Director of Competitive Intelligence

Guidewire Software•San Mateo, CA

3d•$178,000 - $313,000

About The Position

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.
Strong executive communication skills for briefing C-level leaders and defending a clear point of view under pressure.
Strong analytical skills, comfortable with both qualitative (interviews) and quantitative data (win/loss stats, pipeline metrics).

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.

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.