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

FutureSight • Chicago, IL

22d • Remote

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, and the manual close and tax prep workflow that consumes senior staff capacity. Crossfoot connects to existing tools like QuickBooks Online, Xero, and Drake to deliver finished work products ready for partner review, without requiring system migration or enterprise-scale implementation.

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.
• Build the referral-led go-to-market motion.
• Partner with the FutureSight product and engineering team to ship V1 and iterate 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

• 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
• Studio resources, including embedded design, engineering, growth, and fundraising support from day one
• Investor and advisor network across logistics, vertical AI, and early-stage capital markets

What This Job Offers

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