risk advisory / withcoverage

Spend your time on risk management.

AI agents own the repetitive work around onboarding, policy checks, COIs, and billing. More of your time goes to client strategy, carrier conversations, and program design.

See open roles Meet the advisors

The WithCoverage risk advisory team at their conference booth

the difference

A different job.

At a traditional brokerage, every step of the workflow needs a person, and the software is whatever the vendor shipped. Here, agents run the workflows. With the power of AI, you and a team of engineers help build your vision.

a traditional brokerage

who does the work

Client onboardingyou
Contract reviewyou, line by line
Certificates & endorsementsan assistant, then you
Policy checkingwhoever has time
Billing follow-upyou, after hours
Client strategywhatever's left of the week

when you ask for a better tool

“Can we flag COIs before they expire?”
Forwarded to the vendor's request portal.
Ticket #4,182 · queued
No reply.

You execute the workflow.

withcoverage

who does the work

Client onboardingagents
Contract reviewagents
Certificates & endorsementsagents
Policy checkingagents
Billing follow-upagents
Client strategyyour whole week

when you ask for a better tool

“Can we flag COIs before they expire?”
An engineer pulls up a chair the same day.
You test the first version together that week.
Shipped to every desk.

You own the workflow — and help build the company.

the work

Work on complex insurance programs. Let AI handle the templated renewals.

Most of the work is commercial risk advisory: understanding the business, building the program, negotiating with carriers, and deciding when a policy is not the right answer. Sometimes the right strategy is a simple contract change. Often, it's a fully redesigned insurance program.

01
Loss-sensitive programs
Large deductibles and retention structures for clients ready to take risk back onto their own balance sheet.
02
Alternative risk transfer
Captives and fronted programs when the traditional market is too expensive, too narrow, or too slow.
03
Multinational programs
Coordinated placements across borders, admitted and non-admitted, with local paper where it's required.
04
Emerging technology
Businesses, products, and platforms that do not fit standard forms. We build coverage around how the business actually operates.

carrier network

Work with the carriers clients need.

Direct appointments and wholesale relationships across admitted, E&S, and specialty carriers.

spotlights

Our team and vision for the future.

risk advisory

Wil

Typical week: Working on hard to place risks in our Emerging Tech Practice. From new financial markets to robotics, we have our bases covered.
Different here: Our clients are building their businesses for the future, and we are too. Our clients understand that and lean in to collaborate.
Where automation helps: I leverage automation to cover blindspots in my insurance placements. Tying coverage to unique exposure profiles.
Why this role: I started my career as an underwriter, built a brokerage, and knew WithCoverage's strategy was correct.

Typical week: Manage our largest clients in our CPG and manufacturing vertical.
Different here: I spend time on strategic business conversations like Business Continuity Planning and Product Recall Risk Mitigation Reviews.
Where automation helps: Leverage our benchmarking and key workflows to provide an efficient and cost effective outcome to our clients.
Why this role: I've worked in insurtech, but wanted to push my boundaries by working with upper middle market clients.

Typical week: Bring our construction clients from a legacy or no risk management system, to a modern administrative infrastructure.
Different here: I can quickly build technology with our product team to bring risk management solutions to life.
Where automation helps: Automated COI checking enables my clients to seamlessly manage a large portfolio of subcontractor COI requirements.
Why this role: Post MBA I wanted to be a builder. I've been able to build the construction practice here into a real force in the construction + risk ecosystem.

Typical week: I work directly alongside our Risk Advisory Team to support them across all critical and strategic risk management analysis.
Different here: I come from the Corporate side where I worked directly with Insurance Brokers. Here, I put my Corporate Risk Management hat on to drive strategic value back to our clients.
Where automation helps: I've seen WithCoverage solve complex data problems in a very short timeframe that ultimately will enable our Risk Team to scale.
Why this role: It was clear to me that a shift needed to happen in the insurance brokerage industry. I wanted to be on the forefront of that change.

Typical week: Our clients are some of the most ambitious hospitality professionals in the industry, so generally helping them continue building their portfolio.
Different here: I've been given a level of autonomy and ownership that I didn't have at a large insurance brokerage.
Where automation helps: With so many locations across our portfolios, adding, removing, and checking coverage is critical in my workflows.
Why this role: I wanted to make an impact at a fast growing business. I'm able to do so at WithCoverage.

leadership

Built by insurance and product operators.

Myles Hilliard
Co-founder
Started as a Property & Casualty underwriter at Markel, then advised Vouch's largest clients. Myles built the advisory practice around underwriting discipline.
JD Ross
Co-founder
Co-founded Opendoor and took it from inception through IPO. JD brings company-building and product experience to the operating model behind the advisory team.

verticals

Expertise in specific industries.

We build industry-specific programs where the risk profile, contracts, and carrier appetite are well understood.

Manufacturing & CPG
From plant floor to shelf.
Emerging Technology
Software, fintech, and AI companies.
Hospitality & Retail
Restaurants, retail, and venues.
Construction & Industrials
Projects, trades, and wrap-ups.
Real Estate
Owners, operators, and developers.
Private Equity
Funds, portfolios, and transactions.
Your industry
If your expertise is in another industry segment, we want to hear your thesis.

life here

Carrier events, offsites, and time together.

Carrier events & team outings
Industry conferences, sporting events, dinners, and the occasional show. Relationships still matter in placement.
Company offsites
The company gets together a few times a year to review the work, make decisions, and spend time away from the desk.
Experienced advisors, operators, and builders
The desk is small by design. We hire people who can handle complex accounts, work directly with product, and improve how the desk operates.