Co-Founder & CEO - AI Healthcare Revenue Recovery
$50k - $300k per yearFutureSight
The Opportunity
FutureSight is seeking a Co-Founder & CEO to lead Reclaim , an AI-native denial management and revenue recovery venture. This is a co-founder partnership with meaningful founder equity, not a salaried executive role.
We are entering a $16B+ Total Addressable Market with a gaping $ 7.5B–$10B whitespace, targeting the highly underserved mid-market segment. Currently, 30–40% of denied medical claims go uncontested because practices lack the staff and capital to contest them. This systemic failure leaves between $50,000 and $300,000 in legally earned revenue permanently abandoned at each practice every year.
Reclaim AI resolves denied and aged claims end-to-end, embedding outcome-based contingency pricing—meaning practices pay zero upfront, and we only take a cut of the dollars we successfully recover, for our target ideal customer profile (practices with $80K+ in annual recoverable claims).
Market Context
We didn’t just read market reports; we spent weeks interviewing billing managers, practice owners, revenue cycle leaders at health systems, and even digital operations leaders at major insurance companies. The dysfunction we uncovered is staggering, creating a massive opportunity for a disruptor:
- The pain is so severe, practices are building their own tech: The frustration of payer opacity is so deep that medical billers are hiring part-time software engineers to build in-house robotic process automation (RPA) scrapers just to check claim statuses.
- Massive, emotional write-offs: Staff carry immense guilt over these administrative losses. One small-practice assistant admitted, "I feel like we probably had to write off probably close to a million dollars" simply because they couldn't keep up with the manual follow-ups.
- The "Payer-Side Inversion" Opportunity: We discovered that insurance companies are drowning in the exact same claims dysfunction they generate. One major payer we interviewed reported a backlog of 31,000 contested claims that consumed 80% of their staff's operational capacity, forcing emergency hires just to manage the disputes.
- The Competition is Distracted: Well-funded Tier-1 competitors are charging $15K+ upfront licensing fees and fighting over enterprise health systems. The competitive window to capture the mid-market with a contingency-priced autonomous agent is wide open.
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 studio 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 vertical AI 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.
- Strategy — Refine the ICP, pricing model, and product positioning
- Customer Development — Lead pilots with practice owners and revenue cycle leaders, convert them to paid engagements, and build the go-to-market motion
- Product — Partner with the FutureSight product and engineering team to ship V1 and iterate on user feedback
- Capital — Lead the seed raise, supported by FutureSight's network and traction
- Team — Recruit and lead the founding team, and establish the cultural foundation of the company
Co-Founder Profile
- Domain & Workflow Depth: You have direct exposure to healthcare revenue cycle, medical billing, or denial management. You understand the nuanced differences in denial codes, know why administrative denials (like credentialing gaps) are uniquely painful, and intuitively understand the fragmented systems (e.g., Tebra, eClinicalWorks, Availity) that billers are forced to use
- Previous founding experience at a venture-backed company
- Demonstrated success in B2B AI or B2B SaaS go-to-market, including 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
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.
$360k per year
...The Opportunity FutureSight is seeking a Co-Founder & CEO to lead Weli , a B2B WealthTech venture. This is a co-founder partnership with... ...founder equity, not a salaried executive role. Weli is an AI-native operations platform purpose-built for wealth management...SuggestedInternshipWork at office$150k per year
...The Opportunity FutureSight is seeking a Co-Founder & CEO to lead Concordance , an AI-native clinical documentation compliance venture. This is a co-founder partnership with meaningful founder equity, not a salaried executive role. Concordance AI audits 100% of healthcare...SuggestedInternshipManual labor- ...The Opportunity FutureSight is seeking a Co-Founder & CEO to lead Maestro , an AI-native inventory-planning intelligence venture. This is a co-founder partnership with meaningful founder equity, not a salaried executive role. Maestro is an autopilot planning intelligence...SuggestedInternshipImmediate start
- ...The Opportunity FutureSight is seeking a Co-Founder & CEO to lead Closeline , an AI-native mortgage origination venture. This is a co-founder partnership with meaningful founder equity, not a salaried executive role. Closeline is building the AI-native infrastructure...SuggestedInternship
- ...is seeking an experienced, visionary entrepreneur to co-found its next B2B AI venture with us. This is a co-founder partnership with meaningful founder equity, not a... ...A true co-creation model in which you operate as CEO with FutureSight's cross-functional team as your partner...SuggestedFull timeInternship
- ...The Opportunity FutureSight is seeking a Co-Founder & CEO to lead Foundry , an AI-Native Recruiting Agency currently in build at FutureSight. This is a co-founder partnership with meaningful founder equity, not a salaried executive role. Recruiting has run on the...InternshipShift work
- ...The Opportunity FutureSight is seeking a Co-Founder & CEO to lead Omnex , an AI-native operating system for multi-channel ecommerce sellers, currently in build at our studio. This is a co-founder partnership with meaningful founder equity, not a salaried executive role...Internship
- ...Description The Opportunity FutureSight is seeking a Co-Founder & CEO to lead Crossfoot , an AI-native accounting agent platform currently being built at our studio. This is a co-founder partnership with meaningful founder equity, not a salaried executive role. Crossfoot...RemplacementFull timeInternship
- ...The Opportunity FutureSight is seeking a Co-Founder & CEO to lead HawkAI , an enterprise AI venture for US logistics brokerages, carriers, and warehouse operators. This is a co-founder partnership with meaningful founder equity, not a salaried executive role. HawkAI...Internship
$200k per year
...The Opportunity FutureSight is seeking a Co-Founder & CEO to lead LucentAI , an AI-native litigation operations venture in build at FutureSight. This offers meaningful founder equity, not a salary. LucentAI serves as an autopilot for medical-records and discovery...InternshipImmediate start- ...delivery economics, and scalability. The teams that ship credible AI workers into finance-sensitive functions in the next 18 months... ...delivered through the same managed model. The Partnership The CEO co-founder is in place. The customer thesis is validated, design partners...Day shift
- ...delivery economics, and scalability. The teams that ship credible AI workers into trust-sensitive verticals in the next 18 months... ...delivered through the same managed model. The Partnership The CEO co-founder is in place. The customer thesis is validated, design partners...Internship
- ...Opportunity FutureSight is seeking an applied AI builder to co-found and lead the technical direction... ...from the ground up. This is a co-founder partnership with founder-level equity and... ...inception to exit. We are a team of founders, operators and designers with experience...Full timeInternship
- : Co-Founder Opportunity – Growth & Business Development Help Build the Future of Vehicle Ownership and Automotive Service The automotive aftermarket still operates as two largely disconnected worlds. Vehicle owners struggle to maintain a complete record of what has happened...Long term contractPart timeInternship
- ...Executive Assistant & Personal Assistant to the CEO About Dokainish & Company Since 2011... ...~ Prior experience supporting a CEO, founder, or senior executive in a professional services... ...STATUS: This posting is for a new position. AI USAGE: This organization does not use...Full timeWork at officeFlexible hoursShift work
- ...Executive Assistant of President & CEO WELL Health Diagnostic Centres is looking for... ...facilities in Ontario. More than 15,000 Ontario healthcare providers refer their patients to WELL... ...by The Globe and Mail for sustained revenue growth. Responsibilities: • Assist the...Full timeTemporary workInternshipWeekend workAfternoon shift
- ...Default Recovery Officer Mortgage finance company looking for a Default Recovery Officer to work with external and internal stakeholders... ...and ensuring all costs up to date in the system. Order and/or co-ordinate occupancy inspections on properties. Verbal and...Full timeContract workWork at officeFlexible hours
$20 - $25 per hour
...organized and detail-oriented Administrative Clerk to support our Recovery Team on a part-time basis. In this role, you will support... ...identity, or life experience, you are welcome here. We may use AI to support our hiring process. While these tools assist our team,...Hourly payFull timeContract workPart timeInternshipWork at officeRemote workMonday to fridayFlexible hours- ...and highly-organized team member to join our Revenue Operations team. The Revenue Operations... ...Vancouver (Within BC). We offer flexible co-working locations available to Loopers in ON... ...about what you could bring to the table. AI in Recruitment At Loopio, we leverage...Full timeInternshipRemote workWork from homeHome officeFlexible hours
$120k - $160k per year
...What does success look like in this role? The Senior Disaster Recovery Specialist is responsible for developing, implementing, maintaining... ...As part of our hiring process, we may use technology, including AI-based tools, to help summarize and assess applications; these tools...Permanent employmentFull timeFlexible hours$70k - $100k per year
...empowered teams. Combine your passion with purpose and join a culture that is thriving in the face of change. Make an impact with our Recovery & Restructuring team as a Senior Consultant. This diverse team of professionals assists lenders and debtors with managing challenging...Full timeImmediate startRemote workFlexible hours$138.5k - $173k per year
...Role The Manager, Integrated Marketing - Co-Marketing leads DoorDash Canada's co-... ...efficient impact. Have experience using AI tools within your day to day (e.g., Claude,... ...comprehensive benefits and perks including premium healthcare, wellness expense reimbursement, paid...Full timeLocal area- ...role is the strategic thought leader for Revenue Operations at Mortgage Automator. It goes... ...the truth. You'll also be expected to use AI tools to push both the customer experience... ...supporting total well-being, including physical recovery or mental health. Commuter-Friendly...Full timeWork at officeRemote workWork from homeFlexible hours
- ...together and can scope a build, and hold a credible conversation with a founder about their GTM tech stack. You have directed the work of... ...the 8th wonder of the world - compounding growth. How We Use AI in Our Hiring Process: To ensure transparency, we want candidates...Full timeFor contractors
$350k - $400k per year
...first time. We're hiring our first Chief Revenue Officer to own the full revenue lifecycle:... ...organization reporting directly to the CEO: Sales – new-school and new-district... ...of the overall compensation package. AI at Minga At Minga, we believe AI should...Full timeRemote work- ..., so they can focus on what matters most: delivering top-quality service to their customers. We are currently looking for a Field Recovery Agent Responsibilities Conduct round trips to collect and retrieve electric bicycles, mopeds from debtors. Confidently communicate...
$110k - $160k per year
...The Opportunity We are seeking a Data Architect for o ur AI & Data practice team. We are looking for a candidate with strong... ...stakeholders and teams Lead cross-functional projects involving healthcare IT professionals, data scientists, and clinical stakeholders...Long term contractWeekend work- ...integration of enterprise-level platforms within a complex public sector healthcare environment. This role focuses on developing scalable, secure,... ...including RDS multi-zone deployments and disaster recovery Experience with APIs, ETL pipelines, and modern web technologies...Full time
- ...aeronautical engineers who realized that the healthcare system was not exploiting the full... ...Job Description As our first Chief Revenue Officer, you will own the full revenue engine... ...and Partnerships. Reporting directly to the CEO, you will architect and execute a go-to-market...Full timeContract workInternshipPrivate practiceWork at officeWorldwideFlexible hours
$45 - $65 per hour
...creative and technical talent with leading AI research labs. Headquartered in San... ...Summers , and Jack Dorsey . Position: Revenue Cycle Expert Type: Contract... ...asynchronously to improve AI model performance in healthcare revenue cycle evaluations....Hourly payWeekly payFull timeContract workFor contractorsSummer workRemote work
Do you want to receive more vacancies?
Subscribe and receive similar vacancies to Co-Founder & CEO - AI Healthcare Revenue Recovery. Be the first to apply!
- top executive Toronto, ON
- senior executive Toronto, ON
- chief medical officer Toronto, ON
- chief human resources officer Toronto, ON
- direction générale Toronto, ON
- human resources executive Toronto, ON
- chief innovation officer Toronto, ON
- chief wellness officer Toronto, ON
- ceo Toronto, ON
- executive director Toronto, ON
