Director of Marketing

Build the insurance behind the physical world.

The world is building data centers, energy projects, hospitals, schools, and critical infrastructure. Every one of those projects needs insurance to move forward. Yet the process of getting that insurance still depends on scattered documents, manual work, and weeks of back-and-forth.

Shepherd is rebuilding commercial insurance with software, data, AI, and deep underwriting expertise. We started in construction and energy, where understanding the specifics of a project matters and better decisions have consequences far beyond a screen.

We develop insurance products, decide which risks to insure and how to price them, and partner with established insurers to back the coverage. We own the platform our team uses to turn complex submissions into coverage for the builders and operators shaping the world around us.

Real problems. Real ownership.

Our engineers, designers, underwriters, CX, and actuaries build together. The problems span turning messy documents into reliable data, making pricing more precise, and designing AI agents that can take on increasingly complex underwriting work.

The ambition is a platform where experts spend more time on judgment and relationships, supported by software that handles the work around them. Join us to build systems whose decisions help real projects get built.

630+ customers / $500B+ insured project value

Capital to build. Partners to grow with.

$67M total funding / $42M Series B in March 2026

Shepherd is backed by Intact Private Capital, Costanoa Ventures, Spark Capital, Susa Ventures, and Y Combinator. In March 2026, we announced a $42M Series B led by Intact Private Capital, bringing our total funding to $67M.

Intact is also a capacity partner. Alongside its investment, Intact works with Shepherd to bring insurance products to market. That relationship connects our platform and underwriting expertise with the resources of a global insurer.

A bigger opportunity ahead

We are investing in new insurance products, our underwriting team, and the path toward autonomous underwriting. For the people joining Shepherd, that means the chance to shape both the technology and the business it makes possible.

Our backing brings together investors who build technology companies and partners who understand insurance. We are building a company that earns the confidence of both.

As Director of Marketing, you will own how Shepherd reaches and engages commercial insurance brokers, both online and in person. Brokers are our distribution channel, and marketing in commercial insurance has historically been limited. We think there's an opportunity to do things differently.

You'll build our brand, develop content that brokers actually want to engage with, and run events that bring the right people together. You'll work closely with underwriting, business development, and leadership to make sure our marketing programs are reaching the right brokers and ultimately driving more submissions.

This is a hands-on role. You'll set the strategy, run programs yourself, experiment with new ideas, and build the team as we grow.

• Build our events program, from smaller broker dinners and roundtables to roadshows and activations at major industry conferences.

• Work with underwriting and business development to identify the right brokers, offices, and markets to target.

• Create repeatable event playbooks that our teams can run across different regions, with clear follow-up and measurement.

• Come up with new ways to bring brokers together and give them a reason to spend time with Shepherd.

• Develop campaigns that get the right brokers to start working with Shepherd and deepen engagement with existing broker relationships.

• Own our content strategy, working with underwriters and other experts to create useful, relevant content for brokers.

• Test digital and offline channels—including email, LinkedIn, direct mail, industry partnerships, and trade publications—to find effective ways to reach priority broker audiences.

• Measure which programs drive first and repeat submissions, and scale what works.

• Build Shepherd's brand in the commercial insurance market, particularly among the brokerages and producers we want to work with.

• Develop creative campaigns that help us stand out from traditional carriers and MGAs.

• Own how Shepherd shows up across our events, content, campaigns, and other marketing channels.

• Find new ways to get Shepherd in front of the right audience, beyond the standard insurance marketing playbook.

• Work with revenue operations and analytics to measure the impact of our programs, from broker engagement to first submission and repeat submissions.

• Own marketing priorities, budgets, and reporting. Know what's working, what's not, and where we should invest more.

• Hire, coach, and grow the marketing team, and manage the agencies and vendors behind our programs.

You're a marketing leader who wants to build something from the ground up. You've run successful events, built brands, and developed content that gets people to pay attention. You understand how marketing can support a relationship-driven business, and you can point to programs you've built and the results they produced.

You're creative, but you're also an operator. You like coming up with ideas, and you care just as much about getting them done. You're excited by the opportunity to do your best work in an industry where there's still a lot of room to try something new.

• 8+ years in B2B marketing, including experience owning programs or leading teams at a high-growth company.

• A track record of building and running field marketing programs, including proprietary events, conferences, and other in-person activations.

• Experience building campaigns across digital and offline channels, with strong content skills and measurable commercial results.

• Good brand instincts. You know what makes a company stand out, and you've helped build a brand that people recognize and trust.

• Experience marketing to a professional audience, particularly in a business where relationships matter.

• A data-driven approach. You set goals, measure results, and change course when something isn't working.

• Creativity, hustle, and strong execution. You come up with ideas, do the work to bring them to life, and aren't afraid to try something that hasn't been done before.

• AI-native working habits. You use AI tools to move faster, produce content, and find better ways to run programs.

• Experience in insurance, insurtech, fintech, construction tech, or another B2B industry is a plus, but not required.

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. Come set a standard the rest of the team inherits.

• 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.

🏥 Premium Healthcare
100% contribution to health, dental, and vision

🥕 Fertility benefits and family building support

🏖️ Flexible 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