Regional Sales Director

Summary

Ready to Build Something Great? Join Guidewire.
Are you an elite enterprise seller looking for your next mission?
Do you thrive in fast-paced environments where your insight, innovation, grit, and execution unlock massive impact?
Are you ready to help transform an entire industry?

Welcome to Guidewire. We're hiring world-class sales executives to help us lead the digital transformation of the Property & Casualty (P&C) Insurance industry — a sector under pressure, yet ripe with opportunity. Between CAT events, skyrocketing reinsurance costs, increasing litigation, inflation-driven loss costs, and labor challenges, insurers need more than just software — they need a true partner to help them adapt, compete, and thrive. 

We’re looking for a high-performing, strategic Sales Representative to join our team and drive new business and growth within a defined territory. You’ll work with the most forward-thinking insurers in North America — from fast-moving start-ups to billion-dollar mutuals and government organizations — bringing the #1 cloud platform for P&C insurance to life.





Why Guidewire?
Industry Leadership
We’re the recognized leader in P&C insurance software, serving 540+ insurers globally. Our cloud platform is trusted by the most innovative insurers in the world.

Our Mission
We exist to power insurance agility — helping insurers engage, innovate, and grow efficiently.

Our Niche
Deliver value through insightful engagement, compelling business cases, and a tailored buying experience that maximizes outcomes for the customer, Guidewire, and team.

Your Opportunity
Join a fast-growing company with industry momentum, strong values, and a commitment to building something exceptional — together.

Travel: 25% (Post-COVID, customer-facing travel as needed)

Job Description

What You'll Do

• Develop and Execute a Strategic Territory Plan

Prioritize top accounts, identify whitespace, and launch high-impact sales campaigns with precision, creativity, and data-driven insight.

• Manufacture Deals, Not Just Chase Them
  Leverage the Challenger Sales Methodology to shape demand, challenge assumptions, and influence buying criteria.
   

• Own the Business. Lead the Charge.

Act as the CEO and quarterback of your territory. Own the full sales cycle — from prospecting to close — while backed by the industry’s top sales team: Business Development, Solution Advisors, Value Engineers, and Professional Services.

• Compete to Win. Deliver Differentiated Value.

World-class reps don’t just sell — they challenge, educate, and lead. You’ll bring deep industry insight, guide strategic conversations, and differentiate Guidewire with value, outcomes, and trusted relationships. You'll master the competitive landscape, shape demand, and partner with customers to drive real business impact.

• Drive Growth in Existing Accounts
  Partner with Customer Success and Services to expand product footprint, introduce new capabilities, and deepen executive relationships.
   

• Deliver Results
  Meet and exceed financial targets — including revenue, profit, and conversion rates,
   

• Be a Trusted Advisor
  Help insurers navigate cloud adoption, digital claims, core system modernization, and ecosystem integration — positioning Guidewire as a long-term strategic partner.

• Stay Sharp. Drive Value. Expand Markets.

Continuously develop your industry, product, and sales expertise. Share insights to shape strategy, expand market reach, and uncover new opportunities.
 

What We’re Looking For

• What It Takes to Win Every Quarter, Every Year: Endurance, positivity, and relentless improvement in pursuit of excellence.

• 5+ years of core enterprise SaaS software sales experience -  Track record of dominating quota and consistently outperforming peers in high-stakes, competitive environments.

• Deep understanding of the full enterprise sales cycle — experience with complex negotiations, RFPs, long-term deal strategy, modern procurement processes, multiple stakeholders, and LOBs.
   

• Mastery of strategic selling methodologies (e.g., Challenger)
   

• Ability to build and influence relationships at all levels — from tech teams to C-suite
   

• High financial and commercial acumen — able to navigate pricing, ROI, value drivers, and contractual terms with ease