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About the Role

As Director of Marketing, you will own how Shepherd reaches and engages commercial insurance brokers, both online and in person. You'll build our brand, develop content that brokers actually want to engage with, and run events that bring the right people together. This is a hands-on role where you'll set the strategy, run programs yourself, experiment with new ideas, and build the team as we grow.

Responsibilities

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.
Own our content strategy across LinkedIn, email, newsletters, and other channels where we can reach brokers.
Work with underwriters and other subject matter experts to create content that's useful, interesting, and relevant to our audience.
Build campaigns that keep Shepherd top of mind with brokers, whether they've never worked with us or submit regularly.
Experiment with different formats and channels, measure what works, and double down on the ones that drive engagement.
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.
Hire, coach, and grow the marketing team, and manage the agencies and vendors behind our programs.

Requirements

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.
Strong content marketing experience, including developing content strategies and growing engagement across digital channels.
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.

Skills

B2B marketing
Field marketing
Content marketing
Brand building
Digital marketing
Event management
Data analysis
AI tools

Location

SF
NYC
Dallas-Fort Worth
Chicago
LA

Work Type

Full-time

Experience Level

8+ years

Benefits

Premium Healthcare (100% contribution to health, dental, and vision)
Fertility benefits and family building support
Flexible PTO
Daily lunches, dinners, and snacks
Professional Development (Access to premium coaching, including leadership development)
Competitive 401(k) Plan
Dog-friendly office

About the Company

Build the insurance behind the physical world.
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.
Our engineers, designers, underwriters, 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
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.
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.