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Head of Business Operations

| Chicago

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! 

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


Head of Business Operations

Braintree – a PayPal Company - is looking for a collaborative and strategically oriented Business Operations professional to lead the BizOps function supporting the Braintree leadership team and broader organization. This individual will support a range of multi-disciplinary operating rhythms and transformation initiatives to help shape, implement, and manage the organization’s operating plan and strategy. A successful candidate will have a high degree of both operational excellence, strategic prowess, and the ability to forge and leverage collaborative relationships with executive leaders and others across enterprise, product management, engineering, Finance, Comms and HR teams among others.

Principal Duties Include:

Financial Management

  • Execute on financial strategies and tactics
  • Influence operating budget by balancing risks, opportunities, and investments in collaboration with our Finance partners
  • Lead the development of multi-year financial plans that are aligned with overall enterprise financial metrics

Business Planning

  • Partner across leaders and teams to drive end-to-end cross functional business planning processes, including but not limited to driving strategic alignment between
    • Braintree leadership and their respective organizations
    • Braintree leadership and support functions
    • Braintree BizDev and PayPal Go-To-Market and Sales teams
  • Work with various levels of leaderships team to identify strategic initiatives to run, transform, and grow the business
  • Manage strategic planning processes that culminate in a cohesive set of priorities and execution plans for the organization

Leadership & Influence

  • Drive accountability of leadership team – including Braintree GM – for all actions and initiatives in their respective scopes
  • Through synthesizing external/market facts, internal business signals, and various data sets - develop perspectives and advise leadership on various topics above (Financial, Operational, Organizational, Personnel, etc.)
  • Run cross-functional working team meetings efficiently and effectively, with ability to connect dots and influence key decisions

Organizational and Operating Discipline

  • Work closely with leaders across the organization to develop OKRs and drive KPI setting with partner teams with shared remits (e.g., Sales, Go To Market); develop tools and processes for tracking and managing performance against those goals
  • Establish and drive operating cadences and governance models to optimize organizational execution and communication
  • Structure and execute operational and strategic initiatives by developing work plans, gathering and synthesizing relevant data, leading analysis, and developing recommendations

Organizational Management

  • Inform, influence, and execute organizational strategies on behalf of leadership team; location strategy, hiring pipeline, employee engagement, etc.
  • Identify and prioritize most critical organizational issues to solve and design analytical and operational approaches to solve
  • Develop frameworks and provide strong problem-solving leadership related to shaping strategic focus and operations approach for the organization
  • Ensure effective organizational change execution in partnership with Finance, HR, Comms, and other key organizations

Key Competencies:

  • Superb leadership and influencing skills
  • Experience leading high-performing and influencing without authority
  • High EQ
  • Strong capacity for navigating and building strong partnerships across matrixed organizations
  • Passion for and demonstrated success understanding and fulfilling internal or external customer needs; problem-solver mindset
  • Sharp business judgment, ability to seamlessly oscillate between "big picture" and “deep detail” perspectives and derive insights to drive organizational priorities
  • Strong organizational and analytical skills with ability to move quickly from insight to action
  • Executive presence, strong verbal and written communication
  • Chameleon-like ability to adapt interaction and presentation styles to fit any audience, from young frontline staff to senior executives
  • Exceptional time management skills
  • Ability to manage change and ambiguity with an action-orientation/drive – must thrive in a dynamic environment
  • High energy, strong work ethic, disciplined execution skills, willingness to do whatever it takes to deliver results


  • 8+ years’ experience in operations, strategy and/or finance, preferably in software industry
  • 3 years of program management or relatable project leadership experience
  • MBA not required, but preferred
  • Experience in FinTech a plus

We're a purpose-driven company whose beliefs are the foundation for how we conduct business every day. The Braintree team lives the values of “Ask Why // Care a Lot // Solve Together,” and we hold ourselves to the highest ethical standards, determined to empower an open and diverse workplace, and strive to treat everyone who is touched by our business with dignity and respect. Our employees challenge the status quo, ask questions, and find solutions. We want to break down barriers to financial empowerment. Join us as we change the way the world defines financial freedom.

**PayPal provides equal employment opportunity (EEO) to all persons regardless of age, color, national origin, citizenship status, physical or mental disability, race, religion, creed, gender, sex, pregnancy, sexual orientation, gender identity and/or expression, genetic information, marital status, status with regard to public assistance, veteran status, or any other characteristic protected by federal, state or local law. In addition, PayPal will provide reasonable accommodations for qualified individuals with disabilities.

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
    • GolangLanguages
    • JavaLanguages
    • JavascriptLanguages
    • PythonLanguages
    • RubyLanguages
    • ClojureLanguages
    • RustLanguages
    • ReactLibraries
    • ReduxLibraries
    • Node.jsFrameworks
    • Ruby on RailsFrameworks
    • DropwizardFrameworks
    • CassandraDatabases
    • PostgreSQLDatabases
    • S3Databases


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
Free Daily Meals
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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