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Shepherd is rebuilding commercial insurance with software, data, and AI. The company has raised $67M (including a $42M Series B in March 2026) and insures $500B+ in project value across 630+ customers. They partner with established insurers to provide coverage for critical infrastructure projects in construction, energy, and related sectors.
As Director of Marketing, you will own how Shepherd reaches and engages commercial insurance brokers—the company's primary distribution channel. This is a hands-on, strategic role where you'll build the brand, develop broker-focused content, and run events that drive submissions and engagement.
Key responsibilities:
FIELD MARKETING & EVENTS: Build Shepherd's events program from broker dinners and roundtables to roadshows and industry conference activations. Work with underwriting and business development to identify target brokers, offices, and markets. Create repeatable event playbooks for regional execution with clear measurement and follow-up.
CONTENT & DIGITAL MARKETING: Own content strategy across LinkedIn, email, newsletters, and other channels reaching brokers. Partner with underwriters and subject matter experts to create useful, relevant content. Build campaigns that keep Shepherd top of mind. Experiment with formats and channels, measure engagement, and double down on what works.
BRAND MARKETING: Build Shepherd's brand in the commercial insurance market, particularly among target brokerages. Develop creative campaigns that differentiate from traditional carriers and MGAs. Own Shepherd's presence across events, content, campaigns, and marketing channels. Find new ways to reach the right audience beyond standard insurance marketing playbooks.
MEASUREMENT & TEAM: Work with revenue operations and analytics to measure program impact from broker engagement to first and repeat submissions. Own marketing priorities, budgets, and reporting. Hire, coach, and grow the marketing team; manage agencies and vendors.
You'll work closely with underwriting, business development, and leadership. The role requires both strategic thinking and hands-on execution—you'll set strategy, run programs yourself, experiment with new ideas, and build the team as Shepherd grows.
REQUIREMENTS:
- 8+ years in B2B marketing, including program ownership or team leadership at a high-growth company
- Proven track record building and running field marketing programs (proprietary events, conferences, in-person activations)
- Strong content marketing experience with demonstrated ability to develop strategies and grow digital engagement
- Strong brand instincts and experience building recognized, trusted brands
- Experience marketing to professional audiences in relationship-driven businesses
- Data-driven approach: set goals, measure results, adjust course based on performance
- Creativity, hustle, and strong execution; comfort trying new approaches
- AI-native working habits; use AI tools to move faster and improve program delivery
- Experience in insurance, insurtech, fintech, construction tech, or similar B2B industries is a plus but not required
