Transportation Sales Leader - Insurance

San Francisco, CA
Who we are: 

KeepTruckin is on a mission to modernize the trucking industry. With the leading fleet management platform, we are bringing trucks online and fundamentally changing the way freight is moved on our roads.

We are a Forbes Cloud 100 company and we’ve been recognized by Glassdoor as a “Best Place to Work” in 2019. We’re on the hunt to find talented individuals to join our growing team.

Located in the city’s South of Market (SOMA) neighborhood, the KeepTruckin headquarters is a walk away from Oracle Park (go Giants!) and Union Square. Our building—built in 1923—has a unique industrial, open feel made comfortable with countless comfy couches and beautiful greenery. When they’re not working, you can find fellow team members playing pool, enjoying the rooftop view, and exploring this historical city.

The Transportation Sales Leader, Insurance supports the sales implementation and team growth, shaping the segment’s strategy with the Director of Insurance BD, Head of SMB and VSB Sales.  The core focus is driving growth (penetration, new business) for both existing and new customers of insurance company-leveraged safety telematics products. This position is located in SF, CA, but we are also open to moving it to our Nashville office.


    • Provides insurance product sales expertise to VSB and SMB sales teams in messaging and selling integrated insurance company partner offerings.
    • Supports Head of SMB and VSB to achieves their annual sales goals managing sales performance against individual and team sales targets through use of coaching, motivation and metrics.
    • Provides direct sales support in outbound telesales campaigns, educating, motivating and leading sales teams to execute selling KeepTruckin subscriptions tied to insurance discount-leveraged products.
    • Identifies client needs and develops custom solutions through KeepTruckin partners.
    • Ensure that sales placements are handled correctly and on time.
    • Develop productive business relationships with key insurance company underwriters, brokers and MGAs.
    • Participate and/or leads special projects that require Sales and Service Center participation.
    • Coordinate activities with other internal units as required to meet customer needs.


    • Emerging leader with transportation insurance sales experience in VSB, SMB or MM accounts.
    • Effective working knowledge of insurance company underwriting, risk management and claims practices & processes.
    • Demonstrates telematics and insurance technical competency, or ability to learn.
    • Proven client facing skills including effective presentations & communications.
    • Attention to detail, ability to multi-task, exceptional organizational skills, ability to make and communicate difficult decisions.
    • Experience in building successful sales teams,  resource deployment and utilization management.
    • Strong interpersonal skills, with the ability to interact effectively at various levels of organization and range of fleet size customers.
    • Successfully operates in a fast-paced driven environment that requires the ability to handle multiple tasks simultaneously.
    • Minimum of 7 years of insurance broker or company experience, with concentration on Trucking and/or Commercial Auto.
    • Proven leadership skills in working with teams and ability to work with clients and to successfully exceed client expectations.
    • Must maintain Property & Casualty insurance broker license.
    • Proficientient in Salesforce or similar CRM system.
As an equal opportunity employer, we are committed to diversity in the workforce. In accordance with applicable law, we prohibit discrimination against any applicant or employee based on any legally recognized basis, including, but not limited to; race, color, religion, sex (including pregnancy, lactation, childbirth or related medical conditions), sexual orientation, gender identity, age (40 and over), national origin or ancestry, physical or mental disability, genetic information (including testing and characteristics), veteran status, uniformed service member status or any other status protected by federal, state or local law.