Co-Founder & CEO - AI Benefits & InsureTech
About The Position
FutureSight is seeking an experienced and visionary Founding CEO to lead the launch of a new AI data infrastructure venture serving the $20B+ employee benefits ecosystem across brokers, MGAs, and mid-market employers. Today, brokers and HR teams struggle to make data-driven decisions because benefits data is often locked in carrier portals, PDFs, and spreadsheets, leading to opaque renewals, manual reporting, and poor cost control. Our venture is building an AI-powered data platform that automatically extracts and standardizes benefits data from carriers and brokers, producing instant renewal models, benchmarking insights, and compliance-ready dashboards. The result: faster renewals, clearer cost transparency, and smarter plan design. FutureSight is a venture studio that co-creates and invests in B2B SaaS and Vertical AI startups alongside exceptional entrepreneurs. We give founders an unfair advantage — pairing hands-on studio support with early capital, thereby reducing risk and increasing the odds of success by 10x. We’re led by a cross-functional team of builders and investors. Kevin Nguyen and Alan Smith lead venture design and product strategy. Prathna Ramesh applies her experience as a venture investor with capital strategy in every new business. Dennis Ensing mentors our ventures with operational and strategic expertise, Krista LaRiviere brings years of entrepreneurial and marketing experience as a multi-time exited founder, and Anupama Joshi drives founder excellence. John Carbrey (San Francisco), a successful software entrepreneur and people leader, adds deep insight into scaling startups from 0 to 1, having built and exited multiple prior SaaS ventures.
Requirements
- Founder-level drive — You’re motivated to co-found a new venture as the CEO. With or without us, this is your calling.
- Startup scrappiness — You know what you’re signing up for. You’re familiar with the scrappiness of owning something from start to finish.
- Previous founding experience — You have co-founded a product company or B2B SaaS venture or have been at a venture-backed company.
- Risk appetite and capacity
- GTM chops — Proven success in B2B SaaS sales, marketing, and customer engagement.
- Fundraising fluency — Able to craft investor narratives and close capital; well-networked in fintech and early-stage communities.
- People leadership — Magnet for top talent; coach and culture carrier.
- Industry experience — Background in employee benefits, brokerage, or insurtech / HR data products.
Responsibilities
- Win customers — Run pilots, shape pricing, and validate retention + expansion.
- Build the product — Work with FutureSight’s product/engineering pod to launch V1.
- Raise capital — Lead the seed round with our initial investment.
- Build your team — Hire your founding team and set the cultural foundation.
Benefits
- Validated problem — You will enter a venture with a proven market need and strong momentum toward building and scaling.
- Studio bench strength — Designers, engineers, growth marketers, and fundraising pros are embedded from Day 1.
- Capital commitment — Initial pre-seed funding for early hires and building the MVP with potential for follow-on funding, and access to our investor and advisor network.
- Daily active engagement with our team to: launch initial product, achieve initial market traction and prepare for seed fundraise.
- Full P/L ownership of the new entity.
- A significant equity stake in the business.
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What This Job Offers
Job Type
Full-time
Career Level
Executive
Education Level
No Education Listed
