Sales Director (Insurance)

Understory, Inc.•Madison, WI

2d•Hybrid

About The Position

Have you consistently inspired and led teams to deliver exceptional client outcomes, building long-term partnerships, winning new business, and driving measurable results? Do you thrive in fast-paced, client-centric environments where leadership, strategy, and execution intersect? If the answer is yes, we invite you to elevate your career with us at Understory. As Director of Sales at Understory, you’ll ensure our clients receive a best-in-class experience from their very first interaction with our team through long-term renewal. You’ll lead a small but high-performing sales team, refine go-to-market strategy, and establish the systems and processes that scale strong broker and client relationships across our portfolio. Your leadership will be equally focused on acquiring new business and deepening existing partnerships, positioning Understory as a trusted, long-term partner. In our collaborative, fast-paced environment, you will be surrounded by a team with deep expertise in weather and climate, insurance, and technology. Your leadership and management will be instrumental in shaping how we deliver value to clients and will directly influence our long-term success.

Requirements

Have a minimum of 2+ years of leadership experience managing sales teams in a B2B 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 OR if remote, you are open to occassional travel to Madison.

Nice To Haves

Preference towards individuals with P&C or reinsurance experience.

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.