Director, Account Management – Insurance & Healthcare

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 Director of Account Management for Insurance & Healthcare is a critical leadership role responsible for driving PayPal’s growth in two of the most complex and regulated industries. This leader will define and execute vertical strategy, deepen relationships with top enterprise clients, and ensure PayPal solutions address the unique needs of insurers, providers, payers, and related ecosystem partners.

Reporting directly to the VP of Large Enterprise, the Director serves as a trusted advisor and cross-functional leader, partnering with Product, Risk, Compliance, Legal, Data Science, and Operations to deliver sustainable, compliant, and scalable growth.

Job Description:

Essential Responsibilities:

• Develop and influence business strategies for organizational success.
• Provide strategic counsel to executive leadership.
• Lead initiatives that drive significant business impact.
• Collaborate with cross-functional teams to align strategies.
• Monitor industry trends to inform strategic decisions.

Expected Qualifications:

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

The Director leads a team of Account Managers and Business Development professionals, balancing aggressive growth goals with compliance, data privacy, and security requirements. Success in this role requires expertise in navigating regulatory environments (HIPAA, state/federal insurance regulation), understanding the digital transformation of healthcare and insurance payments, and delivering innovative solutions that enhance customer and patient experiences.

Responsibilities:

• Own and drive growth strategy across healthcare and insurance while ensuring alignment with PayPal’s, and long-term strategic objectives.
• Deep understanding of regulatory environments, procurement processes, and enterprise client needs in Healthcare and Insurance space.
• Lead a high-performing group of first line leader(s) and senior Account Managers and Business Development professionals, setting clear priorities, coaching for excellence, and ensuring consistent execution across complex and regulated environments.
• Establish and maintain executive-level relationships with key merchants, positioning PayPal as a strategic partner that enables innovation while managing risk and compliance expectations.
• Oversee negotiation of complex commercial agreements, ensuring deals drive mutual value while adhering to internal policies and industry pricing standards.
• Monitor portfolio performance and ensure strong execution on revenue retention, cross-sell, and expansion opportunities, balancing aggressive growth with disciplined risk management.
• Champion operational excellence, ensuring smooth onboarding, integration, and support across large strategic accounts with rapid scaling needs or unique technical and legal complexities.
• Build and scale account strategies tailored to vertical-specific dynamics, ensuring teams proactively identify merchant pain points, product opportunities, and partnership white space.
• Establish portfolio pricing sales and account practices, ensuring merchant health is continuously monitored and loss rates remain below plan through proactive interventions.
• Lead renewal and churn mitigation strategies for complex and often volatile accounts, ensuring high merchant satisfaction, regulatory alignment, and retention.
• Foster a culture of collaboration, integrating deeply with cross-functional stakeholders to ensure full transparency and alignment across deal cycles, pricing reviews, and product adoption.
• Encourage leveraging competitive and industry insights to refine account strategies and influence PayPal’s broader business initiatives.
• Advocate for merchant needs within PayPal by driving innovation and ensuring solutions align with evolving market demands.

Qualifications:

• 10+ years of experience in payments, e-commerce, or fintech, with 5+ years directly leading teams or portfolios within high-risk or highly regulated verticals.
• Expertise in dynamic pricing schemes, and real-time data platforms, with a strong command of the operational and technical levers required to scale responsibly.
• Proven track record of closing $100M+ multi-product commercial deals with C-suite stakeholders across complex, enterprise-level engagements.
• Proven people leader with the ability to scale high-performing group while maintaining velocity, executional excellence, and team cohesion.
• Exceptional communication and negotiation skills, with a demonstrated ability to influence internal and external stakeholders and secure mutually beneficial outcomes in complex deal structures.
• Strategic and analytical thinker with a proven ability to identify team growth opportunities, address complex challenges, and drive measurable business results.
• Proficiency in CRM tools (e.g., Salesforce) to enable team pipeline management, accurate revenue forecasting, and insightful reporting of sales activities.

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.

Subsidiary:

PayPal

Travel Percent:

0

-

PayPal is committed to fair and equitable compensation practices.

Actual Compensation is based on various factors including but not limited to work location, and relevant skills and experience.

The total compensation for this practice may include an annual performance bonus (or other incentive compensation, as applicable), equity, and medical, dental, vision, and other benefits. For more information, visit https://www.paypalbenefits.com.

The US national annual pay range for this role is $270,000 to $464,200

PayPal does not charge candidates any fees for courses, applications, resume reviews, interviews, background checks, or onboarding. Any such request is a red flag and likely part of a scam. To learn more about how to identify and avoid recruitment fraud please visit https://careers.pypl.com/contact-us.

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.

Our Benefits:

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 benefits to help you thrive in every stage of life. We champion your financial, physical, and mental health by offering valuable benefits and resources to help you care for the whole you.

We have great benefits including a flexible work environment, employee shares options, health and life insurance and more. To learn more about our benefits please visit https://www.paypalbenefits.com.

Who We Are:

Click Here to learn more about our culture and community.

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 paypalglobaltalentacquisition@paypal.com.

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.

Any general requests for consideration of your skills, please Join our Talent Community.

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

Notice to Applicants and Employees who reside within New York City. Click here to view the notice.