Director of Competitive Intelligence

Guidewire Software•San Mateo, CA

1d•$178,000 - $268,000

About The Position

Guidewire 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. 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

Requirements

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.1
Strong executive communication skills for briefing C-level leaders and defending a clear point of view under pressure.

Nice To Haves

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).

Responsibilities

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.

Benefits

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.

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