[Hiring] Co-Founder & CEO - AI Benefits & InsureTech @FutureSight

Role 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.

Qualifications

• 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.

Requirements

• 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.

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.

Company Description

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.
• 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.