Guidewire
Director of Competitive Intelligence
2850 S Delaware St, San Mateo, CA 94403
Full-time · $185k–$324k (as posted)
First seen by offpeak October 4, 2026
See your drive time Apply on Guidewire's site
Summary
About GuidewireGuidewire is the platform P&C insurers trust to run, differentiate, and grow their business. As we deepen our investments in AI and expand our market leadership, competitive clarity has never mattered more. This role sits at the center of that story, with real influence over how Guidewire shows up in the market.
Role Overview
We’re looking for a Director of Competitive Intelligence to build and run a high-impact CI function that keeps our field sharp, our positioning credible, and our executives well-informed.
You will own Guidewire’s competitive intelligence program end to end: from market monitoring and win/loss analysis to battlecards, executive briefings, and sales enablement. You’ll manage a small team and work closely with the rest of Product Marketing, Sales, Product Management, Strategy, and GTM leadership to ensure competitive insight actually reaches the people who need it, in a form they can use.
On any given week, you might be:
Synthesizing a competitor’s AI or cloud announcement into a clear POV for the field
Running a regional win/loss debrief and turning patterns into enablement content
Briefing the CRO and CPO on a landscape shift ahead of a strategic planning session
Helping a PMM sharpen positioning and objection-handling against a specific rival
Job Description
What You’ll Do
Build and lead the competitive intelligence program
Design and execute a company-wide CI program, establishing core processes for competitor monitoring, trend tracking, and insight surfacing using dynamic, AI-augmented CI tools.
Create field-ready enablement content (battlecards, playbooks, value narratives) tailored by persona/segment, and partner with Sales Enablement to embed this content into training and coaching to help the field win competitive deals faster.
Lead the structured win/loss program to capture deal data, analyze winning/losing patterns, and translate those findings into concrete, actionable insights and visible performance dashboards for GTM and Product leadership.
Partner with Product/Strategy to inform the roadmap, anticipate market shifts (AI, cloud, etc.), provide clear POVs on competitor strategies/capabilities, and contribute to executive and board-level strategic narratives.
Coach and prioritize work for a small CI/PMM team, acting as a player-coach on critical deals and evangelizing ethical, high-quality CI best practices across the company.
What We’re Looking For
10+ years of B2B software experience in competitive intelligence (CI), product marketing (PMM), strategy, or related fields.
Proven ability to build and scale CI programs, creating field-ready enablement content like battlecards and objection handlers.
Ability to work at multiple altitudes, synthesizing macro market trends for board-level narratives while also conducting deep competitor analysis on specific deals.
Strong executive communication skills for briefing C-level leaders and defending a clear point of view under pressure.
Preferred experience in complex enterprise software markets, with an understanding of multi-stakeholder buying cycles.
Familiarity with modern CI tools and workflows (e.g., Crayon, Klue) and AI-assisted signal collection.
Strong analytical skills, comfortable with both qualitative (interviews) and quantitative data (win/loss stats, pipeline metrics).
What Makes This Role Interesting
Market inflection point: AI, cloud, and core modernization are fundamentally changing how P&C insurers run their business and choose technology partners — your work directly shapes how Guidewire competes in this new reality.
High visibility and impact: You’ll be a key partner to senior GTM and Product leaders, with a direct line of sight from your insights to roadmap decisions, win rates, and strategic narrative.
True cross-functional seat: You’ll collaborate with Product Marketing, Sales, Product, Strategy and more - connecting dots that few others can see.
Opportunity to modernize CI with AI: You’ll have the mandate to evolve Guidewire’s CI practice from static documents to a modern, AI-augmented system of real-time competitive signals, battlecards, and win/loss insight that our field actually lives in every day.
If you’re excited by the idea of shaping how a market-leading platform competes in an AI-first era, and you love turning messy external signals into crisp, actionable guidance, we’d love to talk.
The US base salary range for this full-time position is $185,000 - $324,000. 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.
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.
Guidewire is proud to be a disability inclusive employer. We are committed to providing individualized accommodations and support to candidates for any part of our hiring process. If you think you may need disability-related accommodations, please email EmployAbility at accommodations-gw@employ-ability.org.uk, our disability partner, or schedule a call with an EmployAbility expert (calendar booking slot) for a confidential conversation.