Director, Large Enterprise Sales

About Us:

Braintree builds products that make payments easier—so easy that they fade into the background, making entirely new kinds of interactions possible. Interactions like seamlessly paying for your ride share—or the condo you rented this weekend—without presenting a card or pressing a button, or buying a lamp on Pinterest...right from Pinterest. The Braintree full-stack payment platform lets companies build their own experiences and then scale their businesses around the globe. We're known for our technology but we're also known for our support, with internal risk and underwriting, account management and technical support teams who ensure a frictionless payments experience.

Acquired by PayPal in 2013, Braintree is now in an even greater position to change the way people pay. Headquartered in Chicago, Braintree has offices in San Francisco, New York, Sydney, London with employees stationed around the world.

The best talent deserves the best perks. Join the Braintree Team and you’ll get catered lunches, tuition reimbursement, public transit commute reimbursement, and much more! 

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The Director, Large Enterprise North America Sales is responsible to develop the strategy and drive execution to meet or exceed sales and customer objectives through creation and leadership of both an outbound (hunting) Field Sales Team.

This role requires a significant track record of sales leadership within large and small  organizations and ability to champion the sales strategy, implement and contribute to change initiatives to accelerate growth and customer experience, and build a Field Sales team with exceptional sales talent while creating a positive, results-driven, professional culture.

The ideal candidate will be a hands-on, high energy individual who thrives in ambiguity and enjoys a challenge. This an excellent opportunity for someone who is passionate about driving sales strategy in a dynamic environment and has proven ability to take ideas to execution.

This leader will need to have fluency with technology trends shaping the market and be able to interact productively with product leaders to drive customer led innovation. The leader must be focused on exceeding pipeline, sales, revenue, operational and strategic goals as well as the professional growth, development and success of their team members.  

Primary Responsibilities:

  • Develops and defines the vision and associated strategy and execution of plans to achieve annual sales targets and key business results. Develops and implements new sales models to drive incremental growth via new customer acquisition.  
  • Continuously builds sufficient pipeline and effectively manages the stages of such pipeline; conducts sales forecasts, demand generation, deal strategy development and trend analysis. Monitors all sales and other key performance metrics.
  • Leads from strategy to execution on sales initiatives. Works with marketing, risk, legal and product development teams to implement initiatives. Ensures initiatives are reflective of the goals, priorities of other company divisions as appropriate.  
  • Builds, develops and manages a high performing sales team that competes and wins together.
  • Develops sales process to lead an accountable sales force. Defines and ensure execution of sales policies and practices for managing sales performance.
  • Serves as a catalyst for change and continuous improvement. Recommends improvements to sales strategies based on market research and competitor analysis.
  • Manages budgeted headcount and related expenses to deliver against goals.
  • Demonstrated ability to deliver results under pressure and adapt to changing business requirements; ability to plan, organize and manage multiple priorities.


  • 15 years of relevant field management sales experience, including exposure to significant growth oriented business that is globally dispersed.
  • An understanding of Field Sales processes and Sales Development metrics and the ability to build develop new markets from scratch.
  • Must have a proven track record of success in meeting sales targets, familiarity with consultative selling methodologies and experience driving customer led innovation.
  • Drive for results; bias towards action. Able to work in fast-paced, self-directed ambiguous environment. Think like an owner. Open to personal change and continuous improvement.
  • Proven leadership in building, developing, and retaining high performing teams.
  • Bachelor’s Degree in a related field; MBA preferred
  • Travel up to 50% of time 

We know the confidence gap and imposter syndrome can get in the way of meeting spectacular candidates. Please don't hesitate to apply. You can also check out our FAQ!


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