Forward Deployed Engineer, Growth
New York, NY
About WithCoverage:
WithCoverage replaces the traditional insurance brokerage with AI-supercharged risk management designed for the modern economy.
We partner with hundreds of high-growth, category-defining companies, including GoPuff, Eight Sleep, Bombas, Chomps, and Blank Street Coffee. Our clients span iconic consumer brands, hospitality leaders, GCs, advanced manufacturers, and next-generation defense contractors. They operate in complex risk environments and need a partner that can move at their speed.
Instead of a fragmented, manual brokerage stack, we have built a new category: elite risk advisors operating on top of proprietary technology. Our in-house Agency Management System gives our team and AI agents full visibility into policies, exposures, claims, billing, and commissions. This platform enables deep automation, better decisions, and a fundamentally higher standard of service.
WithCoverage was founded by JD Ross (co-founder of Opendoor) and Max Brenner (Bain, Compound). We have raised over $50M from leading investors including Sequoia, 8VC, Khosla Ventures and Crystal Venture Partners.
Our ambition is not to build a better brokerage. It is to redefine how risk is managed across the economy.
Why Join Us
- Grow Faster – We're scaling quickly, giving you real opportunities to lead, shape strategy, and accelerate your career.
- Work That Matters – We protect the world's most innovative brands: consumer icons, hospitality leaders, next-gen defense contractors, and US manufacturers.
- Redefine an Industry – Insurance is one of the largest, slowest-moving markets. We rewrite the playbook with proprietary technology, automation, and AI.
- Financial Rewards – We hire the best and invest in you. Competitive comp, meaningful equity, and excellent benefits. We believe strongly in internal promotion and lay out a plan for everyone's career growth.
Location: In-office, NYC HQ. This role works daily across Marketing, Sales, Revenue Ops, and client-facing executives, so we've built it to be in-person.
About The Role
We’re looking for a customer-facing engineer to build AI-powered tools and workflows on WithCoverage’s Growth team and help prospective customers put AI to work in their businesses.
You’ll partner closely with Product, which will define and scope much of the work, and own the engineering execution: writing code, connecting systems, testing behavior, and getting working tools into people’s hands. You should be comfortable taking a defined problem and independently making the technical decisions needed to build a practical, reliable solution.
You’ll also be a technical resource our Growth and Sales teams can bring directly into prospect conversations. As an AI-native insurance brokerage, we can offer operators something valuable: access to an engineer who can answer their questions, demonstrate useful approaches, and help them apply AI to their own workflows.
Hands-on building and prospect conversations are both substantial parts of the job. We’re looking for someone who enjoys writing software and can bring that same confidence and clarity to a room of nontechnical operators.
What You'll Do
- Own engineering execution. Partner with Product on defined projects and take responsibility for implementation. Build AI-powered tools, applications, scripts, and integrations; make technical decisions; and own debugging, testing, deployment, and iteration.
- Build AI workflows that work in practice. Connect LLMs, APIs, and business data to solve concrete workflow problems. Evaluate outputs against real examples, handle errors and edge cases, and improve reliability as people use what you build.
- Help Sales secure the next call. Join prospect conversations and email threads to answer technical questions, work through specific problems, and demonstrate useful applications of AI. Help Sales turn that value into a concrete next step: a working session, a tailored demonstration, or a deeper conversation about WithCoverage.
- Teach in plain language. Give nontechnical operators practical advice they can apply to their businesses. Walk them through tools, demonstrate approaches using relevant examples, and help them understand how to use AI effectively and check its work.
- Be the technical expert on the call, and build after it. Understand enough of a prospect’s workflow to give sound technical guidance. When follow-up calls for a working example, build a prototype, script, or lightweight tool using relevant sample data and documents.
- Keep the work useful and maintainable. Document what you build, reuse components where it makes sense, and communicate technical constraints and implementation tradeoffs to Product and Core Engineering.
Who You Are
- 4+ years of technical experience, ideally including time in an AI or analytics practice at a consulting firm (QuantumBlack, BCG X, Bain Vector, Accenture, or similar) or in a forward-deployed / solutions engineering role
- You've built AI-powered things that real people used. Prompt engineering, retrieval, agents, evals. It doesn't need to have been at a massive scale, but it needs to have been real.
- You can explain how an LLM works to someone who has never written code, and they leave feeling capable rather than lectured to. This is the single most important qualification.
- Genuinely strong client instincts. You can read a room, handle a skeptical executive, tell someone their idea won't work without losing them, and know when to stop talking.
- You want to be on calls and in rooms. This is a people-facing job that happens to require an engineer, and roughly half your week looks like that.
For candidates based in the United States, the expected base pay range for this position at the start of employment is $140,000 – $170,000/year + equity on top of it. Actual compensation will vary based on individual factors, including market location, relevant experience, and role scope. In addition to base salary, this role is eligible for variable compensation tied to performance or quota attainment, where applicable. WithCoverage’s Total Rewards package for full-time employees also includes equity participation and comprehensive benefits. If you’re excited about the role but your compensation expectations are outside this range, we’d still love to hear from you; final offers reflect experience, scope, and leveling.
What We Offer:
- Competitive compensation that includes equity
- Comprehensive benefit plans for medical, dental, vision, life, and disability
- Pre-tax accounts (FSA, HSAs, dependent care FSAs, commuter savings)
- Human Interest: 401(k) provider
- Time Off: Flexible time off, sick leave, family and medical leave, and major national holidays
- A curated in-office employee experience, designed to foster community, team connections, and innovation
- Collaborative, transparent, and fun culture
Skills Required
- 4+ years of technical experience
- Experience building AI-powered tools used by real people
- Experience with prompt engineering, retrieval, agents, and evaluations
- Ability to explain how LLMs work to nontechnical audiences
- Strong client instincts and ability to work with skeptical executives
- Comfort with customer-facing conversations and approximately half the week spent on calls or in rooms
- Experience in an AI or analytics consulting practice or a forward-deployed or solutions engineering role
WithCoverage Compensation & Benefits Highlights
The following summarizes recurring compensation and benefits themes identified from responses generated by popular LLMs to common candidate questions about WithCoverage and has not been reviewed or approved by WithCoverage.
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Fair & Transparent Compensation — Pay is considered competitive on paper, with several roles posting explicit salary or OTE ranges. Job materials also indicate equity and variable components are part of the package, signaling upfront clarity on structure.
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Healthcare Strength — Health coverage breadth is emphasized, including medical, dental, vision, life, and disability insurance. These core plans are consistently listed for full-time roles.
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Leave & Time Off Breadth — Time-off provisions include flexible PTO, sick leave, family/medical leave, and major holidays. This breadth suggests multiple pathways to take leave rather than a narrow policy.
WithCoverage Insights
What We Do
The insurance brokerage industry is ready for a new standard: ambitious businesses often overpay for insurance, are inadequately protected, and are left with a non-transparent, disorganized experience. Most businesses don’t have an in-house Risk Management Team. That’s where we come in. WithCoverage provides ambitious businesses with a Modern Risk Management Solution. An expert team and powerful technology – designed to protect you today and as you scale. A few of our clients include: GoPuff, Chomps, Hungryroot, Blank Street, Bombas, Eight Sleep, Bluestone Lane, Salt & Straw, Kitsch, Happy Dad, and Elephante.
