Support Team Leader at Braintree

| Chicago
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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! 

Check us out - Braintree on The Muse | LinkedIn | Glassdoor | Facebook |Twitter

Role Description:

The Support Team Leader position supports the team that provides first-touch technical support to our merchants. We're looking for a highly organized go-getter to lead and motivate a team that consistently delivers on Braintree’s white-glove service experience. Our Support team isn’t your average call center team: they are highly motivated, technically proficient, and stakeholders in company initiatives. Because of this, as a lead, you’ll be expected to provide feedback, coaching, and career guidance to teammates, work with the Support leadership team to address knowledge gaps and training opportunities, assist in building and maintaining a diverse and inclusive workplace, and work with the Head of Support to execute new team strategies.


  • Demonstrate and be a model for Braintree’s Values of Ask Why, Care A Lot, and Solve Together
Ask Why:
  • Utilize data to make decisions and enhance merchant experience and team performance
  • Be a stakeholder for product development and regularly champion Supportreep and merchant feature requests
  • Proactively find opportunities to research and advocate for ways to make our processes better
  • Know which questions to ask to make improvements not only within Support, but within the Braintree organization
Care, A Lot:
  • Motivate, lead, and coach a diverse team of Support Specialists, aka Supportreeps
  • Take a balanced approach to coaching, feedback, and development practices to help teammates improve their performance
  • Monitor agent performance and conduct one on one meetings and performance reviews
  • Create an environment where teammates feel valued and enjoy their jobs
  • Challenge Supportreeps to grow their skill set to help them pursue future career opportunities at Braintree
Solve Together:
  • Be proactive in contributing resources to Supportreeps by providing hands-on support during high volume periods, by serving as an escalation point, and by collaborating to get through the toughest of issues
  • Handle staffing responsibilities by creating and maintaining a daily schedule that balances the needs of the business and our teammates
  • Assist in recruiting and development of support team as a whole
  • Help synthesize and deliver communication between morning, day and night shifts


  • Be someone who believes in Braintree’s Values of Ask Why, Care, A Lot, and Solve Together
  • Experience leading highly collaborative customer service or account management teams working directly with customers or clients to solve together
  • Have an interest and the desire to research, offer up, and implement new approaches on improving team and merchant experiences
  • Be a self-starter, self-learner, and possess incredible resourcefulness
  • Be comfortable dealing with ambiguity and possess the intellectual horsepower to make decisions on the fly
  • Love and understanding of emerging technologies
  • Be comfortable with consistent change - agility is key!
  • Would rather swim in solutions than problems
  • Possess infinite patience and a desire to turn angry customers into happy ones
  • Ability to work autonomously with a high level of responsibility
  • Be a great writer with a keen eye for the nuances of the English language
  • Flexibility with work hours including some weekends and holidays 

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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Technology we use

  • Engineering
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222 Merchandise Mart Plaza, Chicago, IL 60654

An Insider's view of Braintree

What projects are you most excited about?

Braintree is committed to continual improvement in the areas of D&I. We do this by emphasizing our values of Ask Why, Care A Lot, and Solve Together, Ensuring D&I is an ongoing conversation at all levels of the company, offering company-wide D&I trainings, and supporting employee developed events.

Anna Johnson

Diversity & Inclusion Program Manager

How do you empower your team to be more creative?

Working on internal products, I have a direct feedback channel to my teammates, to help fix things when they aren't quite right. Seeing this multiplier effect in action, seeing how it unlocks my teammates to new productive ends, is extremely satisfying.

Andrew Harris

Software Engineer

What are Braintree Perks + Benefits

Friends outside of work
Eat lunch together
Intracompany committees
Daily stand up
Open door policy
Team owned deliverables
Team based strategic planning
Group brainstorming sessions
Pair programming
Open office floor plan
Dedicated Diversity/Inclusion Staff
Unconscious bias training
Diversity manifesto
Someone's primary function is managing the company’s diversity and inclusion initiatives
Health Insurance & Wellness Benefits
Flexible Spending Account (FSA)
Dental Benefits
Vision Benefits
Health Insurance Benefits
Life Insurance
Wellness Programs
Retirement & Stock Options Benefits
401(K) Matching
Company Equity
Employee Stock Purchase Plan
Performance Bonus
Match charitable contributions
Child Care & Parental Leave Benefits
Child Care Benefits
Acme Co. provides Backup child care assistance.
Generous Parental Leave
Family Medical Leave
Adoption Assistance
Company sponsored family events
Acme co. sponsors family oriented events Annually.
Vacation & Time Off Benefits
Unlimited Vacation Policy
Generous PTO
Paid Volunteer Time
Paid Holidays
Perks & Discounts
Beer on Tap
Casual Dress
Commuter Benefits
Game Room
Stocked Kitchen
Professional Development Benefits
Job Training & Conferences
Tuition Reimbursement
Diversity Program
Cross functional training encouraged
Promote from within
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