Head of Sales, Insurance at GenLogs in Chicago, IL

GenLogs is a hardware, software, and data company building the next generation of Truck Intelligence™. Our mission is to build unbreakable supply chains in order to make our world safer and stronger. Through a nationwide network of sensors, we help our customers source carriers, eliminate fraud and theft, and provide real-time visibility on every truck in America. By operating at the intersection of edge sensing, computer vision, AI-driven analytics, and large-scale field deployment, GenLogs is transforming how transportation data is captured, secured, and commercialized.

About the GTM Team

The Insurance Go-to-Market team at GenLogs is responsible for bringing our nationwide commercial-vehicle intelligence platform to the Commercial Auto Insurance industry. We work directly with insurers to define problems, scope operational deployments, and scale high-impact programs. As the commercial face of GenLogs, we translate the capabilities of the Trident sensor network and freight intelligence data platform into clear value propositions that strengthen decision-making in underwriting, claims, and ultimately improve the underlying loss ratios of commercial auto insurers. This mission is critical in ensuring that coverage remains affordable and to support a healthy and thriving supply-chain. The team operates with urgency, precision, and deep market understanding, collaborates closely with Product, Engineering, and Data Science to ensure our solutions solve the most important problems in the Insurance ecosystem.

About the role

GenLogs’ Head of Sales, Insurance, will lead our commercial strategy and sales execution as we scale our intelligence platform across Insurance Carriers. This role is responsible for managing our account executives, as well as the entire Insurance sales lifecycle from start to finish, including prospecting, need finding, presenting, solution definition, strategic account planning, deal structure, and managing relationships with prospects and customers driving predictable and sustainable revenue growth.

You must be sales-driven, fast-moving, and have a strong customer focus. You are passionate about creating value for your customers, which ultimately leads to profitable business for both us and them. You know how to identify the right decision makers and influencers, how to listen, and how to ask the right questions. This leadership position reports directly to our Chief Revenue Officer and works closely with marketing, product, and customer success to drive continued success for GenLogs!

What you'll do

Strategy & Leadership

• Help our Chief Revenue Officer build, lead, and retain a world-class go to market organization focused on enterprise sales to Insurance Carriers.
• Establish sales KPIs, compensation plans, quota models, and forecasting processes to drive accountability and scalability.
• Identify new market opportunities, competitive threats, and strategic partnerships within the Insurance technology ecosystem.

Enterprise Sales Execution

• Manage a team of Account Executives driving enterprise deals.
• Oversee execution of a full-funnel complex enterprise sales motion from first contact to closure, including strategic account expansion.
• Drive business growth by cultivating a network of executive level contacts at major Insurers.
• Support deal strategy for high-value and complex enterprise opportunities; Engaging directly with C-suite stakeholders.
• Lead pricing strategy evolution based on market trends, competitive dynamics, and customer value realization.
• Own the global sales target for the insurance GTM vertical

Field Sales, Partnerships & Channel Development

• Represent the company at major industry conferences, association events, customer roundtables, and partner roadshows.
• Work with Marketing to evaluate the ROI of events, sponsorships, and alliance initiatives and make budget recommendations based on measurable impact.
• Champion the company externally as a thought leader.

Customer Lifecycle & Expansion

• Assist with managing revenue models aligned around long-term customer success, renewal, and expansion.
• Partner with Customer Success to ensure smooth onboarding and consistent value realization for enterprise accounts.
• Develop referenceable customers, case studies, and advocacy programs to accelerate sales momentum.

Qualifications

• Sophisticated sales executive with 10+ years of experience selling complex SaaS technology to enterprise customers, in the P&C insurance space, in a closing role, using a consultative approach to determining customer needs.
• Experience managing consultative sales cycles, with 7+ figure deals.
• Strong familiarity with the Commercial P&C Insurance space, including processes, regulations, key stakeholders, and performance KPIs.
• Familiarity and comfort selling across stakeholders at multiple levels in an organization, communicating well with everyone from the business champion to the C-level executive.
• Strong analytical skills, with the ability to develop and run long-term account plans.
• Proven success scaling a revenue organization from early stage through growth preferably from $5M → $30M+ or similar.
• Track record of building and leading high-performing sales teams including hiring, coaching, compensation design, and performance management.
• Comfortable in a startup environment that moves at a fast pace, with a direct, open, and honest culture. You care about getting the best answer, not about being right or wrong.