People Matter

Head of Commercial Sales

Stripe

Stripe

Sales & Business Development
Chicago, IL, USA
USD 415,400-623k / year + Equity
Posted on Jun 27, 2025

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

The Commercial Sales team is focused on driving revenue with mid-market companies in North America and is an important lever for Stripe’s growth. Stripe helps these brands build new business models and drive innovation and modernization. As the Head of Commercial Sales, you will be a critical part of the go-to-market leadership team, leading strategy and execution resulting in accelerated revenue growth with Stripe’s users.

What you’ll do

  • Drive sales growth through successful leadership, organizational planning, customer service and outstanding execution of all regional Commercial programs.
  • Oversee the expansion of Stripe’s existing mid-market (Commercial segment) footprint.
  • Develop and refine Stripe’s global Commercial strategy, guiding investment decisions with Product, Engineering, Marketing, and other supporting teams.
  • Make hiring decisions, honing our ideal candidate profile and onboarding strategy.
  • 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.
  • Define key sales support mechanisms, processes, and programs to meet the rapid growth of the business and achieve revenue attainment and market development objectives.
  • Build a world-class organization and write the playbook for the era of consumption-based, API-driven sales.

Responsibilities

  • Develop the long-term vision and strategy for a growing Commercial team, and scale day-to-day operations.
  • Adopt and influence the company's sales methodology/process and drive best practices on selling and forecasting.
  • Lead initiatives to innovate sales processes and strategies, incorporating new technologies and methodologies to maintain a competitive edge.
  • Develop best practices that enable the organization to more rapidly scale to deliver on revenue targets and support KPIs for growth.
  • Engage with the largest strategic opportunities, leading executive relationships and helping the team win new customers.
  • Develop contingency plans and manage challenges proactively, addressing customer concerns and competitive pressures
  • Effectively work cross-functionally across the organization to shape Stripe's product roadmap to meet customer needs.
  • Build and develop a high-performing team, foster a strong culture of energized and engaged Stripes, invest in the growth and development of your team.

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.

Minimum requirements

  • 15+ years of people management experience, including second line management.
  • Experience leading mid-market Sales organizations in a high-growth technology environment.
  • Prior experience in the payments industry, card issuing or financial services.
  • Prior experience with mid market is a plus.
  • Experience building high caliber teams across multiple regions, including launching teams in new offices.
  • Demonstrated ability to build a sales team from the ground up.
  • Ability to hire, train and coach a high-performance sales team.
  • Demonstrated quantitative and analytical skills.
Office-assigned Stripes spend at least 50% of the time in a given month in their local office or with users. This hits a balance between bringing people together for in-person collaboration and learning from each other, while supporting flexibility about how to do this in a way that makes sense for individuals and their teams.

The annual US base salary range for this role is $415,400 - $623,000. 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

Chicago

Team

Sales

Job type

Full time