Understory · 1 day ago
Head of Sales (Insurance)
United States
Full-time
Remote
Lead/Staff, Director/Executive
2+ years expUnderstory is a leading provider of insurance solutions built for the era of climate change. As Director of Sales, you will lead a high-performing sales team, refine go-to-market strategies, and establish systems to enhance broker and client relationships while driving new business and deepening existing partnerships.
AnalyticsArtificial Intelligence (AI)Big DataInsurTech
Hiring Manager
Mandi McCarthy
Responsibilities
Leading, mentoring, and developing a small sales team, fostering a culture of accountability, growth, and client-first service
Driving new business sales efforts, including pipeline development, prospecting, and closing deals, while ensuring alignment with company goals
Overseeing the end-to-end client journey, from first interaction through onboarding, adoption, and renewal
Partnering with product and underwriting teams to deliver solutions that meet client needs and expand revenue opportunities
Building scalable systems, reporting frameworks, and success metrics to measure and improve both sales performance and client outcomes
Developing playbooks for prospecting, onboarding, engagement, and retention that balance high-touch service with operational efficiency
Proactively engaging clients and prospects through executive meetings, performance reporting, and solution design tailored to their goals
Acting as an escalation point for complex client or sales issues, balancing urgency with diplomacy to maintain strong relationships
Qualification
Required
Have a minimum of 2+ years of leadership experience managing sales teams in an INSURANCE environment
Have prior experience in the insurance or insurtech sectors and understand how these clients measure success. Preference towards individuals with P&C or reinsurance experience
Have a proven record of winning new business while ensuring long-term adoption, expansion, and retention of client accounts
Have a demonstrated track record of meeting or exceeding quotas and other established sales KPI's year over year
Excel at rolling up your sleeves while setting direction for your team
Possess outstanding interpersonal and communication skills, capable of building trust and credibility with prospects, clients, and internal stakeholders alike
Demonstrate flexibility and adaptability in dynamic, evolving industries, with a track record of creating order and systems out of complexity
Are proactive, solutions-oriented, and thrive on problem-solving while juggling multiple priorities
Have familiarity with CRM platforms (Salesforce or similar), sales enablement, and customer success tools
If local to Madison, you are open to working a Hybrid work schedule in our offices. Remote candidates welcome elsewhere
40-50% travel required
Benefits
Full-time benefits package
Equity package
Company
Understory
Understory is an insurance company that develops smart weather station micro-grids.
11-50 employees
Funding
Current Stage
Early StageTotal Funding
$57.84MKey Investors
Prelude Ventures,True VenturesTrue Ventures4490 Ventures
2024-06-05Series A· $15M
2023-06-06Series Unknown· $13.13M
2020-05-22Series B· $7.5M
Leadership Team
Alex Kubicek
Chief Executive Officer and Co-founder
Bryan Dow
Co-founder
Recent News
globallegalchronicle.com
2025-09-26
2025-09-17
Company data provided by crunchbase