About Winona:

Winona is one of the leading telemedicine companies providing HRT for women in menopause. We’ve built all of our technology in house including an EHR, patient care admin system, patient portal, website, marketing technology etc. Winona has two compounding pharmacies and a team of in house physicians providing world-class care via a fully vertically integrated business model.

About the role:

We’re looking for a seasoned Head of Customer Services to lead and scale a high-performing global support organization of ~60 Patient Services Representatives and Team Leads. This leader will own strategy, operations, KPIs, and continuous improvement—while ensuring our patients and customers receive fast, empathetic, and reliable support.

A deep understanding of Intercom is essential. You will be the company’s expert on Intercom workflows, automation, ticketing, reporting, and optimization, driving efficiency and excellence across the support lifecycle.

This is a highly cross-functional role that partners closely with Product, Engineering, Clinical Operations, and Leadership to improve the end-to-end patient experience.

Responsibilities:

Lead, mentor, and develop a global team of ~60 customer service / patient support representatives, team leads, and managers.
Build a strong culture of accountability, empathy, and performance.
Own workforce management, scheduling, and staffing strategies to ensure efficient coverage across time zones.
Implement training, upskilling, and QA programs that elevate team performance and consistency.

Serve as the Intercom platform owner, responsible for admin configuration, rules, workflows, bots, routing, tagging, macros, and reporting.
Identify opportunities to automate, streamline, and improve efficiency using Intercom and adjacent tools.
Partner with Product/Engineering to integrate Intercom with internal systems and ensure data accuracy, reliability, and visibility.
Build dashboards and reporting structures that provide real-time insights into team performance and customer health.

Develop and own the overall customer service strategy, ensuring service excellence at scale.
Define and refine KPIs, SLAs, staffing models, escalation frameworks, and service standards.

Establish and maintain SOPs, playbooks, and QA standards across all support channels (chat, email, phone—customizable).
Ensure compliance with healthcare, privacy, and regulatory requirements (HIPAA, PHIPA, etc., if relevant).

Requirements:

7–10+ years of experience in customer service or patient support leadership roles, ideally in tech-enabled services, healthcare, telemedicine, or high-volume support environments.
3+ years managing large, globally distributed teams (50+).
Expert-level proficiency in Intercom—including admin-level configuration, automation, routing, reporting, and optimization.
Proven experience developing and scaling KPI-driven support operations.
Strong analytical skills with the ability to interpret data and guide strategic decision-making.
Exceptional communication, coaching, and cross-functional leadership abilities.
Comfort working in a fast-paced, high-growth environment with ambiguity.
Experience collaborating closely with Product and Engineering teams is a strong plus.

What’s in it for you?

As full-time member of our team, you’ll enjoy:

Flexible hours
Work wherever you choose
Fun and casual work environment
Employee engagement activities and virtual gatherings
We are a diverse, global team! 🌍

This company is affiliated for recruitment efforts. Each entity maintains operational independence, and no personal data is shared between them except as necessary for coordinated recruitment activities. Both teams are committed to protecting applicant privacy and ensuring a respectful, transparent hiring process.

Equal Employment Opportunity

Winona provides equal employment opportunities to all qualified individuals without regard to race, color, religion, sex, gender identity, sexual orientation, pregnancy, age, national origin, physical or mental disability, military or veteran status, genetic information, or any other protected classification. Equal employment opportunity extends to all aspects of employment including, but not limited to, recruitment, hiring, training, promotion, demotion, transfer, leaves of absence, and termination. Winona takes allegations of discrimination, harassment, and retaliation seriously and will promptly investigate such behaviors.