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Job description
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.
As Founding CEO, you will
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
About FutureSight
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.
What We Bring
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
What You Bring
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 - Read more on our post on the Entrepreneurial Risk Profile.
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
What You Can Expect
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
This is a full-time role; we are looking for someone to commit full-time and exclusively to building and owning a new SaaS venture
FutureSight is committed to diversity, equity, and inclusion. We welcome applicants of all backgrounds and experiences.
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Worksite address
chicago, IL, 60290, US
Who can apply
Review the original listing for work authorization, qualifications and employer requirements.