Director of Software Engineering at Braintree

| Chicago
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Director of Software Engineering

About Us:

Braintree lets you move money from one place to another safely and securely. Every time you pay for an Uber ride, book a stay through Airbnb, or pay with PayPal when you check out online, you’re probably using our product. It sounds complex (and it is), but we make it so frictionless.

We solve world-scale problems and provide opportunities to match. We build diverse teams that recognize our strengths and allow us to work on our weaknesses. You bring skills and a relentless focus on the customer, and we'll provide the support you need to do the best work of your life.

Check us out: GitHub | Blog | Twitter | LinkedIn | Facebook | The Muse | Glassdoor

Director of Engineering:

We are building a modern, global scale online payment platform to support merchants grow their business. The scope of the software engineering efforts includes seamless on-boarding of merchants onto our platform, delightful experience while using the platform on a daily basis, and supporting the merchant’s growth plans with excellent payment experience for their customers across the globe. As a result, we are seeking a seasoned engineering leader to set strategy, define roadmaps, and lead multiple engineering teams in creating a world class service. This individual must also have a strong technology leadership and management skills as well as a business orientation and ability to communicate with both technical and non-technical teams. They must possess a proven ability to work with existing applications and processes and successfully migrate or interface those with newer technologies and improved processes.

Reporting directly to the Head of Product Engineering, this leader will have the following responsibilities:

  • Translate business objectives and product strategy into execution strategy (tactical and strategic) and product roadmap.
  • Design and deliver software engineering solutions that enable fast, efficient deployment of well tested code to production.
  • Keep product management leaders informed and onboard with strategies and roadmaps through transparent communications and personal relationships.
  • Drive the rollout of major updates, strategic changes, and roadmap changes with products and technology teams and extended PayPal stakeholders.
  • Develop periodic updates and readouts on product delivery progress for all team initiatives based on audience (technical and non-technical, internal and across PayPal).
  • Design and staff a world-class engineering organization leveraging both internal and external candidates required to innovate, build, and operate in-scope services.
  • Provide end to end plans for major initiatives and product offering that ensures measurability, ongoing sustainability, and high-quality production operations.
  • Develop trusted relationships with key technology and functional leaders & stakeholders to drive focus on the strategic and tactical objects for areas including CI/CD, compute orchestration, and monitoring.
  • Understand PayPal initiatives in related areas to both contribute thought leadership and identify synergies.
  • Create a collaborative environment that fosters autonomy, mastery, and purpose; promotes continuous improvement that results in an effective outcome driven organization.
  • Drive for clarity to keep teams moving forward.
  • Provide “go to” leadership, transparency and visibility to the entire Technology & Products organization

This role will have to work in very close partnership with the Head of Platform and Infrastructure and may upon occasion represent the voice of the Platform Leadership team.

Role Requirements

Technical Acumen

  • 15+ years of engineering management experience showing progression from single team to multiple team / multiple domain leadership through organizational and business leadership.
  • Thorough understanding of product development processes and lifecycle; ability to adjust and apply this knowledge in leading teams in a dynamic environment using iterative methodologies.
  • Outstanding organizational, communication, interpersonal, relationship building skills conducive to collaboration and customer focus
  • Excellent analytical and problem solving skills with a history of hands-on, detail orientation.
  • Ability to establish credibility and rapport with senior executives and technical and non-technical team members alike.
  • Ability to successfully roll-in the DevOps culture within software engineering teams so that the teams thrive in building secure, scalable software products assisted by automation and engineering excellence
  • Experience as a Engineering Manager and/or roles in engineering is mandatory.
  • Experience framing, establishing and implementing large-scale (enterprise-level) change initiatives.
  • A service oriented minded person who is a customer champion

Business Acumen

  • Outstanding communication skills, permitting complex technical matters to be understood by business professionals
  • Balances technical and commercial acumen; able to communicate “what is possible” and what will have the biggest impact on the business
  • Able to articulate and manage to key OKRs and use metrics to drive performance and provide data in support of key decisions

Setting Strategy

  • Sees the “bigger picture” and understands how Braintree can benefit from leveraging compute resources on the public cloud, and creates customized developer tooling and automation procedures to continuously deploy cloud-native applications.
  • Stays abreast of key industry actions and their implications or opportunities to Braintree

Executing for Results

  • Prepares realistic estimates of resource requirements (e.g., budget, headcount) needed to accomplish team objectives
  • Balances urgent and effective action, commitment to excellence, and taking initiative to resolve problems; holds internal stakeholders accountable where appropriate
  • Capable of executing short-term (tactical) and long term (strategic) plans
  • Able to demonstrate examples of strategic enterprise-wide solutions that were conceptualized & rolled out across a division/enterprise

Leading Teams

  • Ability to drive the execution of multiple cross-company initiatives and analyses and deliver quality work on time with multiple, competing priorities
  • Defines and translates a vision into actionable plans
  • Build and lead a team of experts in CI/CD, Kubernetes, and Production Observability.

Building Relationships and Using Influence

  • Have a high emotional intelligence that lends itself to working with a wide range of people converting stressful situations to calm objective conversations
  • Ability to influence and achieve alignment across a range of different opinions and interests
  • Strong communication, listening, and negotiation skills; able to convey important messages in a clear and compelling manner
  • Develops loyalty and commitment in others by articulating an appealing vision for the future, communicating high expectations, developing and mentoring direct reports, and setting an example in one’s own behavior

We know the confidence gap and imposter syndrome can get in the way of meeting spectacular candidates. Please don't hesitate to apply.


  • Open dev days: every two weeks we spend a day working on projects that interest us and help us expand our skills and knowledge
  • Participation in the technology community: we help cover travel and attendance costs for conferences, and we offer opportunities and tools for speaking.
  • Check out our Careers page for more company perks.
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Technology we use

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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
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