transfers, and banking relationships.
Prepare quarterly LP financials packages, including narrative, performance, and portfolio reports.
Oversee capital calls, distributions, and waterfall mechanics.
Drive corporate compliance across FutureSight entities, including annual filings, incorporation, board governance, and registered agents.
Develop budgets and cash flow forecasts to support LP reporting.
Ensure US and Canadian tax compliance (federal, provincial, state, local), including LP K-1s.
Manage external lawyers, tax accountants, and advisors to ensure deadlines and quality.
Own the insurance program, including D&O, E&O, cyber, general liability, and venture-related coverage.
Maintain organized and audit-ready corporate records, board consents, and finance documentation.
Lead spin-outs end-to-end, including negotiating documents, incorporating ventures, and managing US compliance and registration.
Oversee 409A valuations, option grants, and approvals for FutureSight and its ventures.
Negotiate follow-on investments with portfolio ventures in coordination with the investment team and outside counsel.
Serve as the senior finance interface with ventures on financings, controls, compliance, and operations.
Maintain portfolio cap tables and model rounds, option pools, and secondaries.
Provide monthly consolidated reporting on capital deployed, venture runway, and upcoming funding needs.
Manage equity grants across ventures and FutureSight with counsel.
Drive venture compliance and governance, including incorporations.
Manage the Accountant/Bookkeeper on credit cards, AP/AR, and day-to-day accounting.
Build the operating model, defining what stays in-house, what is delegated, and what is outsourced (fund admin, tax, legal).
Optimize processes and tooling within the finance function.