Director of Sales & Customer Success (Insurance)

Understory, Inc.Madison, WI, US

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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 and Customer Success 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 and customer success 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.

Your main role responsibilities will include :

Leading, mentoring, and developing a small sales and customer success 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. You’re exactly the professional we’re looking for if you :

REQUIRED : Have a minimum of 3+ years of leadership experience managing sales teams in a B2B environment AND a minimum of 12 years of total of sales and / or CS experience. REQUIRED : Have prior experience in the insurance or insurtech sectors and understand how these clients measure success.

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 ocassional travel to Madison.

Compensation includes :

Base salary commensurate with experience + variable compensation package Full-time benefits package Equity package About Understory Understory is a leading provider of insurance solutions built for the era of climate change.

The company's global network of Dot weather stations powers the world's most sophisticated weather risk model.

By combining mutualized, optimized risk structures with precision weather technology and modeling, Understory develops affordable, stable property insurance solutions.

Traditional insurance is no longer fit for purpose.

Natural catastrophes driven by the volatility of climate change are increasing rates and restricting coverage.

Insurance and reinsurance companies are pulling out and leaving 76% of global assets unprotected.

Transformation is inevitable, and it's coming to the global insurance market.

Understory cracked the code, and our approach is the only way to close this gap.

Comprising a compact yet fiercely dedicated & passionate remote team, Understory is a mission-centric, results-driven start-up that thrives on relentless adaptability and resilience.

We cherish accountability and push the limits at breakneck speeds, always backed by the unwavering support of our colleagues.

To sustain our drive, we place significant emphasis on work-life harmony, nurturing our families, and fostering our communities.

Understory, headquartered in Madison, Wisconsin, is poised to rewrite the story of insurance.

To embark on this exciting journey with us, visit www.understoryweather.com .

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Director Of Sales • Madison, WI, US