Business Operations Director - Bridgeport - Hagerty Insurance

Description

Business Operations Director

As the Business Operations Director, you will serve as the head of operations for Hagerty's Digital Marketplace. You will lead and grow a passionate team, ensure the health and scalability of the marketplace, and drive operational efficiencies that fuel business growth. This role requires expertise in dual-sided marketplaces, strong operational and execution skills, and the ability to partner across the organization to deliver strategic initiatives and exceptional customer outcomes.

Ready to get in the driver's seat? Join us What You'll Do

• Lead Strategic Operations: Own operational execution, core business planning, operating cadences, and cross-functional alignment to achieve growth and efficiency goals.
• Drive Insights & Analytics: Monitor performance, identify gaps, and implement solutions using data analysis (SQL, Tableau, Excel). Translate complex insights into clear, actionable recommendations.
• Optimize Marketplace Performance: Improve go-to-market and operational processes, enhance customer experience, and ensure reliable execution across the ecosystem. Balance the supply and demand required to scale a dual-sided marketplace.
• Support Strategic Growth: Evaluate new opportunities, including processes, partnerships, and expansion initiatives. Lead sophisticated business analyses, modeling, and experimentation to inform decisions.
• Collaborate & Influence: Partner with Product, Engineering, Marketing, and other stakeholders to shape strategy and execution. Deliver polished, data-backed presentations to influence executives and drive adoption of recommendations.
• Build, Scale, & Lead Teams: Recruit, develop, and inspire a high-performing operations team, fostering a culture of accountability, innovation, and continuous improvement.

This might describe you

• Owner Mentality: Scrappy, low ego, high horsepower, with a bias toward action and positive change over status quo. Possess high emotional intelligence, a strong "get things done" attitude, and the ability to identify and act on opportunities that accelerate the business forward.
• Product and Systems Mindset: Strong operator who partners deeply with product and engineering, thinking analytically and strategically to improve customer experience, efficiency, and growth across all aspects of the business.
• Data-Driven and Detail-Oriented: Able to move seamlessly between high-level strategy and hands-on execution, using analytics to spot opportunities and guide decisions.
• Strategic & Resilient Operator: Comfortable driving both strategy and execution, not just managing, but making things happen. Thrive in fast-moving, high-autonomy environments with a startup pace and enterprise-level stability. Solves problems from first principles. Excited to solve problems in innovative ways, and resists "this is how it's always been done" thinking. Unafraid of ambiguity, rapid change, thinks learning is exciting, and thrives in ambiguous, startup environments.
• Strong & Clear Communicator: Executive presence with the ability to inspire teams, influence cross-functional partners, and represent Hagerty externally. Communication skills that allow for effective partnership and influence with others at all levels within the organization. Ability to have coach, grow, and when necessary, have difficult conversations with team members.
• Leadership Experience: Demonstrated success in building, scaling, or transforming marketplace operations or verticals. Ability to
• Customer Obsessed: Quickly identifies consumer pain points, leads with the consumer front of mind, and builds a go-to-market strategy to enhance our consumer experience. Ability to balance the needs of both buyers and sellers in a complex dual-sided marketplace.

Qualifications

• 10+ years of experience succeeding in high-performance cultures (whether in tech, operations, strategy, consulting, banking, startups, or a related experience).
• 3+ years leading teams and working directly with executive stakeholders.
• Bachelor's degree required; MBA or Master's degree preferred.
• Strong analytical toolkit: advanced Excel, SQL, Tableau (Python/R a plus).
• Proven ability to translate data into actionable insights and business outcomes.
• Experience in e-commerce, marketplaces, and/or automotive industries strongly preferred.
• Excellent communication and presentation skills with the ability to take complex, ambiguous topics and turn them into compelling narratives for different audiences.
• Demonstrated success as an experienced operator launching, scaling, and/or transforming a marketplace vertical or operational team to drive impactful results.

Other things to note

• This position can be worked remotely within the United States.
• May require travel for quarterly events.
• Familiarity with public company requirements, including Sarbanes Oxley and key regulations, if applicable. For SOX compliant roles, responsible for designing, executing, and documenting internal controls where they have been identified as owners to prevent errors in financial reporting, processes, and business operations. Including attestation to the completeness, accuracy, and compliance of all financial reporting data, where applicable.

Say hello to Hagerty

Hagerty is an automotive enthusiast brand and the world's largest membership organization. Along with being a best-in-class provider of specialty insurance for enthusiasts, Hagerty is also home to the Hagerty Drivers Foundation, Hagerty Drivers Club, Marketplace and so much more. Committed to saving driving for future generations, each and every thing Hagerty does is dedicated to the love of the automobile.

Hagerty is a rapidly growing company that values a winning culture. We provide meaningful work for and invest in every single team member.

At Hagerty, we share the road. We are an inclusive automotive community where all are welcomed, valued and belong regardless of race, gender, age, or car preference. We are united by our shared passion for driving, our commitment to preserve car culture for future generations and our desire to make a positive impact in the world.

If you reside in the following jurisdictions: Illinois, Colorado, California, District of Columbia, Hawaii, Maryland, Minnesota, Nevada, New York, or Jersey City, New Jersey, Cincinnati or Toledo, Ohio, Rhode Island, Washington, British Columbia, Canada please email recruiting@ for compensation, comprehensive benefits and the perks that set us apart.

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EEO/AA

If you like wild growth and working with happy, enthusiastic over-achievers, you'll enjoy your career with us