Executive Engagement Lead, Office of the CRO

Stripe • Chicago, IL

2d

About The Position

Stripe is a financial infrastructure platform for businesses. Millions of companies—from the world’s largest enterprises to the most ambitious startups—use Stripe to accept payments, grow their revenue, and accelerate new business opportunities. The Office of the CRO sits at the center of Stripe's global revenue organization and operates on two tracks: running the operating rhythm that keeps a global GTM motion on-cadence, and serving as the CRO's thinking partner on Stripe's most important commercial bets. This role is the first dedicated executive engagement hire in the structure, and the work you produce directly shapes how Stripe's most senior revenue leader shows up in their highest-stakes moments. As the Executive Engagement Lead, you will own the strategy and substance of how Stripe's CRO engages users, partners, and the executive community. As external demands grow and Stripe's enterprise footprint expands, this role gives the CRO a dedicated force multiplier on the moments that matter most. Working in close partnership with the Chief of Staff, you will take on and build out the executive engagement function as the Office of the CRO scales. You are not the logistics coordinator — you are the architect of what happens in the room and why it matters.

Requirements

• 6+ years of experience in sales, executive engagement, strategic customer programs, chief of staff, management consulting, or a closely related discipline — with demonstrated proximity to C-suite executives in a support, advisory, or program role.
• Exceptional written communication skills, with executive voice, precision, and economy.
• Strong program design and execution track record, including building engagement programs, frameworks, or operating cadences from scratch, driving adoption, and measuring results.
• Deep cross-functional credibility, ability to earn trust quickly with senior stakeholders, navigate ambiguity without losing momentum, and align people around a shared direction without needing positional authority.
• Experience preparing a senior executive for a high-stakes customer meeting as an active contributor to the outcome.
• High executive presence, representing the Office of the CRO internally and externally.

Nice To Haves

• Prior experience in a chief of staff, executive advisory, or strategic programs role supporting a CRO, CEO, or equivalent C-suite executive at a high-growth technology company.
• Experience designing and running executive customer programs: Executive Engagement programs, executive advisory councils, C-suite roundtables, or strategic account engagement frameworks.
• Track record working with enterprise accounts at the executive level, understanding what motivates C-suite buyers, how relationships develop, and where Stripe fits in a customer's strategic agenda.
• Familiarity with Stripe's GTM motion, products, and the enterprise sales cycle.
• Experience at a top-tier management consulting firm or investment bank with significant client-facing and executive communication responsibilities.
• Comfort with data and CRM tools to inform engagement strategy and track relationship health across strategic accounts.

Responsibilities

• Build and maintain a live view of the CRO's strategic customer relationships, ensuring the CRO's external time is intentional and sequenced across Stripe's most important users and partners.
• Track open commitments and follow-through, and ensure the right moments — dinners, roundtables, conferences, flagpole events, executive visits — are far enough in the planning horizon to be purposeful.
• Own the end-to-end executive briefing process for the CRO's strategic user and partner meetings, synthesizing account context, competitive dynamics, relationship history, and meeting objectives into high-quality briefings.
• Build the program that makes executive engagement a repeatable GTM motion, designing the operating model for how Stripe's executives get deployed in service of the organization's most important user relationships.
• Design executive sponsorship frameworks, criteria for when and how GTM teams bring senior leaders into deals, and event and cadence programming that creates structured C-suite moments at scale.
• Build and maintain a multi-threaded view of how the full Stripe executive team connects with each account for Stripe's most critical user relationships.
• Map which Stripe leaders have active relationships at each strategic account, track the cadence and recency of those interactions, and surface gaps in coverage before they become relationship risks.
• Translate the programs and standards built for the CRO into scalable frameworks and playbooks the broader GTM leadership team can use.
• Set the bar for executive engagement across the organization, enabling a GTM org that runs these moments well, consistently, without everything running through the Office.

What This Job Offers

• Job Type: Full-time
• Career Level: Executive
• Education Level: No Education Listed