Job Description
Commission-Driven | Remote | Industry-Focused
Carrier Software is seeking a results-oriented Vice President of Sales with deep experience in commercial auto and trucking insurance to lead revenue growth for our underwriting intelligence and risk-analytics platform.
This is a high-visibility, high-impact role for a proven insurance sales professional who understands how carriers, MGAs, and agents evaluate trucking risk—and who has the relationships and credibility to open doors at the decision-maker level.
If you thrive in a hunter role, are motivated by commission upside, and want to sell a product that genuinely improves underwriting accuracy and profitability, this role was built for you.
About Carrier Software
Carrier Software is a trusted provider of commercial transportation data, underwriting analytics, and safety intelligence used by insurance carriers, MGAs, wholesalers, and truck insurance agencies nationwide. Our solutions help underwriters identify risk earlier, price more accurately, and reduce loss ratios by combining insurance data, FMCSA insights, and proprietary analytics.
What You’ll Do
As Vice President of Sales, you will own the full sales lifecycle and serve as a strategic ambassador to the trucking-insurance market:
Develop and execute outbound sales strategies targeting truck insurance agencies, carriers, GAs, MGAs, and fleet insurers
Leverage existing industry relationships to generate qualified opportunities
Identify and engage senior underwriting, product, and executive decision-makers
· Actively shape marketing strategy, messaging, and positioning based on frontline market feedback
· Collaborate with leadership on go-to-market planning, campaigns, and target segments
Conduct high-impact live demonstrations tailored to underwriting and risk teams
Build customized proposals and confidently close new business
Address underwriting, compliance, and data-quality questions with authority
Maintain long-term client relationships and expand account value
Provide direct market feedback to product and development leadership
Represent Carrier Software at industry conferences, trade shows, and events
What We’re Looking For
This role is intentionally senior and industry-specific. Qualified candidates will have:
5+ years of experience selling within commercial auto / truck insurance
Direct knowledge of how carriers and MGAs evaluate trucking risk
A strong network within trucking insurance (agents, MGAs, carriers, or reinsurers)
A proven record of closing B2B deals in relationship-driven environments
Confidence speaking with underwriters, actuaries, and executive leadership
Exceptional presentation, negotiation, and follow-up skills
Self-motivation and comfort working independently in a performance-based role
Familiarity with underwriting analytics, loss runs, safety data, or insurtech (preferred)
Compensation & Why This Role Is Different
Commission-driven compensation with meaningful upside
Opportunity to sell a differentiated product with strong market demand
Direct influence on product roadmap and go-to-market strategy
Fully remote with flexible work structure
Small, agile team where your performance directly impacts company growth
A chance to be an early revenue leader in a growing insurtech platform
Who Should Apply
This role is ideal for:
Senior insurance sales professionals tired of selling commoditized products
Former underwriters or agency producers who moved into sales leadership
Insurance executives looking for equity-like impact without corporate bureaucracy
Relationship-driven sellers who want autonomy, accountability, and upside
Pay: From $40,000.00 per year
Education:
Bachelor's (Required)
Experience:
truck insurance industry: 5 years (Required)
Work Location: Remote
Carrier Software is seeking a results-oriented Vice President of Sales with deep experience in commercial auto and trucking insurance to lead revenue growth for our underwriting intelligence and risk-analytics platform.
This is a high-visibility, high-impact role for a proven insurance sales professional who understands how carriers, MGAs, and agents evaluate trucking risk—and who has the relationships and credibility to open doors at the decision-maker level.
If you thrive in a hunter role, are motivated by commission upside, and want to sell a product that genuinely improves underwriting accuracy and profitability, this role was built for you.
About Carrier Software
Carrier Software is a trusted provider of commercial transportation data, underwriting analytics, and safety intelligence used by insurance carriers, MGAs, wholesalers, and truck insurance agencies nationwide. Our solutions help underwriters identify risk earlier, price more accurately, and reduce loss ratios by combining insurance data, FMCSA insights, and proprietary analytics.
What You’ll Do
As Vice President of Sales, you will own the full sales lifecycle and serve as a strategic ambassador to the trucking-insurance market:
Develop and execute outbound sales strategies targeting truck insurance agencies, carriers, GAs, MGAs, and fleet insurers
Leverage existing industry relationships to generate qualified opportunities
Identify and engage senior underwriting, product, and executive decision-makers
· Actively shape marketing strategy, messaging, and positioning based on frontline market feedback
· Collaborate with leadership on go-to-market planning, campaigns, and target segments
Conduct high-impact live demonstrations tailored to underwriting and risk teams
Build customized proposals and confidently close new business
Address underwriting, compliance, and data-quality questions with authority
Maintain long-term client relationships and expand account value
Provide direct market feedback to product and development leadership
Represent Carrier Software at industry conferences, trade shows, and events
What We’re Looking For
This role is intentionally senior and industry-specific. Qualified candidates will have:
5+ years of experience selling within commercial auto / truck insurance
Direct knowledge of how carriers and MGAs evaluate trucking risk
A strong network within trucking insurance (agents, MGAs, carriers, or reinsurers)
A proven record of closing B2B deals in relationship-driven environments
Confidence speaking with underwriters, actuaries, and executive leadership
Exceptional presentation, negotiation, and follow-up skills
Self-motivation and comfort working independently in a performance-based role
Familiarity with underwriting analytics, loss runs, safety data, or insurtech (preferred)
Compensation & Why This Role Is Different
Commission-driven compensation with meaningful upside
Opportunity to sell a differentiated product with strong market demand
Direct influence on product roadmap and go-to-market strategy
Fully remote with flexible work structure
Small, agile team where your performance directly impacts company growth
A chance to be an early revenue leader in a growing insurtech platform
Who Should Apply
This role is ideal for:
Senior insurance sales professionals tired of selling commoditized products
Former underwriters or agency producers who moved into sales leadership
Insurance executives looking for equity-like impact without corporate bureaucracy
Relationship-driven sellers who want autonomy, accountability, and upside
Pay: From $40,000.00 per year
Education:
Bachelor's (Required)
Experience:
truck insurance industry: 5 years (Required)
Work Location: Remote
💡 Quick Summary
Seeking a career-building opportunity? The Vice President of Sales – Commercial Truck Insurance Technology position is now open for candidates interested in the Work from home Jobs sector. This role in Illinois offers a professional environment and growth potential.
Requirement Snapshot: Candidates should possess basic communication skills, a proactive attitude, and the ability to work in a team. Experience in Work from home Jobs is a plus.
