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
   

• Strong executive presence and powerful, persuasive communication skills — written, verbal, and presentation
   

• Passion for growth, collaboration, and impact — hungry to learn, coachable, resilient, and committed to excellence

• Familiarity with the P&C insurance industry, its business model, and digital transformation priorities (preferred)
   

What We Value

• Integrity – Truthful relationships with customers, prospective customers, partners, investors, and each other.

• Rationality – Communicating through clear arguments, building excellent quality products, and making decisions carefully on the basis of factual evidence. 

• Collegiality – Working together as professional equals, with a minimum of hierarchy.

Let’s Build Something That Lasts

Guidewire is more than a software company — we’re a community of builders, thinkers, and problem-solvers who believe in doing things the right way. If you’re ready to stretch yourself, contribute to something meaningful, and be part of a team that’s shaping the future of insurance, we want to hear from you.

Apply today — and bring your best.

The US base salary range for this full-time position is $132,000 - $198,000 . Your base pay will depend on your experience, skills, education, training, and location among other factors. All full-time positions or part-time roles working 30 hours or more a week at Guidewire are eligible for benefits that support their health and well-being including health, dental, and vision insurance, paid time off, and a company sponsored retirement plan. In addition, some roles may be eligible for the annual company bonus plan, commissions, and/or long term incentive awards which are contingent on a variety of factors including, but not limited to, company and employee performance.

Disability Accommodations and Guidewire’s Appeals Process. Guidewire provides accommodations to the hiring process to create a fair opportunity for candidates with disabilities to contend for open positions. Accommodation requests should be directed to [email protected]. If things do not go as hoped, we invite you to use our appeals process. Guidewire promises to independently review any denied accommodation and any decision not to offer you the position. The appeals process is the same in either case. Within five business days of receiving a notice of denial of an accommodation, or receiving a notice of your non-selection for a vacancy, e-mail [email protected] to make an appeal. Guidewire will assign a new decision-maker to review the request and/or hiring decision, who will then notify you in writing of a decision within 10 business days.

About Guidewire

Guidewire is the platform P&C insurers trust to engage, innovate, and grow efficiently. We combine digital, core, analytics, and AI to deliver our platform as a cloud service. More than 540+ insurers in 40 countries, from new ventures to the largest and most complex in the world, run on Guidewire.

As a partner to our customers, we continually evolve to enable their success. We are proud of our unparalleled implementation track record with 1600+ successful projects, supported by the largest R&D team and partner ecosystem in the industry. Our Marketplace provides hundreds of applications that accelerate integration, localization, and innovation.

For more information, please visit www.guidewire.com and follow us on Twitter: @Guidewire_PandC.

Guidewire Software, Inc. is proud to be an equal opportunity and affirmative action employer. We are committed to an inclusive workplace, and believe that a diversity of perspectives, abilities, and cultures is a key to our success. Qualified applicants will receive consideration without regard to race, color, ancestry, religion, sex, national origin, citizenship, marital status, age, sexual orientation, gender identity, gender expression, veteran status, or disability. All offers are contingent upon passing a criminal history and other background checks where it's applicable to the position.