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Senior Director, Specialized Sales, NAM

October 1, 2026

About the position

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.

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, 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.

Requirements

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

Nice-to-haves

Travel up to 40% of time

Benefits

generous paid time off
healthcare coverage for you and your family
resources to create financial security
support your mental health

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Common Interview Questions And Answers

1. HOW DO YOU PLAN YOUR DAY?

This is what this question poses: When do you focus and start working seriously? What are the hours you work optimally? Are you a night owl? A morning bird? Remote teams can be made up of people working on different shifts and around the world, so you won't necessarily be stuck in the 9-5 schedule if it's not for you...

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This is a great question because it shows your comfort level with technology, which is very important for a remote worker because you will be working with technology over time...