Job Description

Say hello to Hagerty

Hagerty is a company built by drivers for drivers. We put our members at the center of everything we do, and are dedicated to making it easier and more enjoyable for enthusiasts to drive and celebrate the machines they love. We’re proud to be the world’s largest insurer of collectible and enthusiast vehicles and are home to the Hagerty Drivers Club, the world’s largest car club. Our Marketplace business presents live and digital sales across the U.S. and Europe, we host a number of driving events and concours, and our award-winning automotive journalists produce the most popular car magazine globally, alongside internationally awarded videos. We’re committed to Never Stop DrivingReady to get in the driver’s seat? Join us! 

As Director of Corporate Development, you will lead strategic transactions, including mergers and acquisitions (M&A), investments, divestitures and partnerships. This role requires a strong background in investment banking, corporate finance, and strategic analysis. The ideal candidate will possess exceptional financial modeling skills, transaction experience, and the ability to collaborate across executive and functional teams to execute high-impact deals that support long-term enterprise growth.

What you’ll do

M&A and Strategic Investments

• Lead and support strategic initiatives across the full breadth of Hagerty’s businesses, including insurance, live and digital marketplace, data and analytics, membership, media and events.
• Manage the end-to-end deal lifecycle including target sourcing, valuation, due diligence, negotiation, and integration.
• Proactively source opportunities by attending relevant industry conferences, events, and networking forums, and by maintaining active relationships with founders, executives, investment banks, investors, and intermediaries.
• Develop and maintain a centralized deal and prospects tracker to systematically capture, organize, and assess all evaluated opportunities, ensuring continuity, institutional knowledge, and disciplined follow-up over time.
• Create comprehensive financial models, valuation analyses (DCF, precedent transactions, comparables), and scenario assessments to guide decision-making.
• Prepare and present investment cases.
• Evaluate and prioritize acquisition targets, strategic partnerships, and joint ventures.
• Negotiate term sheets and definitive agreements in collaboration with legal and finance teams.
• Partner with executive leadership and business unit heads to assess strategic fit and synergy potential.
• Collaborate with functional and operational teams to ensure successful integration of acquisitions.
• Define KPIs and track performance against strategic and financial objectives.
• Drive accountability for synergy realization and performance metrics.

Financial and Market Analysis

• Conduct market intelligence and competitive landscape assessments to identify emerging trends and disruptive opportunities.
• Support strategic planning processes with data-driven insights and financial forecasts.
• Work closely with Strategy, Investments, Treasury and Capital Markets teams to evaluate strategic capital decisions and optimize return on investment.

This might describe you

• Proven experience in M&A, Private Equity, Private Credit, or Corporate Development, including at least 2 years in Investment Banking.
• Track record in executing private transactions from origination through integration.
• Very strong quantitative and analytical skills in Excel, including proven ability to build complex models from scratch.
• Experience negotiating and structuring transaction terms.
• Exceptional analytical, communication, and negotiation skills.
• Bachelor’s degree in Finance, Economics, Accounting, or a related field.
• company mission and core values, demonstrating integrity and ethical decision-making.

Over and above

• Experience in private equity, private credit, or venture capital.
• Experience in the insurance industry.
• Familiarity with S&P Capital IQ.

Other things to note

• This position is open to U.S. remote work. However, team members who reside within 20 miles of the Traverse City headquarters will follow a hybrid schedule, working from the office three days per week.
• 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.

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@hagerty.com for compensation, comprehensive benefits and the perks that set us apart. 

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.

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