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.

Brand & Experiences

We’re hiring a resident vibe-making machine to own how Shepherd shows up in the world from conferences and broker dinners to social, executive brand, and the content and comms that tie it together. Your title will be Brand & Experiences and report to the Head of Marketing.

About the role

This role owns Shepherd’s presence across events, brand, content, and social. You design the unique experiences brokers remember, the activations that feel more like great parties than industry conferences, the dinner series brokerage leaders are jealous they didn’t get invited to, and the social and content layer that amplifies Shepherd’s unique point of view in the world of commercial insurance, AI infrastructure, construction, and renewable energy.

Shepherd’s positioning and story are in place; the visual, experiential, and social expression of that story is still catching up. Our brand should feel like a frontier AI company punching above its weight. Our events should feel like parties with a guest list that people are dying to get on. You should be able to tell in 2 seconds from looking at our web, decks, and social properties that they’re from Shepherd (unmistakeable and entirely different from the rest of insurance). This role closes that gap and helps us win the rooms that matter with brokers, insureds, and partners.

Most companies would split this work across brand, events, and social. At Shepherd, you’ll own all three: events that stand out from the crowd, but at the same time connect clearly to our brand system that shows up consistently across every surface, and content and executive social that reinforce the same story while looking like no one else in insurance.

What you’ll do

• Lead event strategy and execution: Own conference and field marketing strategy across industry events, vertical events, brokerage events, and Shepherd-hosted programs. This world is fragmented and disorganized. You will bring clarity to this chaos. Design and execute broker-facing dinners, roundtables, office activations, and one-of-one experiences for key distribution partners.

• Run proprietary Shepherd experiences: Develop and execute Shepherd-specific events and activations that reflect our brand and stand out from traditional carrier programs.

• Own social and executive brand: Manage executive social narratives for our leadership team (especially Justin and Mo) — narrative arcs, posting calendars, prompts, and support on writing, clipping, and publishing. Oversee social and content output across company channels.

• Manage content and creative partners: Lead the contractor and agency stack that produces social, video, blog, and broker-facing nurture content. Drive lightweight production yourself (outlines, scripts, looms, social copy, basic video clipping) to keep momentum between larger shoots.

• Steward the brand system: Apply and evolve Shepherd’s visual and verbal identity across web, decks, broker collateral, event presence, swag, and careers pages. Partner closely with our Marketing Engineer on web experiences.

• Coordinate press and comms: Manage relationships with any PR or comms partners, prioritize opportunities, coordinate spokespeople, and ensure earned coverage reinforces the narrative we’re building.

• Own budgets and vendors: Manage six-figure budget for events and production, negotiate with vendors, and ensure flawless execution on logistics and experience.

Who you are

• 5+ years across some combination of brand, events, field marketing, or experiential marketing in high-growth B2B, consumer, fintech, hospitality, or agency environments.

• You are all‑in on experiences. Proven ownership of large-scale events and experiences or organizing, from strategy and budget through execution and follow-up. You don’t dabble in events or brand; you obsess over the room and every detail. You’re the person people ask about what’s happening when the weekend rolls around. You’d rather do fewer things and do them whole-ass than run a calendar of forgettable programs.

• You have great business sense for the return on your programs + intuition around unquantifiable outcomes: you track who showed up, what changed, what got done afterward, how much GWP we bound as a result, but you’re also making sure to create nights people talk about a year later.

• You lean into bigger, harder problems. As the program grows, you expect more difficulty: multi‑city roadshows, co‑branded anchor events, athlete activations, overlapping audiences… and that’s where you want to be. You’re energized by the complexity of pulling it all together.

• Strong creative taste and sense of brand: you can instantly judge whether work is on-trend, on-brand, high quality, and explain why.

• Comfortable directing designers, photographers, videographers, and content agencies to produce consistent, high-quality output.

• Experience shaping and amplifying executive voices across social and earned channels, either directly or in close partnership with comms/PR.

• AI-native: you use AI tools to accelerate prep, logistics, copy, and content production so you can focus on relationships, decisions, and creative direction. You’re comfortable walking through the fire. Tight timelines, shifting priorities, demanding rooms — you stay composed, keep your standards, and still deliver something you’re proud of. You use AI and modern tools to compress the busywork so you can focus on judgment.

• Comfortable in tools like Figma and modern media/creative tooling; able to do light hands-on work when needed.

• Bonus: maybe you’re a content creator who knows how to bring something special to an industry that doesn’t have the nerve to do things differently. Maybe you’ve run a meme account before or led some truly innovative and different events program in what might be considered a boring industry.

• Extra Bonus: experience in insurance, financial services, or construction-adjacent industries

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