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

WithCoverage risk advisors connecting with clients at an industry event

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

Laura W.

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: 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: I steward our most significant CPG and manufacturing accounts, negotiating directly with carriers to secure terms that are both competitive and structurally sound.
Different here: My focus extends beyond placement into strategic counsel, guiding clients through Business Continuity Planning and Product Recall Risk Mitigation reviews.
Where automation helps: I draw on our benchmarking data and core workflows to deliver outcomes that are efficient, cost-effective, and defensible.
Why this role: I came from insurtech and have worked with upper middle market clients, but wanted to go deeper into that complexity, building solutions firsthand to meet exposures that rarely fit a standard mold.

Typical week: Building tailored insurance programs for General Contractors, Trade Contractors, and Developers covering the project risks that off-the-shelf forms miss.
Different here: When a client requires something that a carrier or traditional broker doesn't offer, I can sit down with our product team and build the toolkit to handle it.
Where automation helps: Subcontractor COI tracking is where many contractors fall short and end up retaining risk. Our proprietary compliance tool handles the collection, chasing, and expiration flags across thousands of certs, so a missing endorsement gets caught before it shows up in a claim, not after.
Why this role: Post-MBA I wanted to build a client base, not inherit one. I've grown the construction practice here from an idea into a real presence in the construction and risk ecosystem.

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.