Co-Founder & CEO – AI Benefits & InsureTech

FutureSight; Boston (MA); On-site; USD 180,000 - 280,000; Full time

Benefits offered by this job

Significant equity stake

Job summary

FutureSight is seeking an experienced Founding CEO to launch an AI data infrastructure venture serving the $20B+ employee benefits ecosystem across brokers, MGAs, and mid-market employers. You will lead pilots, shape pricing, and drive the seed round to fund growth.

This full-time role offers significant equity and the opportunity to build the company from the ground up, recruit a founding team, and set a compelling culture and strategy.

Qualifications

• Founder-level drive to co-found and lead a new venture.
• Startup scrappiness and end-to-end product building capability.
• Founding experience in a product company or B2B SaaS.
• GTM, sales, and customer engagement capabilities.
• Fundraising fluency with investor storytelling.
• People leadership and culture-building abilities.

Responsibilities

• Win customers — Run pilots, shape pricing, and validate retention + expansion.
• Build the product — Collaborate with product/engineering to launch V1.
• Raise capital — Lead the seed round with initial investment.
• Build your team — Hire founding staff and set cultural foundations.

Skills

Founder-level drive

Startup scrappiness

GTM chops

Fundraising fluency

People leadership

Industry experience

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.