The AI foundry for the $5 trillion American employee benefits safety net.

We combine twenty years of enterprise experience with AI-native innovation. We aren't just building software; we are building the intelligence that finally makes employee benefits understandable, accessible, and personal.

From the founders who built the enterprise platforms used by 28 Million Employees covered by the industry’s largest insurance carriers, and over 1 Million Employers. We spent two decades scaling the industry's giants; now, we’re building the AI tools they (and we) always dreamed of.

Artificial Intellegence

Meet Benny.

AI that actually knows your benefits.

General AI knows “the world," but it doesn’t know your company. Benny is different. He is grounded in your specific employer document libraries. He doesn't guess; he knows.

  • Grounded in Truth: Answers are derived from your company’s actual benefit documents.
  • Contextual Intelligence: Provides accurate, link-backed answers that consumer chatbots cannot.
Products

The product ecosystem.

SwellSpace

The AI-Native Document Library.

Turn static Docs and PDFs into a dynamic, intelligent knowledge base.

Benny

Your HR and Benefits AI Assistant.

Built on top of all of your HR and Benefits documents stored in SwellSpace, Benny answers employee, dependant, candidates, and retirees’ questions 24/7 and grounded in your company’s information. Benny also builds your benefit sites, analyzes and helps improve your documents, and becomes a key member of your benefits team.

We’ll let you know!

Product research and development.

As an AI and software foundry, we are researchers at heart. We are always tinkering with new ideas and observing problems in the employee benefits world that badly need solving.

The Engine

SwellSpace

A high-performance document repository designed specifically for semantic understanding. It is the foundation that allows AI assistants and agents to navigate complex insurance language with precision.

Visit SwellSpace
The Interface

Benny

The conversational face of modern benefits. Benny helps insurance carriers, employer HR teams, and the many companies inside the benefits ecosystem, set up communication sites and answers direct employee questions 24/7, reducing frustration at the point of key financial decisions.

More about Benny
In our pocket

SwellChat

We did a soft launch of our 3Together lab during the pandemic. We tinkered with a secure video communications platform that connects HR departments, insurance carriers, and brokers with employees to discuss sensitive private information. Leading up to market launch, we decided to put SwellChat in our pocket for future use. We have some ideas of how it might be valuable underneath Benny and future AI assistants and agents and the people they interact with.

Story

The arc of innovation.

We aren’t outsiders looking to “disrupt" an industry we don’t understand. We built the digital architecture that the industry relies on today. Our founders spent over twenty years scaling platforms that reached more than 28 million employees. We saw firsthand where the system works—and where its complexity fails the very people it’s meant to protect.

In 2020, we returned to our roots to start 3Together. We moved away from the traditional SaaS of the past to create an AI Foundry—a lab where we can build the "Intelligence Layer" the industry has been missing.

Jessica Brewer
Cofounder, CEO, and President

LinkedIn

With 25+ years in the technology sector, Jessica specializes in building high-impact software solutions that solve complex business challenges. Before co-founding 3Together, she spent nearly 13 years as Senior VP of Engineering and Global Service at Benefitfocus, leading the platform's growth and technical evolution.

Beyond her executive work, Jessica is deeply committed to community leadership, serving as Board Chair for the South Carolina Aquarium and Charleston Women in Tech, and sitting on the boards of CORE SC and Charleston Digital Corridor Foundation.

Jessica Brewer

Cofounder, CEO, and President
Greg Monn
Cofounder and CTO

LinkedIn

Greg brings deep expertise in enterprise software engineering, most recently as VP of Engineering at Orange Bees. As the second full-time hire at Benefitfocus, he was instrumental in building their market-leading eEnrollment and eBilling applications serving over 20 million people, leading teams in enterprise architecture, performance management, and platform development.

Greg holds an MS in Computer Engineering from Clemson University with a focus in Parallel Systems Architecture and Hardware Acceleration, and a BS in Computer Engineering with a minor in Mathematics, also from Clemson.

Greg Monn

Cofounder and CTO
Jeff Oldham
Chief Growth Officer

LinkedIn

Jeff has spent 25+ years building ecosystems in the employee benefits market, working with employers, health plans, carriers, benefit technology companies, PEOs, and brokers. His experience includes 12 years in National Accounts at Prudential and Unum, 12 years as an executive at Benefitfocus, and 5 years as a consultant specializing in FinTech, Digital Health, and InsurTech.

Named by Employee Benefits Advisor as one of "30 Benefit Thought Leaders to Know" and featured in CNBC, Forbes, and Employee Benefits News, Jeff holds a BA from Texas A&M University and an MA from The University of Essex.

Jeff Oldham

Chief Growth Officer
Shawn Jenkins
Chairman and Head of Product

Shawn co-founded Benefitfocus in 2000 in Mount Pleasant, South Carolina, and served as its CEO for nearly two decades. Under his leadership, the company went public in 2013 and grew to serve more than 28 million employees across the country's largest insurance carriers and over one million employers, reaching $250 million in annual revenue and a valuation exceeding $1.5 billion.

After stepping back from Benefitfocus, Shawn returned to the employee benefits space with a focus on what AI-native software could accomplish that traditional SaaS never could. He co-founded 3Together as a high-intensity innovation lab and serves as its Chairman and Head of Product.

Beyond his business career, Shawn donated $25 million to fund the construction of the MUSC Shawn Jenkins Children's Hospital in Charleston, which opened in 2020. He remains deeply involved with the hospital and is committed to directing the success of 3Together toward funding pediatric medical research worldwide.

Shawn Jenkins

Chairman and Head of Product
Mission

Innovation with purpose.

We believe that technological success is a platform for human progress. Our co-founder and lead investor, Shawn Jenkins, is the primary benefactor of the MUSC Shawn Jenkins Children’s Hospital in Charleston, SC.

Shawn’s involvement with the children’s hospital reflects a deep-seated commitment: that the same spirit of research and development we use to solve AI and software problems can be used to solve the world's most difficult pediatric illnesses. While 3Together is a commercial laboratory, its success fuels Shawn’s personal mission of funding pediatric medical research and supporting the scientists working toward tomorrow’s breakthroughs. His intent is to use the majority of his 3Together ownership to fund pediatric medical research and care.

Careers

Solve high-stakes problems.

We are looking for elite engineers, designers, and project leaders who want to build real-world, high-scale intelligence.

  • The Work: LLM orchestration, RAG (Retrieval-Augmented Generation), AI Agent building, and HIPAA-compliant data security.
  • The Culture: We operate as a high-intensity innovation lab—small, elite teams with “founder energy."
  • Code with a Conscience: Your work helps protect the American safety net and contributes to a cycle of success that funds pediatric medical breakthroughs.
Careers

Fill out the form or contact us directly at careers@3together.us.

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