Co-Founder & CEO - AI Benefits & InsureTech
FutureSight
Job Overview
Location
Remote
Employment Type
Full-time
Work Arrangement
Remote
Sector
Information Technology & Software
Experience Level
Executive (12+ years)
About the Company
FutureSight is a dynamic venture studio dedicated to co-creating and investing in innovative B2B SaaS and Vertical AI startups. We partner with exceptional entrepreneurs, providing them with an unparalleled advantage through hands-on studio support and early-stage capital. Our mission is to significantly reduce risk and amplify the probability of startup success.
Our leadership comprises a cross-functional team of experienced builders and investors. We offer a unique investment approach, working closely with a select group of founders each year. The comprehensive resources, coupled with access to extensive advisor and funding networks, empower founders to concentrate on the critical elements needed for rapid market entry and sustained growth.
Job Description
FutureSight is seeking an experienced and visionary Founding CEO to spearhead the launch of a groundbreaking AI data infrastructure venture. This initiative is designed to serve the expansive employee benefits ecosystem, encompassing brokers, MGAs, and mid-market employers.
The current landscape presents a significant challenge, with employee benefits data often fragmented across carrier portals, PDFs, and spreadsheets. This lack of accessibility hinders data-driven decision-making, leading to opaque renewal processes, laborious manual reporting, and difficulties in controlling costs.
Our venture is developing an innovative AI-powered platform engineered to automatically extract and standardize benefits data from various sources. This platform will generate immediate renewal models, provide valuable benchmarking insights, and deliver compliance-ready dashboards, ultimately facilitating faster renewals, enhancing cost transparency, and enabling more intelligent plan design.
As the Founding CEO, your responsibilities will include winning customers through pilot programs, shaping pricing strategies, and validating retention and expansion models. You will collaborate closely with FutureSight’s product and engineering teams to launch the Minimum Viable Product (MVP). Furthermore, you will lead the seed funding round, leveraging our initial investment, and be instrumental in building your founding team and establishing the company's cultural foundation.
To apply for this role, click the Apply button on this page and follow the instructions.
Required Skills
Key Responsibilities
- Win customers by running pilots, shaping pricing, and validating retention and expansion.
- Collaborate with product and engineering teams to launch the Minimum Viable Product (MVP).
- Lead the seed funding round and engage with investors.
- Build the founding team and establish the company's cultural foundation.
- Drive overall business strategy and execution.
Qualifications
- Founder-level drive and a strong desire to co-found a new venture.
- Experience in startup environments, understanding the scrappiness of owning a project from start to finish.
- Previous founding experience in a product company or B2B SaaS venture, or significant experience in a venture-backed company.
- Demonstrated risk appetite and capacity for entrepreneurial challenges.
- Proven success in B2B SaaS sales, marketing, and customer engagement (Go-to-Market chops).
- Fluency in fundraising, including crafting investor narratives and closing capital.
- Strong people leadership skills, with the ability to attract top talent and foster a positive culture.
- Industry experience in employee benefits, brokerage, or insurtech / HR data products.
Benefits & Perks
- Validated problem with a proven market need and strong momentum.
- Access to studio bench strength including designers, engineers, growth marketers, and fundraising professionals from Day 1.
- Initial pre-seed funding for early hires and MVP development.
- Potential for follow-on funding and access to an extensive investor and advisor network.
- Significant equity stake in the business.
- Full P/L ownership of the new entity.
How to Apply
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The employee benefits and insurtech sector is experiencing significant disruption, driven by the need for data-driven decision-making in a complex market. This role demands a leader adept at navigating the $20B+ employee benefits ecosystem, leveraging AI to transform data from disparate sources into actionable insights. You will architect an AI-powered platform to standardize benefits data, enabling faster renewals, enhanced cost transparency, and optimized plan design. Your impact will be measured by customer acquisition, product launch success, capital raising, and team building, directly influencing the company's growth trajectory and market position.
Posted Date
April 5, 2026
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