Director, Account Management - Insurance & Healthcare

PayPal•Chicago, IL

62d•Hybrid

About The Position

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.

Requirements

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

Nice To Haves

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.
Deep understanding of regulatory environments, procurement processes, and enterprise client needs in Healthcare and Insurance space.

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.
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.