Head of Sales

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About the client

Series A InsurTech building modern software that integrates with carrier ecosystems and delivers high-UX digital experiences and workflow analytics. Strong early traction with Tier 1 and Tier 2 carriers and a product roadmap ready to scale.

The brief

Be the first sales leader and build the go to market engine. Partner closely with the founder to transition from founder-led sales to a repeatable, team-based motion. Own enterprise acquisition, create the playbook, hire the team, and deliver predictable ARR growth with Tier 1 and Tier 2 carriers.

What you will do

• Design the GTM strategy including ICP and segmentation, value propositions by buyer, territories, coverage model, and quota design
• Build the sales motion from the ground up: MEDDICC or similar qualification, stage definitions, mutual action plans, executive deal reviews
• Close complex enterprise deals with Tier 1 and Tier 2 carriers, navigating security, procurement, legal, and multi-stakeholder evaluations
• Hire and develop the initial team across AEs, SDRs, and Solutions; set enablement, playbooks, and weekly operating cadence
• Establish pipeline generation with the founder and marketing: ABM campaigns, events, partners, and outbound programs
• Create pricing and packaging with Product and Finance; define ROI narratives and value engineering artifacts
• Stand up RevOps discipline in Salesforce or HubSpot with accurate forecasting, funnel metrics, and capacity models
• Build alliance and partner motions with core system vendors, SIs, and data partners; drive co-sell where relevant
• Capture field feedback to inform roadmap priorities, integrations, and UX requirements

What you will bring

• Eight or more years selling enterprise software into insurance with a focus on Tier 1 and Tier 2 carriers
• Proven record of closing complex, multi-stakeholder deals and running white-glove evaluations and pilots
• Experience standing up or scaling a sales function at an early-stage company and moving beyond founder-led sales
• Credibility with carrier executives across IT, data, underwriting, and operations; fluency in integrations and security standards
• Process-driven operator with command of territory planning, pipeline math, forecasting, and compensation design
• Clear communicator with strong executive presence and collaborative mindset

Seniority level

• Director

Employment type

• Full-time

Job function

• Insurance

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