The all-in-one learning co-pilot. Backed by Y Combinator.
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.
What they're looking for
- 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
- You are all‑in on your craft. You don’t half‑build things, you hold yourself to outcomes and whole‑ass 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
More about this role
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...
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