Executive Engagement Lead, Office of the CRO

StripeStripe·Remote(NYC, SF, SEA, CHI, Remote)
Other
GTM

WFA Digital Insight

As remote work continues to redefine the global job market, demand for skilled professionals in digital marketing and paid media has surged. With a staggering 25% growth in the fintech industry in 2025, companies like Stripe are seeking experts who can drive business growth through strategic engagement. The Executive Engagement Lead role stands out for its focus on building and maintaining high-stakes relationships with key customers and partners. To succeed, candidates will need a deep understanding of GTM strategies and exceptional communication skills. With Stripe's commitment to increasing the GDP of the internet, this role offers a unique chance to be part of a team shaping the future of global commerce.

Job Description

## About the Role The Executive Engagement Lead is a pivotal role within the Office of the CRO at Stripe, focusing on developing and executing the strategy for external engagement with key customers, partners, and the executive community. This position requires a deep understanding of GTM strategies, exceptional communication skills, and the ability to build and maintain high-stakes relationships. As part of the Office of the CRO, this role is central to ensuring the CRO's time is utilized effectively and strategically, driving business growth through intentional engagement.

The role involves working closely with the Chief of Staff and other key stakeholders to identify opportunities for executive engagement, develop strategic briefings, and design executive engagement programs that make a lasting impact. Given the expanding enterprise footprint of Stripe, this role is crucial in positioning the company for continued success in the fintech industry.

The Executive Engagement Lead will be part of a dynamic team that is passionate about driving business growth through innovative strategies and external partnerships. With a focus on collaboration, creativity, and strategic thinking, this role offers a unique opportunity to be part of a team that is shaping the future of global commerce.

## What You Will Do - Develop and execute a comprehensive strategy for executive engagement, focusing on key customers, partners, and the executive community.

  • Build and maintain a live view of the CRO's strategic customer relationships, ensuring the CRO's external time is intentional and sequenced.
  • Own the end-to-end executive briefing process for the CRO's strategic user and partner meetings.
  • Design and implement executive engagement programs that make executive engagement a repeatable GTM motion.
  • Map and maintain a multi-threaded view of how the full Stripe executive team connects with each strategic account, tracking the cadence and recency of interactions.
  • Translate executive engagement programs into scalable frameworks and playbooks for the broader GTM leadership team.
  • Collaborate with GTM account teams and field leadership to synthesize account context, competitive dynamics, relationship history, and meeting objectives into high-quality briefings.
  • Ensure the right moments for executive engagement are planned and executed, including dinners, roundtables, conferences, and executive visits.
  • Track open commitments and follow-through, ensuring the CRO is fully prepared for all engagements.
## What We Are Looking For - Experience in a similar role, preferably within the fintech or digital marketing industry, with a focus on executive engagement and GTM strategies.
  • Deep understanding of GTM strategies and their application in driving business growth.
  • Exceptional communication and interpersonal skills, with the ability to build and maintain high-stakes relationships.
  • Strong strategic thinking and problem-solving skills, with the ability to design and implement effective executive engagement programs.
  • Ability to work closely with senior leadership and cross-functional teams, including GTM, sales, and marketing.
  • Experience in synthesizing complex information into actionable insights and strategic briefings.
  • Strong project management skills, with the ability to prioritize tasks, manage multiple projects, and meet deadlines.
  • Familiarity with tools and platforms used for GTM strategies, executive engagement, and relationship management.
## Nice to Have - Previous experience working in a fast-paced, dynamic environment, preferably within a startup or growth-stage company.
  • Knowledge of the fintech industry and its key players, with an understanding of the challenges and opportunities facing the sector.
  • Experience in designing and implementing executive sponsorship frameworks and criteria for senior leader deployment.
  • Familiarity with event and cadence programming that creates structured C-suite moments at scale.
## Benefits and Perks - Competitive compensation package, reflecting the importance of this role to Stripe's continued growth and success.
  • Opportunities for professional growth and development, including training and education programs focused on GTM strategies and executive engagement.
  • Comprehensive health insurance package, including medical, dental, and vision coverage.
  • Generous PTO policy, allowing for a healthy work-life balance and the opportunity to recharge.
  • Remote work stipend, supporting the establishment of a productive home office environment.
  • Access to the latest tools and technologies, ensuring the ability to perform at the highest level.
  • Collaboration with a talented and passionate team, driven by a shared vision of increasing the GDP of the internet.

How to Stand Out

- Develop a deep understanding of GTM strategies and their application in driving business growth, as this will be crucial in designing effective executive engagement programs.

  • Showcase exceptional communication and interpersonal skills through your resume and cover letter, highlighting experiences where you built and maintained high-stakes relationships.
  • Prepare to discuss your approach to strategic thinking and problem-solving, providing examples of how you've designed and implemented successful executive engagement programs in the past.
  • Be ready to talk about your experience working with senior leadership and cross-functional teams, and how you handled challenging situations or conflicts.
  • Ensure your portfolio includes examples of strategic briefings or executive engagement plans you've developed, demonstrating your ability to synthesize complex information into actionable insights.
  • When negotiating salary, consider the competitive compensation package and the value you bring to the role, ensuring your expectations are aligned with industry standards.
  • Be cautious of roles that lack clarity on expectations or responsibilities, as this can indicate a lack of structure or support within the organization.

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