Applied AI Engineer

About QuoteWell

We started as a vertical SaaS company in insurance. We grew into operating our own wholesale brokerage and a programs group. Through that, we've lived the operational reality of applying AI in insurance — what works in production, what breaks, what compounds. We've just closed fresh funding to scale this operating model to retail insurance agencies across the country.

Our CEO, Joey Bouchard, built and ran applied AI teams at Palantir. We bring that technical rigor together with years of hands-on insurance operations experience to help agencies deploy AI that works in the real world. (Why insurance is worth this attention.)

Why this role exists

Brokerage execution runs on heroics. Service quality depends on who owns the account, how overloaded they are, and what they happen to remember at the right moment. A submission gets marketed broadly, or it doesn't. A renewal gets the same rigor as new business, or it doesn't. A missing detail gets chased, or it stalls.

We don't think that's inevitable. Brokerage execution can be made systematic: software, automation, and AI carrying disciplined follow-through alongside human experts, inside clear bounds, in a regulated environment.

The hard part isn't the model call. It's governability — making AI accountable enough to trust with real deal flow. Who is the AI acting for? What is it allowed to do? What happens when it's wrong? In a regulated industry, those aren't side questions. They're the engineering problem.

We've been answering them inside our own wholesale brokerage for years. That's where we test whether the model actually produces more reliable, scalable, and consistent service. If it doesn't work for us, it doesn't deserve to be packaged for the market. Now we're packaging it.

The role

Applied AI Engineers sit at the point where Terminal, our platform, meets the messy reality of a customer's agency. You own the outcome at the customer. You also own the signal back to the rest of the company.

A typical month: you're embedded at a retail agency, working alongside their operators. You're identifying the workflows where heroics break down — submissions, renewals, follow-up, the work that today depends on someone's memory — and you're building governed AI execution into those workflows on Terminal. You're calibrating where humans stay (judgment, relationships, accountability) and where the system carries the standard (follow-through, coordination, attention).

The hardest and most interesting part: making it trustworthy. How AI decisions get reviewed, attributed, and defended. That work is what determines whether any of this can actually live in production.

Then you bring it all back. Engineering, Product, and Design need to know what generalizes and what doesn't, so the platform compounds across every customer instead of fragmenting into one-offs. You're the conduit.

What you'll do

• Embed at a retail agency and own customer-side execution end to end

• Build governed AI workflows on Terminal — integrating with AMS, carrier portals, email, and the systems an agency actually runs on

• Identify which parts of an agency's operation can be made system-governed without losing the judgment that has to stay with people

• Design the review, attribution, and override patterns that let a regulated business trust the system

• Carry field signal back to Engineering, Product, and Design so the platform scales rather than splinters

• Represent QuoteWell with customers — scope, troubleshoot, and reason about problems out loud, in their conference room

• Travel to customer sites ~25% of the time

What we're looking for

• 1-5 years shipping production software (Python and/or TypeScript a plus)

• Strong engineering foundation — CS degree typical, talented dropouts welcome

• Hands-on experience with modern AI application patterns, or the aptitude and hunger to get there fast

• Someone we can trust in front of a customer: troubleshoot, scope, and reason out loud, in the room

• Genuine appetite to learn an industry deeply. Insurance is a financial supply chain puzzle, and we expect you to want to understand it

• Genuine hustle. The kind of person who walks into Monday with a working prototype of something they spotted on Friday

• Willingness to travel
  

What you get

• A real production model to build on, not a slide deck. Our wholesale brokerage is the proof point — you're scaling something that already works.

• Direct mentorship from Joey, who built and ran applied AI at Palantir before this.

• A leadership trajectory. Hire #1 or #2 on Recon, with a clear path to Applied AI Lead and beyond as we scale.

• An industry that matters. Insurance is one of the largest financial markets in the world and one of the least systematized.

These first few roles set the cultural tone for everything that comes after. If you want to understand what this role actually is, what it isn't, and what it likely means for your career — apply and reach out.

What we offer our full-time employees

• Competitive salaries + equity in the company

• Medical, Dental, and Vision healthcare benefits + FSA and HSA options

• Flexible vacation policy to recharge and live life

• Paid membership to One Medical for employees, spouses / domestic partners, and dependents

• Company-sponsored 401K plan (Roth & Traditional)

• Paid parental leave, generous family forming benefits and up to $5,000 of reimbursements through Carrot

• Up to $1,000 in home office reimbursements to build a productive space to work remotely

• An opportunity to work on solutions that are redefining the future of commercial insurance

• A culture driven by a focus on impact, a shared growth mindset, empowered individuals, and integrity