Fleet Sales Leader (Director/VP Level)

Who is Cover Whale?

Cover Whale is an InsurTech company that provides commercial insurance to America's independent truck drivers and trucking fleets. We employ data to make our roads safer and look for exceptional humans to help us make our vision a reality. Our ambition is to combine our passion for improving safety with leading expertise in data science and industry-leading AI/ML/FL practices to not only identify good drivers but also make our drivers and the roads they travel safer. We realize that the commercial trucking industry is the backbone of the American supply chain; here at Cover Whale, our goal is to drive progress in the trucking industry by providing innovative, dynamic insurance solutions that open new horizons of possibilities to drivers, fleet owners, and everyone in between.

Founded in 2019, Cover Whale recently closed a $27.5M Series A funding round with Morgan Stanley Expansion Capital and is continuing to scale and expand its business.  We were also acknowledged in Forbes as one of America's Best Startup Employers 2023 (forbes.com). For more information, please visit www.coverwhale.com. 

Join us in the mission!

The Role:

Cover Whale is a market-leading MGA focused on commercial trucking insurance for individual and small fleets, and it was built from the ground up to transform commercial auto insurance with technology at its core. You will be responsible for replicating this success for larger fleets, in support of our continuing mission to deliver the industry’s leading trucking insurance experience.

Please note: This is a hybrid/on-site (3-4x/week). For the qualified candidate, remote is possible.

Responsibilities:

• Strategic Leadership: Lead and manage the fleet business within commercial trucking insurance, focusing on fleet business growth and expansion across the country.
• Business Development: Cultivate and maintain strong relationships with both retail and wholesale brokers, leveraging these connections to grow a book of business up to $20 million in the first year, and create new selling and servicing interactions leading to increased sales and retention.
• Program Management: Oversee trucking fleet distribution, logistics, and program/binder management, ensuring alignment with company objectives and maximizing profitability.
• Team Management: Work hand-in-hand with underwriting, customer service, and claims teams, fostering a collaborative and results-driven environment.
• Sales: Drive the submission process with a focus on generating and closing new business, aligning with the company’s strategic initiatives of delivering market-leading loss ratios.
• Marketing: Develop, in conjunction with the Chief Revenue Officer and the marketing team, a unique brand and message around Cover Whale’s Fleet offering
• Technology Integration: Promote and implement technology-driven solutions that enhance underwriting efficiency and effectiveness, as well as enhance product market fit, contributing to the broader goals of Cover Whale.
• Market Analysis: Monitor market trends, competitor activities, and regulatory changes in the trucking insurance industry, adjusting strategies as needed to maintain a competitive edge.
• Reporting: Regularly report on key performance metrics, business growth, and team performance to the Chief of Revenue and the executive leadership team, ensuring transparency and alignment with organizational goals.
• Managed experiences: Focus on improving the experience and interaction with your distribution partners and customers. Especially during the proposal and closing process.

Requirements

• BA / BS Degree preferred or equivalent combination of education and experience.
• At least 5+ years' of relevant experience in Commercial Fleet Insurance is a must.

Must-Have Skills/Abilities:

• Industry Expertise: Deep understanding of the trucking insurance market, particularly in wholesale operations.
• Relationship Management: Proven ability to build and maintain strong relationships with wholesale and retail brokers, with a demonstrated track record of growing and managing a significant book of business.
• Leadership & Team Management: Ability to provide strategic and tactical leadership to talented cross-functional teams.
• Business Acumen: Strong strategic thinking skills, with the ability to identify and capitalize on market opportunities to grow the business.
• Sales-Driven Mindset: A producer profile with a focus on getting submission flow and new business generation, rather than traditional underwriting.  However, the regulator to this sales-driven mindset is creating a portfolio of highly profitable businesses. 
• Technological Savvy: Underst