Senior Account Executive (Insurance)

Understory, Inc.•Madison, WI

About The Position

Are you a proven producer who thrives on opening doors, building strategic partnerships, and driving new revenue in complex, consultative sales environments? Do you have the credibility to engage senior decision makers and the persistence to turn early conversations into long-term, scaled partnerships? If so, we invite you to take on a high-impact role at Understory. As a Strategic Account Executive (or Director, Business Development), you will be responsible for originating and closing new business, while shaping how Understory goes to market. This is not a traditional account executive role — it is a frontline, externally facing position focused on hunting, influencing, and winning. You will play a critical role in expanding Understory’s footprint, bringing our differentiated climate-driven insurance solutions to market, and building the partnerships that will define our growth trajectory.

Requirements

Proven track record of new business generation in insurance, reinsurance, or insurtech — with a history of closing complex, high-value deals.
Deep experience working with brokers, MGAs, or commercial insureds, and a strong existing network you can activate.
Ability to sell consultatively and navigate ambiguous, evolving products and markets.
Demonstrated success building pipeline from scratch and operating in a true “hunter” role.
Strong commercial instincts and comfort structuring deals and influencing underwriting conversations.
Executive presence and the ability to engage senior decision-makers with confidence and credibility.
Highly self-motivated, resilient, and comfortable operating in a fast-paced, high-growth startup environment.
Experience with Salesforce or similar CRM tools, with strong pipeline management discipline.

Nice To Haves

Background in property & casualty or commercial lines insurance strongly preferred.

Responsibilities

Own new business development across brokerage partners, MGAs, and strategic clients — from initial outreach through deal close and early-stage expansion.
Proactively identify and penetrate target accounts, leveraging industry relationships, market insights, and creative outreach strategies.
Build and manage a robust pipeline, consistently driving opportunities forward with urgency and discipline.
Engage senior stakeholders with credibility and a consultative approach.
Position Understory’s differentiated offering by translating complex climate risk and insurance solutions into clear, compelling value propositions.
Lead negotiations and deal structuring, partnering closely with underwriting, product, and leadership teams.
Act as the quarterback internally, ensuring alignment across sales, underwriting, and operations to successfully bring new programs to market.
Stay close to key accounts post-sale, ensuring strong early adoption and identifying expansion opportunities (without owning long-term servicing).
Provide market intelligence and feedback to inform product development, pricing strategy, and go-to-market approach.
Represent Understory externally at industry events, conferences, and key partner meetings.