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Head of Product Sales, Optimized Checkout

Stripe

Stripe

Product, Sales & Business Development
South San Francisco, CA, USA
USD 457k-685,400 / year + Equity
Posted on Dec 10, 2025
Apply now

Who we are

About Stripe

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. Our mission is to increase the GDP of the internet, and we have a staggering amount of work ahead. That means you have an unprecedented opportunity to put the global economy within everyone's reach while doing the most important work of your career.

About the team

Stripe is investing in building out its Optimized Checkout product sales team to actively engage prospects and customers to help them transform their business through building on Stripe’s platform. You will represent Stripe across all our global markets externally, and you will also maintain and develop our culture internally. You know what it is like to build and scale a business structurally and methodically. You will have a strong understanding of technical concepts, and enjoy being close to product and engineering teams as well as broader sales teams.

As the Head of Product Sales, Optimized Checkout you will be a critical part of the go-to-market leadership team, driving strategy and operations for Stripe’s Optimized Checkout GTM resulting in accelerated revenue growth across the Optimized Checkout Suite, Adaptive Pricing, Managed Payments, Alternative Payment Methods, and Orchestration product areas.

What you’ll do

  • Own and drive the global GTM strategy for Optimized Checkout.
  • Lead a high-performing global team helping them deliver on ambitious targets across four key product areas: Optimized Checkout Suite, Adaptive Pricing, Managed Payments, Alternative Payment Methods, and Orchestration.
  • Work in partnership with Product, GTM, Product Marketing and Finance to align on the Optimized Checkout GTM strategy and product roadmap to meet our customer needs and accelerate our growth globally.
  • Partner cross functionally and operate at the highest level in a matrix organization, working with multiple functions across the business to deliver to our revenue goals.

Responsibilities

  • We are looking for an executive who has a proven track record of building teams, delivering outstanding results with a user first obsession for the long term. A leader who thrives on dealing with ambiguity, operating in a high-growth environment and solving complicated problems.
  • Ideal candidates will have core sales management and leadership experience bringing new products to market, developing GTM strategy, scaling a technology sales team, excellent communication skills, and a users first obsession.
  • Recruit, develop and lead a global team focused on the Optimized Checkout business across AMER, EMEA, and APAC.
  • Coach and guide the team in developing consultative and solution-based sales skills through all facets of the sales cycle.
  • Create structure and focus for GTM ideas and product sales campaigns that the product team is exploring. Drive execution and measurement. Analyze results and make recommendations for action in a timely manner.
  • Manage day-to-day operations, with a focus on performance against key sales metrics.
  • Drive revenue, increase attach rates, and acquire new users at high rates of growth.
  • Get hands on engaged in the largest, most strategic opportunities, leading executive relationships and helping the team win new customers.
  • Lead with clarity and context with a compelling plan in line with Stripe’s direction.
  • Constantly innovate and improve programs and program management mechanisms, suggesting new ideas, sharing best practices, and improving the business and customer engagement model.

Who you are

We're looking for someone who meets the minimum requirements to be considered for the role. If you meet these requirements, you are encouraged to apply. The preferred qualifications are a bonus, not a requirement.

Minimum requirements

  • 15+ years of technology sales experience
  • 10+ years of people leadership experience
  • 3+ years of experience in payments or financial services industry
  • Experience as a builder who can drive immediate results and rapidly grow the business
  • Passion for building and scaling - you have previously built out the team and operations for a technology company
  • Excellent relationship building skills with deep experience communicating with and engaging customers and at all levels
  • Ability to explain complex issues in clear, non-technical language and successfully attract new business
  • Detailed oriented and excited to help a team navigate all of the operational aspects of a growing organization and office
  • Highly analytical and a deep understanding of how to leverage the data that impacts revenue teams
  • You can think globally, act regionally, and thrive in a multi-cultural startup environment
  • Experience representing an organization publicly and are comfortable communicating with the press, regulators, and our internal employees
  • High energy, strong work ethic, disciplined execution skills, willingness to do whatever it takes to deliver results
  • True team player - always
Office-assigned Stripes in most of our locations are currently expected to spend at least 50% of the time in a given month in their local office or with users. This expectation may vary depending on role, team and location. For example, Stripes in our Bucharest, Romania site have an 80% in-office expectation, and those in Stripe Delivery Center roles in Mexico City, Mexico and Bengaluru, India work 100% from the office. Also, some teams have greater in-office attendance requirements, to appropriately support our users and workflows, which the hiring manager will discuss. This approach helps strike a balance between bringing people together for in-person collaboration and learning from each other, while supporting flexibility when possible.

The annual US base salary range for this role is $457,000 - $685,400. For sales roles, the range provided is the role’s On Target Earnings ("OTE") range, meaning that the range includes both the sales commissions/sales bonuses target and annual base salary for the role. This salary range may be inclusive of several career levels at Stripe and will be narrowed during the interview process based on a number of factors, including the candidate’s experience, qualifications, and location. Applicants interested in this role and who are not located in the US may request the annual salary range for their location during the interview process.

Additional benefits for this role may include: equity, company bonus or sales commissions/bonuses; 401(k) plan; medical, dental, and vision benefits; and wellness stipends.

Office locations

South San Francisco HQ, or New York

Team

Sales

Job type

Full time

Apply for this role
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