GTM Engineer

What We Do

Yesterday's insurance wasn't built for today's risk. We see it in the data and we feel it in the field. Emerging technology can reinvent how risk is priced and managed, faster and smarter, anchored in proven expertise. First-movers will define the next era of commercial risk management, and Shepherd is building it.

Shepherd is a technology-driven Managing General Underwriter (MGU) transforming commercial Property & Casualty insurance for high-hazard industries. Our mission is to make risk frictionless for the builders and operators shaping the physical world, protecting progress from concept through construction and into decades of operation.

We're building the fastest, smartest commercial risk platform, where underwriting expertise, data, and automation work together to deliver:

• Faster decisions
• Smarter, more accurate pricing
• Better risk outcomes

With Shepherd, safety, speed, and quality no longer trade off against one another. They compound. We're not just modernizing insurance products. We're building the risk infrastructure for the next generation of financial services, where technology, underwriting, and partnerships operate in harmony to support the world's most important industries and the progress they make possible.

Our Investors

In March 2026, Shepherd raised a $42M Series B - bringing total funding to over $60M - led by Intact Private Capital, the investment arm of one of the largest insurers in the world. Intact is not only our lead investor but also a carrier partner, a testament to the confidence the incumbent industry has in what we're building. Our investors:

• Intact Private Capital, led our Series B round
• Costanoa Ventures, led our Series A round
• Spark Capital, led our Seed round
• Susa Ventures, lead our Pre-Seed round
• Y Combinator
• And several others

Our Team

We're a team of technologists and insurance enthusiasts, bridging the two worlds together. Check out our About page to learn more.


GTM Engineer

We're hiring an AI-pilled growth marketer to build Shepherd's growth engine for brokers: paid media, account-based marketing, broker lifecycle, and the agentic workflows and automation that connects it all the way through to submissions. Your title will be Marketing Engineer, Brokerage Growth and you'll report to the Head of Marketing.

About the role

Commercial insurance, especially the retail brokerage channel (which is our distribution channel) is a digitally underdeveloped market. The standard B2B growth stack (SEO/SEM, ABM, email marketing, paid ads, funnels, retargeting, intent signals, AI-search visibility...) is not something our audiences are used to seeing, which makes it a huge opportunity for us to take advantage of. Our growth motion should look like an AI company's growth motion: technical, measured, compounding, and far more productive than a traditional marketing team. In this role, you will prove that thesis by introducing a modern, high-growth engine to a market where standard B2B playbooks barely exist.

As our GTM Engineer, you will build and own that stack. You operate like a growth engineer at a frontier AI company, but apply it to commercial insurance: site experimentation, inbound conversion, paid and ABM programs, outbound infrastructure, marketing automation, attribution, GEO/SEO and AI-search entity infrastructure. You might also have some extra magic gifts for content, social, or building tools. You're hands-on in our channels and shipping improvements every week.

What you'll do

• Own paid media & ABM: Run paid programs end-to-end - audience strategy, channel mix, budgets, creative, testing, and performance with a heavy focus on ABM campaigns that turn broker activations into submissions.
• Build outbound and lifecycle infrastructure: Design and implement broker lifecycle journeys, signal-based triggers, intelligent sequences and plays, and all of the orchestration and wiring to get every broker the right touch at the right time and every Shepherd underwriter the intelligence and enablement they need to be in a position to win.
• Improve conversion across the funnel: Build and iterate on landing pages, forms, and website flows to convert traffic from paid, ABM, and organic channels; you'll own experimentation and CRO.
• Stand up GEO / AI search: Implement structured data, schema markup, and entity infrastructure so Shepherd shows up where brokers and insureds search, including AI-native surfaces.
• Implement marketing automation & attribution: Select and wire the stack (MAP, enrichment, tracking), then build dashboards that clearly show what's working, especially for paid and ABM programs.
• Produce performance creative: Turn ideas into performance assets - self-recorded explainers, lightweight product demos, landing pages, and ad creative - and pull in specialists when we need higher-end production.

Increase experimentation velocity: Continuously test audiences, offers, creative, landing pages, and channels, and translate results into clear next steps for the business.

Who you are

• 4+ years blending growth marketing, demand generation, and technical execution at a fast-moving B2B or consumer technology company.
• Extremely AI-pilled - you live in Cursor, Claude Code, or Codex. You are the first amongst your friends and coworkers to have a take on the latest LLM release.
• High agency and hands-on technically: you don't wait for engineering support to ship a new tool or run a data analysis. You bias toward action, ship weekly, and do as well as you possibly can within what you've set out to do. You're comfortable being the one who moves first and figures it out while others are still whiteboarding.
• You are allin on your craft. You don't halfbuild things; you hold yourself to outcomes and wholeass the system end to end so nothing gets in the way of hitting your goals.
• You like big, complex problems. As we scale, you expect the challenges to get more difficult: data gaps, messy funnels, attribution edge cases... and that excites you. You see new, bigger, harder problems as proof the system is working and leveling up.
• Experienced running growth programs at scale and building the attribution needed to prove impact.
• Comfortable turning rough ideas into usable content (scripts, looms, social clips, quick ad creative) and directing designers or video partners to get to final assets.
• Bonus: experience in insurtech, fintech, or vertical SaaS.
• Extra bonus: experience inside an AI-native company and a clear view of what "AI-native growth" looks like in practice.

How we work

Shepherd runs on four values. Here's what each one means in this seat.

• Think big, build big. We exist to protect progress and the industries that rely on it. The work here is aimed at a system that runs on its own, and the roadmap gets sequenced backward from that rather than forward from what's easy.
• Win together. We rise as one. We support each other, raise the bar, and celebrate collective success. As the first PM you set a standard the rest of the team inherits, and the milestones belong to the team rather than to product.
• Cross the aisle. Collaboration wins. We listen deeply, work across boundaries, and prioritize shared success over individual lanes. The best product calls here come from engineers who've sat with underwriters and underwriters who understand where the model breaks, and much of this job is listening closely enough on both sides to make that happen.
• Go get it. We act with urgency, move with confidence, take smart risks, and push forward with intention. Nobody hands you the roadmap, the data, or the meeting invite. You pull the failing runs, book the time with the underwriters, and decide what matters.

Benefits

Premium Healthcare
100% contribution to top-tier health, dental, and vision

Fertility benefits and family building support

Unlimited PTO
Flexibility to take the time off, recharge, and perform

Daily lunches, dinners, and snacks
We work together, and enjoy meals together too

SF, NYC, Dallas-Fort Worth, Chicago and LA Offices

Professional Development
Access to premium coaching, including leadership development

Competitive 401(k) Plan

Dog-friendly office
Plenty of dogs to play with and make friends with in the SF office