Co-Founder & CEO — AI-Native Accounting Firm
The Opportunity
FutureSight is seeking a Co-Founder & CEO to lead Fieldstone, an AI-native accounting firm. This is a co-founder partnership with meaningful founder equity, not a salaried executive role.
Fieldstone is an accounting firm built from a blank page around an agent fleet. Agents run bookkeeping, reconciliation, workpapers, and first-pass tax returns continuously, and every human in the firm sits in a reviewer seat: applying judgment, signing off, and owning the client relationship. You bring your client relationships and your craft. A FutureSight technical co-founder works alongside you inside the practice, automating the work as you do it, so the product is built from real engagements from day one.
Market Context
US accounting services is a $150B industry, with an estimated $29B serviceable market across 900K US and Canadian businesses in the $1-20M revenue band. Demand is growing while supply collapses: over 300,000 accountants have left the profession since 2020, CPA exam candidates are down more than 30% over the past decade, and roughly 75% of active CPAs are retirement-eligible. Regional firms are turning away mid-market clients because they no longer have the capacity to serve them. That is Fieldstone's entry point.
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 venture building 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
Founder equity with meaningful ownership from inception
Pre-seed capital committed by FutureSight for early hires and agent development, with potential for follow-on funding
A technical co-founder embedded in your practice from day one, building the agent fleet around your workflow
Venture building resources, including design, engineering, growth, and fundraising support from day one
Investor and advisor network across fintech and early-stage capital markets
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.
Clients: Bring over your founding client base and win new mid-market clients through your network
Practice: Own quality of work, review standards, and every client relationship as the firm's lead CPA
Product: Work side by side with the technical co-founder, turning your daily workflow into agents and your review corrections into accuracy gains
Licensing: Lead firm registration and CPA licensing across US states
Capital: Lead the seed raise, supported by FutureSight's network and traction
Team: Hire reviewer CPAs and establish the cultural foundation of the firm
Co-Founder Profile
Licensed US CPA with partner or senior manager experience at an accounting firm
An established book of client relationships you can bring into a new firm
Hands-on experimentation with AI tools in your own practice, and conviction that the firm model needs to change
Strong business development track record, winning and retaining clients on the strength of your work
Product mindset, with the curiosity to break down your own workflow and shape how it gets automated
Ability to build an investor narrative and close capital with FutureSight's support
Experience in bookkeeping, tax, and advisory for 1M–20M businesses
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.
FutureSight is committed to diversity, equity, and inclusion. We welcome applicants of all backgrounds and experiences.
- Department
- Studio Validated Co-founding Opportunities
- Location
- Chicago
- Remote status
- Fully Remote
About FutureSight Ventures
FutureSight is an AI venture builder. We build vertical B2B AI software companies from day zero with values-driven, proven founders. We bring the repeatable company-building execution system, the full-stack cofounding team, and the pre-seed capital. You bring the domain expertise, the grit, and the passion to build a world-class, venture-scale business.