GTM Engineer

Yesterdays insurance wasnt built for todays 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.

Were 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. Were not just modernizing insurance products. Were building the risk infrastructure for the next generation of financial services where technology underwriting and partnerships operate in harmony to support the worlds most important industries and the progress they make possible.

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 were 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

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

Were hiring an AI-pilled growth marketer to build Shepherds 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 youll report to the Head of Marketing.

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 companys growth motion: technical measured compounding and far more productive than a traditional marketing 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. Youre hands-on in our channels and shipping improvements every week.

What youll 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; youll 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 whats 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.

• 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 dont 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 youve set out to do. Youre comfortable being the one who moves first and figures it out while others are still whiteboarding.

• You are allin on your craft. You dont 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.

Shepherd runs on four values. Heres 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 whats 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 whove 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.

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

Required Experience:

IC