Sr. Director, Regional Enablement (Americas)

Hims & Hers

120d

About The Position

As Senior Director, Regional Enablement (Americas) at Hims & Hers, you will lead the development and execution of our regional operational strategy across North and South America. Your mission: to enable compliant, scalable growth by supporting our business goals via thoughtful operating models that align with local regulatory environments. This role goes far beyond implementation—you will lead a team that researches, strategizes, and operationalizes the infrastructure needed to enter new countries or scale in existing ones. Your team will evaluate the regulatory landscape and craft solutions that allow us to grow while staying within the guardrails of pharmacy and healthcare regulation. You’ll partner closely with Legal, Regulatory, Strategic Partnerships, and Product to develop country-specific playbooks, and you will own the execution of those plans.

Requirements

• 12+ years of experience in operations strategy, regulatory implementation, or international expansion—preferably in pharmacy, healthcare, or digital health.
• Deep understanding of U.S. pharmacy regulations and the ability to interpret and navigate similar frameworks in international markets.
• Proven experience launching and scaling operations in new markets, with direct ownership of regulatory feasibility and partner execution.
• Strong team leadership skills—you’ve built and managed teams that execute under pressure and across time zones.
• High degree of cross-functional fluency—you know how to engage Legal, Regulatory, Product, and Ops as strategic collaborators.
• Strategic mindset, with the ability to zoom into operational detail and zoom out to guide executive decision-making.
• French, Spanish and/or Portuguese fluency is a strong plus given the regional scope.

Responsibilities

• Serve as the strategic owner of operational enablement for new and existing markets across the Americas.
• Translate high-level business expansion goals into tailored, actionable operational strategies grounded in local market realities.
• Act as a thought partner to the business team, offering early-stage insights that influence market prioritization and sequencing.
• Identify and interpret regulatory constraints for pharmacy, telehealth, fulfillment, and care delivery in new and existing markets.
• Assess the impact of regulations on the Hims & Hers preferred operating model and recommend compliant solutions that preserve scalability and service quality.
• Proactively partner with Legal and Regulatory to ask the right questions, map critical dependencies, and de-risk launches from a compliance standpoint.
• Develop repeatable, adaptable market launch and scale-up playbooks to reduce execution time and complexity.
• Lead post-launch optimization efforts to improve service levels, reduce cost, or enhance regulatory compliance in live markets.
• Track market performance against key operational KPIs and identify opportunities for improvement.
• Partner with Strategic Partnerships to evaluate and activate regional fulfillment, pharmacy, manufacturer, or infrastructure partners.
• Work closely with Real Estate, Product, Pharmacy Ops, Transportation, and Supply Chain to ensure market needs are supported with the right physical infrastructure.
• Lead a high-performing regional enablement team responsible for both strategy and execution.
• Ensure your team delivers on market launches and optimization projects in a timely, cost-effective, and compliant manner.

Benefits

• Competitive salary & equity compensation for full-time roles
• Unlimited PTO, company holidays, and quarterly mental health days
• Comprehensive health benefits including medical, dental & vision, and parental leave
• Employee Stock Purchase Program (ESPP)
• 401k benefits with employer matching contribution
• Offsite team retreats

What This Job Offers

• Job Type: Full-time
• Career Level: Senior
• Number of Employees: 11-50 employees