Senior Director, Specialized Sales, NAM

PayPal; Chicago (IL); Hybrid; USD 177,000 - 294,000; Full time

Benefits offered by this job

Hybrid work model

Health insurance

Paid time off

Job summary

PayPal is seeking a Senior Director of Specialized Sales in the United States to lead a high-performing team focused on merchant partnerships and revenue growth across the Americas. This leader will own the strategy for selling specialized PayPal solutions and drive adoption of branded checkout, payments, and BNPL offerings.

The role requires 12+ years of experience with a Bachelor’s degree and involves risk, pricing, and complex deal negotiations.

Qualifications

• 12+ years of relevant sales leadership experience.
• Bachelor’s degree or equivalent combination of education and experience.

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.
• Own and drive revenue growth targets for the PayPal specialized products across the full team's portfolio.
• 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.

Skills

12+ years experience

Education

Bachelor’s degree

Tools

Salesforce

Microsoft Office

Job description

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.

Key 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.

Additional 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.

Minimum Qualifications:

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

Pay Range:

• 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)
• Additional Location(s) | Pay Range: Austin, Texas: ($198,000.00 - $294,250.00 Annually)
• Additional Location(s) | Pay Range: New York City, New York: ($218,000.00 - $323,950.00 Annually)
• Additional Location(s) | Pay Range: Scottsdale, Arizona: ($188,000.00 - $279,400.00 Annually)
• Additional Location(s) | Pay Range: Omaha, Nebraska: ($188,000.00 - $279,400.00 Annually)

Additional Compensation:

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

Our Benefits:

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.

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.

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.