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

FutureSight • Chicago, IL

21d

About The Position

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. Crossfoot is agentic accounting for small-to-mid CPA firms, addressing structural accountant shortages, client intake limitations due to production headcount, and the significant time senior staff capacity is consumed by manual close and tax prep workflows. Crossfoot integrates with existing firm tools like QuickBooks Online, Xero, and Drake to deliver finished work products ready for partner review, eliminating the need for system migration or enterprise-scale implementation. The market context highlights a critical need due to significant professional losses in the accounting sector, firms capping client intake by staff availability, and the growing importance of advisory services. Early AI adopters in accounting are already seeing substantial revenue gains per employee, indicating a compounding gap between firms that adopt new technologies and those that do not. The target market is large and underserved, with an estimated total addressable market of $1.5B+ across over 87,000 US accounting firms, and a focused beachhead SAM of $400M+ for small and mid-sized firms. FutureSight is a venture studio that partners with entrepreneurs to build software companies from inception to exit, providing a team of experienced founders, operators, and designers.

Requirements

• Previous founding experience at a venture-backed company.
• Demonstrated success in B2B AI or B2B SaaS go-to-market, including consultative, relationship-driven sales and customer engagement.
• Fundraising fluency, with the ability to develop investor narratives and close capital.
• Proven ability to attract, develop, and retain top talent.
• Clear-eyed understanding of the risks and demands of co-founding a venture-backed company.
• Deep accounting domain expertise, with hands-on experience managing close processes, tax preparation, workpapers, and client accounting services within CPA firms.

Responsibilities

• Set the venture's direction and lead its execution.
• Refine the Ideal Customer Profile (ICP), size-tiered pricing model, and product positioning.
• Lead pilots with managing partners, CAS leads, and outsourced-accounting/BPO operators at small-to-mid CPA firms.
• Convert pilot customers to paid engagements and build a referral-led go-to-market motion.
• Partner with the FutureSight product and engineering team to ship V1 and iterate based on user feedback.
• Lead the seed raise, supported by FutureSight's network and traction.
• Recruit and lead the founding team.
• Establish the cultural foundation of the company.

Benefits

• Co-founder partnership with meaningful founder equity.
• Pre-seed capital committed by FutureSight for early hires and MVP development.
• Potential for follow-on funding.
• Studio resources, including embedded design, engineering, growth, and fundraising support from day one.
• Access to investor and advisor network across logistics, vertical AI, and early-stage capital markets.
• A true co-creation model in which you operate as CEO with the studio as your partner.

What This Job Offers

• Job Type: Full-time
• Career Level: Executive
• Education Level: No Education Listed