The Opportunity FutureSight is seeking a Co-Founder & CEO to lead Ledgerline, an AI-native accounting roll-up. This is a co-founder partnership with meaningful founder equity, not a salaried executive role. Ledgerline acquires and partners with accounting practices across the US and Canada, rebuilding each one to run AI-native. For every firm, Ledgerline embeds a small technical team that learns the close, tax, and advisory workflows end to end, then builds a fleet of AI agents around what the firm already does well. With AI, a firm can deliver accounting faster, cheaper, and more accurately to small businesses that have always treated clean books as a luxury. The people stay. Agents take the routine work, and staff move into advisory and client work where accountability and judgment matter most. Every agent built compounds into a reusable platform across a growing network of firms. Market Context There are roughly 10,000 US and Canadian firms in Ledgerline's target band, and the profession is aging out faster than it can replace itself: 57% of multi-owner US firms have no written succession plan, 44% of solo practitioners expect to retire within five years, and current CPA exam candidates dropped from 42,626 to 28,082 in a single year. The model is already proven. 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 MVP development, with potential for follow-on funding
• Venture building resources, including embedded 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 direction of the venture and lead its execution.
• Strategy: Define the target firm profile, deal thesis, and value creation playbook
• Deal Sourcing: Build the funnel from the ground up,



identifying practice owners and running outreach through to signed deals
• Deal Structuring: Lead valuation and terms across both paths, full acquisitions and equity partnerships, including navigating CPA ownership rules
• Transformation: Partner with the embedded FutureSight team to take each firm AI-native and document the capacity and margin gains
• Capital: Lead the seed raise and deal financing, supported by FutureSight's network
• Team: Recruit and lead the founding team, and establish the cultural foundation of the company Co-Founder Profile
• M&A;, corporate development, or private equity experience, ideally in professional services or owner-operated businesses
• Track record sourcing, structuring, and closing deals with founder
- or owner-led companies
• Experience leading post-deal integration or operational transformation
• Ability to earn the trust of practice owners and their teams through a major operational change
• Fundraising fluency, with the ability to develop investor narratives and close capital
• Proven ability to attract, develop, and retain top talent
• Exposure to accounting or financial services is a strong plus; an accounting background is not required

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.

📌 Co-Founder & CEO — AI-Native Accounting Roll-Up (Toronto)
🏢 FutureSight
📍 Toronto