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FutureSight

Co-Founder & CEO - AI Accounting Agents for CPA Firms

LocationToronto, Ontario, Canada
DepartmentEntrepreneur in Residence for FutureSight Ideas
EquityIncluded
Company size51+ people
First seen1w ago
Last seen2d ago
The Opportunity
FutureSight is seeking a Co-Founder & CEO to lead Crossfoot, an AI-native accounting agent platform. This is a co-founder partnership with meaningful founder equity, not a salaried executive role.
About the company
Crossfoot is agentic accounting for small-to-mid CPA firms; a segment where accountant shortages are structural, client intake is capped by production headcount, and the manual close and tax prep workflow consumes the majority of senior staff capacity. Crossfoot connects to the tools firms already use (QuickBooks Online, Xero, Drake) and delivers finished work products ready for partner review, without requiring system migration or enterprise-scale implementation.
Market Context
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We didn’t just build a thesis; we validated it directly with the market. We’ve spoken with CPA firm managing partners, CAS leads, and tax preparers. The key insights:
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The “why now” is structural, not hype: the profession lost 300,000+ professionals from 2020–2024, and the replacement pipeline has shrunk ~33% in a decade. Firms now cap new-client intake by production headcount rather than demand. They turn away winnable work they can’t staff. Meanwhile, CAS (advisory) revenue is projected to reach 30% of the firm’s revenue by 2026.
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Senior accountants spend 40%+ of their time on document intake and workbook compilation — $90K staff doing $20/hour data entry — while month-end close runs 10–15 business days on a pure manual process.
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Early AI adopters in accounting already earn 39% more revenue per employee. The gap between firms that move and firms that don’t is compounding now.
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We are targeting a large, fragmented, structurally underserved market. The total addressable market is an estimated $1.5B+ across 87,000+ US accounting firms, with a focused beachhead SAM of $400M+ (small/mid firms).
About FutureSight
FutureSight is a leading venture builder that co-creates world-class software companies with values-driven entrepreneurs from inception to exit. We are a team of founders, operators and designers with experience successfully bringing software to market at scale.
You’ll co-create with a proven studio team, led by John Carbrey (4x entrepreneur, $100M ARR), Krista LaRiviere (3x exited, E&Y Top Women Entrepreneur), Alan Smith (Strategyzer co-founder, $120M in products built), Prathna Ramesh (former MD of Maple Leaf Angels, $275M in follow-on capital), and Johnny Tong (0-to-1 builder, acquired by SAP and Stripe) bring a rare combination of operator exits, institutional investing, and AI product depth.
The Partnership
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Founder equity with meaningful ownership from inception
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Pre-seed capital committed by FutureSight for early hires and MVP development, with potential for follow-on funding
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Venture building resources, including embedded design, engineering, growth, and fundraising support from day one
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Investor and advisor network across vertical AI and early-stage capital markets
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A true co-creation model in which you operate as CEO with FutureSight’s cross-functional team as your partner
What you’ll own
As Co-Founder & CEO, you will set the venture’s direction and lead its execution.
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Strategy — Refine the ICP, size-tiered pricing model, and product positioning
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Customer Development — Lead pilots with managing partners, CAS leads, and outsourced-accounting/BPO operators at small-to-mid CPA firms, convert them to paid engagements, and build the referral-led go-to-market motion
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Product — Partner with the FutureSight product and engineering team to ship V1 and iterate on user feedback
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Capital — Lead the seed raise, supported by FutureSight’s network and traction
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Team — Recruit and lead the founding team, and establish the cultural foundation of the company
Co-Founder Profile
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Previous founding experience at a venture-backed company
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Demonstrated success in B2B AI or B2B SaaS go-to-market, including consultative, relationship-driven sales and customer engagement
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Fundraising fluency, with the ability to develop investor narratives and close capital
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Proven ability to attract, develop, and retain top talent
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Clear-eyed understanding of the risks and demands of co-founding a venture-backed company
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Deep accounting domain expertise, with hands-on experience managing close processes, tax preparation, workpapers, and client accounting services within CPA firms.
How to Apply
Please submit your resume, LinkedIn profile, and a brief note on why this venture aligns with your goals as a founder. We will move quickly for the right candidate.
Legal
FutureSight is committed to diversity, equity, and inclusion. We welcome applicants of all backgrounds and experiences.
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