Who is Cover Whale?
Cover Whale is the nation’s leading commercial trucking insurtech. We enhance road safety by integrating our insurance products with our telematics-based, data-driven driver coaching and safety program, DriveSmart. Our program is proven to save lives while delivering better insurance for our drivers. For more information, please visit www.coverwhale.com.
The Role:
We are rapidly expanding and looking to build a dynamic team of Regional Business Development professionals. The Business Development Associate will report to the Senior Business Development Manager, Deputy Lead, and support strategies to increase premium production in their region. This role involves managing smaller, established partners and newly onboarded partners, ensuring their successful integration and growth. The Associate will also develop strategies for these partner cohorts and provide key insights on their portfolio's makeup during quarterly reviews. If you’re excited by meaningful ownership, strong relationships, and the opportunity to make a real impact, we encourage you to apply. Join us in the mission!
Responsibilities:
- Collaborate with underwriting, marketing, and growth teams to develop, manage, and drive distribution and generate partner premium
- Oversee a portfolio of emerging and lower-volume partners, with accountability for fostering relationships, identifying growth potential, and ensuring consistent performance
- Support Business Development Managers in driving production
- Provide pipeline support by researching target markets, potential partners, and competitive intelligence
- Identify and execute opportunities to further engage with current partners
- Establish, track, and report on KPIs while routinely meeting or exceeding goals
- Assist in the constant improvement of business development, partner management, and onboarding processes
- Drive a positive brand image amongst our current trading partners and prospects with continuous outreach
- Support event and field presence efforts within the assigned region, including preparing partner materials and assisting with logistics for retail-focused engagements
- Monitor partner performance trends and flag opportunities or risks to the Business Development Manager or Leader
- Maintain CRM accuracy, HubSpot, by updating partner interactions, notes, and performance data promptly
- Other duties as assigned
Requirements
Requirements:
- 3+ years in a fast-paced sales role
- Experience in onboarding and guiding new customers to realize and repeat value
- Exceptional interpersonal skills, able to discuss technical and business topics seamlessly
- Strong phone and video skills, maintaining professionalism under pressure
- Experience with disciplined execution of challenging opportunities that lead to results
Desired Qualifications/Skills:
Consultative Sales & Deal Coaching Skills:
- Ability to identify issues and coach agents through the sales funnel by diving into individual submissions and collaborating with partners on opportunities
High-volume outreach and Structured Sales Execution:
- Mastery of multi-channel outreach (calls, email, LinkedIn, and in-person) using repeatable cadences
- Ability to run effective discovery meetings and consistently secure next steps
- Experience moving prospects efficiently from first touch to bind
Preferred Qualifications:
- Bachelor’s degree in Business Administration, or related field
- Have experience in Metabase or similar software to pull, review, and analyze data
Work schedule expectations: The Business Development Associate works closely with teams operating in the Eastern Time zone. Flexibility to align with core Eastern Time business hours is required.
Travel Requirements: This role is primarily in-market/within your region, with occasional travel (approximately 10–15%) required as needed.
Benefits
At Cover Whale, we believe in transparent and equitable compensation practices. The expected base pay for this role has a range of $61,000- $91,000 per year. Final base pay is determined based on several factors, including skills, experience, and geographic location. Base pay is only part of our total compensation package, which also includes:
- Annual discretionary bonus opportunity
- Comprehensive health, dental, and vision insurance
- 401(k) company match up to 4 %
- Generous paid time off and company holidays.
Cover Whale works to maintain the best possible environment for our employees, where individuals can learn and grow with the company. We strive to provide a collaborative environment where each person feels encouraged to contribute to their processes, decisions, planning, and culture.
We are an equal opportunity employer, and all qualified applicants will receive consideration for employment without regard to race, color, religion, sex, national origin, disability status, protected veteran status, or any other characteristic protected by law
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What We Do
Our ambition is to combine our passions for improving safety with industry-leading expertise in data science, along with industry-leading practices in AI/ML/FL to not only identify good drivers but to actually 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. By leveraging technological efficiencies, continuous underwriting, and AI-based telematics, we harness the power of technology to bring the best over to small trucking fleets. We make this often difficult process user-friendly by streamlining everything. What separates Cover Whale from our competitors is our underwriting process. We work quickly and efficiently. Using technology to identify good drivers, we are able to offer lower prices to a subset of individuals who value safety and focus. And the best part is that we are making the roads a safer place with every truck we insure!
