Co-Founder & CEO — AI-Native Accounting Roll-Up

Job summary

Set Ledgerline’s strategy and lead deal sourcing, valuation, structuring, and closing for acquisitions and equity partnerships with accounting practices. Lead fundraising, recruit the founding team, and work with FutureSight to transform acquired firms using AI and measure improvements in capacity and margins.

Job details

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 new 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.

What you’ll do

Set Ledgerline’s strategy and lead deal sourcing, valuation, structuring, and closing for acquisitions and equity partnerships with accounting practices. Lead fundraising, recruit the founding team, and work with FutureSight to transform acquired firms using AI and measure improvements in capacity and margins.

Requirements

Candidates should have experience in M&A, corporate development, or private equity, with a track record sourcing, structuring, and closing deals with owner-led businesses. They should also bring post-deal integration or transformation experience, the ability to build trust and lead teams, and fundraising fluency; accounting or financial-services experience is a plus but not required.

Benefits

• Founder Equity
• Pre-Seed Capital
• Venture-Building Resources
• Design, Engineering, Growth, and Fundraising Support
• Investor and Advisor Network

Listed skills

• Fundraising · Preferred
• Business development · Preferred
• Team Leadership · Preferred
• Change Management · Preferred
• Accounting · Preferred

Other relevant skills

Identified from the job description. Confirm important requirements above.

• Mergers and Acquisitions
• Corporate Development
• Private Equity
• Deal Sourcing
• Deal Structuring
• Valuation
• Post-Deal Integration
• Operational Transformation
• Fundraising
• Investor Relations
• Strategic Planning
• Business Development
• Team Leadership
• Talent Recruitment
• Change Management
• Accounting

Job areas

• Management & Leadership
• Finance & Accounting
• Technology
• Sales
• Consulting

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