Senior Director, Specialized Sales, NAM

PayPal; San Jose (CA); On-site; USD 218,000 - 324,000; Full time

Job summary

PayPal in San Jose, CA, seeks a Senior Director, Specialized Sales to lead a high‑performing team focused on growing merchant partnerships and driving revenue across the Americas. The role owns strategy, competitive positioning, and cross‑functional collaboration with Product, Marketing, Legal, and Finance to scale PayPal's branded checkout and BNPL solutions.

The successful candidate will build a team of ~25 sales specialists, guide complex deals, forecast health of pipelines, and travel up to

Qualifications

• 12+ years relevant experience and a Bachelor’s degree OR Any equivalent combination of education and experience.

Responsibilities

• Own and drive revenue growth targets for the PayPal specialized products across the full team's portfolio, ensuring alignment between merchant needs and PayPal's solutions.
• Build, lead, and develop a team of ~25 sales specialists, including hiring, onboarding, coaching, performance management, and career development.
• Set team structure, territory/account alignment, and coverage model in partnership with front-book and back-book AM leadership.
• Own the health, accuracy, and forecasting of the US branded and unbranded checkout pipeline across the team, including regular reporting to senior leadership.
• Partner with senior internal stakeholders to identify, prioritize, and scale cross‑sell opportunities across the portfolio.
• Provide senior‑level oversight of complex sales cycles, stepping in on strategic or escalated deals to support discovery, product fit, pricing, negotiation, and contracting.
• Ensure the team executes with excellence across the full sales lifecycle: discovery, product fit consulting, sales pitch, pre‑sales demo, pricing, negotiation, Compliance/UW, KYC/AML, Risk, contract generation, account training, launch‑to‑scale (LTS), and post‑live support.
• Drive team‑wide adoption of structured deal outcomes: co‑marketing, case studies/testimonials, exclusivity or phased co‑existence arrangements, A/B testing, and data sharing.
• Serve as the senior voice of the field to Product, Finance, Legal, Marketing, GTM, and Sales Enablement, shaping roadmap and go‑to‑market priorities based on aggregated customer and team feedback.
• Champion a strong team culture, modeling leadership behaviors, building trust, and driving high engagement and retention across the organization.
• Ensure team proficiency in core tools (Salesforce, Microsoft Word, Excel, PowerPoint) and sales methodology.
• Travel up to 40% of time.

Job description

The Company

PayPal has been revolutionizing commerce globally for more than 25 years. Creating innovative experiences that make moving money, selling, and shopping simple, personalized, and secure, PayPal empowers consumers and businesses in approximately 200 markets to join and thrive in the global economy.

We operate a global, two-sided network at scale that connects hundreds of millions of merchants and consumers. We help merchants and consumers connect, transact, and complete payments, whether they are online or in person. PayPal is more than a connection to third‑party payment networks. We provide proprietary payment solutions accepted by merchants that enable the completion of payments on our platform on behalf of our customers.

We offer our customers the flexibility to use their accounts to purchase and receive payments for goods and services, as well as the ability to transfer and withdraw funds. We enable consumers to exchange funds more safely with merchants using a variety of funding sources, which may include a bank account, a PayPal or Venmo account balance, PayPal and Venmo branded credit products, a credit card, a debit card, certain cryptocurrencies, or other stored value products such as gift cards, and eligible credit card rewards. Our PayPal, Venmo, and Xoom products also make it safer and simpler for friends and family to transfer funds to each other. We offer merchants an end‑to‑end payments solution that provides authorization and settlement capabilities, as well as instant access to funds and payouts. We also help merchants connect with their customers, process exchanges and returns, and manage risk. We enable consumers to engage in cross‑border shopping and merchants to extend their global reach while reducing the complexity and friction involved in enabling cross‑border trade.

Our beliefs are the foundation for how we conduct business every day. We live each day guided by our core values of Inclusion, Innovation, Collaboration, and Wellness. Together, our values ensure that we work together as one global team with our customers at the center of everything we do – and they push us to ensure we take care of ourselves, each other, and our communities.

Job Summary:

The Senior Director, Specialized Sales is a senior leadership role within the PayPal sales organization, responsible for building and leading a high‑performing team of sales specialists focused on growing and strengthening PayPal merchant partnerships, driving incremental revenue, and accelerating adoption of PayPal's branded checkout, payments, and BNPL solutions across the Americas. This leader owns the strategy and execution for the value‑driven sale of PayPal's suite of specialized solutions. The Senior Director will set the vision for how the team engages named existing accounts and prospects, ensure the team anticipates and counters competitive moves, and instill a hunter/defender mentality across the org. This role partners closely with Account Management leadership, Product, Marketing, Legal, and Finance to structure creative, strategic commercial partnerships at scale.

Job Description:

Essential Responsibilities:

• Provide key inputs as an industry leader and expert.
• Develop and articulate a clear, compelling vision and strategy.
• Inspire others with strategic alignment to company‑wide goals.
• Focus on the long‑term success strategy of the sales development function.
• Lead and mentor senior leaders within the sales development team.

Minimum Qualifications:

• 12+ years relevant experience and a Bachelor’s degree OR Any equivalent combination of education and experience.

Additional Responsibilities & Preferred Qualifications:

Duties and Responsibilities:

• Own and drive revenue growth targets for the PayPal specialized products across the full team's portfolio, ensuring alignment between merchant needs and PayPal's solutions.
• Build, lead, and develop a team of ~25 sales specialists, including hiring, onboarding, coaching, performance management, and career development.
• Set team structure, territory/account alignment, and coverage model in partnership with front-book and back-book AM leadership.
• Own the health, accuracy, and forecasting of the US branded and unbranded checkout pipeline across the team, including regular reporting to senior leadership.
• Partner with senior internal stakeholders to identify, prioritize, and scale cross‑sell opportunities across the portfolio.
• Provide senior‑level oversight of complex sales cycles, stepping in on strategic or escalated deals to support discovery, product fit, pricing, negotiation, and contracting.
• Ensure the team executes with excellence across the full sales lifecycle: discovery, product fit consulting, sales pitch, pre‑sales demo, pricing, negotiation, Compliance/UW, KYC/AML, Risk, contract generation, account training, launch‑to‑scale (LTS), and post‑live support.
• Drive team‑wide adoption of structured deal outcomes: co‑marketing, case studies/testimonials, exclusivity or phased co‑existence arrangements, A/B testing, and data sharing.
• Serve as the senior voice of the field to Product, Finance, Legal, Marketing, GTM, and Sales Enablement, shaping roadmap and go‑to‑market priorities based on aggregated customer and team feedback.
• Champion a strong team culture, modeling leadership behaviors, building trust, and driving high engagement and retention across the organization.
• Ensure team proficiency in core tools (Salesforce, Microsoft Word, Excel, PowerPoint) and sales methodology.
• Travel up to 40% of time.

Key Attributes:

• Leads as a player‑coach with an offensive, hunter mindset — building strategic account and territory plans and instilling that same mentality across the team.
• Fiercely competitive with a strong sense of urgency, able to translate that energy into team‑wide accountability for results.
• Comfortable operating and leading through ambiguity, providing clarity and direction to the team.
• Team‑centric, client‑first leader able to direct and influence senior internal stakeholders and build durable cross‑functional relationships.
• Unwavering focus on the merchant experience, setting the standard for white‑glove pre‑and post‑sale support across the team.
• Intellectually curious and a continuous student of sales leadership.
• Strong program and organizational management skills.
• Flexible, decisive, and an energizing leader to work for and with

Subsidiary: PayPal

Travel Percent: 0

The base pay for this role will depend on where you work and the relevant experience and expertise you bring. The expected range of pay for this role by location is:

Primary Location | Pay Range:

• San Jose, California: ($218,000.00 - $323,950.00 Annually)

Additional Location(s) | Pay Range:

• Chicago, Illinois: ($198,000.00 - $294,250.00 Annually)
• Austin, Texas: ($198,000.00 - $294,250.00 Annually)
• New York City, New York: ($218,000.00 - $323,950.00 Annually)
• Scottsdale, Arizona: ($188,000.00 - $279,400.00 Annually)
• Omaha, Nebraska: ($188,000.00 - $279,400.00 Annually)

Additional compensation for this role may include an annual performance bonus, equity, or other incentive compensation, as applicable.

Our Benefits:

For the majority of employees, PayPal’s balanced hybrid work model offers 3 days in the office for effective in‑person collaboration and 2 days at your choice of either the PayPal office or your home workspace, ensuring that you equally have the benefits and conveniences of both locations.

At PayPal, we’re committed to building an equitable and inclusive global economy. And we can’t do this without our most important asset‑you. That’s why we offer comprehensive, choice‑based programs, to support all aspects of personal wellbeing—physical, emotional, and financial—delivering meaningful value where it matters most. We strive to create a flexible, balanced work culture with a holistic approach to benefits, including generous paid time off, healthcare coverage for you and your family, and resources to create financial security and support your mental health.

Commitment to Diversity and Inclusion

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. If you are unable to submit an application because of incompatible assistive technology or a disability, please contact us at [e-mail].

Belonging at PayPal:

Our employees are central to advancing our mission, and we strive to create an environment where everyone can do their best work with a sense of purpose and belonging. Belonging at PayPal means creating a workplace with a sense of acceptance and security where all employees feel included and valued. We are proud to have a diverse workforce reflective of the merchants, consumers, and communities that we serve, and we continue to take tangible actions to cultivate inclusivity and belonging at PayPal.