DearDoc - Head of Customer Success

Who we are…

DearDoc provides top doctors with a suite of technology and marketing tools to make communication between patients and doctors a more accessible, modern, and seamless experience. Serving over 4,500+ practices, DearDoc enables doctors to focus on what they do best: providing great patient care. Our team works across the globe, and we thrive in the autonomy and innovation of a startup environment. Here, people rally around a shared vision, advance quickly, and enjoy a fast-paced, fun culture. We’ve been making strides since 2019, and we’re always looking for people who will make us even better.

About the Role:

Join DearDoc's leadership team as the Head of Customer Success, driving customer retention, revenue growth, and a customer-first culture. Lead a high-performing team, implement strategic initiatives, and collaborate across departments to deliver measurable results in a fast-paced, innovative environment.

Location: [TBD - New York Preference]

Compensation: Commensurate with Experience

Benefits:

• Unlimited PTO
• Monthly Happy Hours
• Weekly Lunches
• Wellness Benefits
• Commuter Benefits
• CitiBike Membership
• HealthAdvocate Services
• Teladoc Services
• 3 Months Fully Paid Maternity/Paternity Leave
• Free Mental Health Benefits
• Medical, Dental, Vision, 401(k) Match
• 11 Paid Holidays

Essential Functions & Responsibilities:

• Drive customer success outcomes by increasing our 13-month logo retention rate by 35% over three years and doubling expansion revenue in the same period.
• Implement and enhance a customer engagement framework to identify at-risk accounts early and apply personalized strategies to reinforce value.
• Collaborate with sales and product teams to create targeted upsell opportunities that align with customer goals.
• Execute and scale proactive customer success programs, including onboarding, education, and engagement initiatives, to drive retention and expansion.
• Use data-driven insights to anticipate customer needs and deliver proactive support.
• Recruit, mentor, and retain a high-performing CS team focused on customer results and measurable impact.
• Champion a customer-first culture across departments to ensure every customer interaction reflects our commitment to their success.
• Own department metrics such as Customer Retention, Revenue Expansion, Customer Time to Results, and Customer Results Achievement, with regular monitoring and improvement.

Skills & Background:

• Minimum of 8 years of professional experience, with at least 4 years in a senior Customer Success or Sales leadership role within a SaaS or technology-driven environment.
• Aggressive drive to move quickly and effectively, while remaining approachable and results-oriented.
• Strong follow-through on commitments, with a proactive mindset for anticipating challenges.
• Proven ability to source and develop top talent, coaching team members for current and future roles.
• Flexibility to adapt quickly in a dynamic startup environment, maintaining a high standard of performance.
• Excellent strategic thinking skills, with the ability to make quick, informed decisions that support team objectives.
• Demonstrated enthusiasm, strong work ethic, and efficiency in achieving significant output with minimal wasted effort.
• Outstanding leadership and influence, inspiring team members to exceed goals and uphold high standards.

DearDoc, Inc. is proud to be an Equal Employment Opportunity and Affirmative Action employer. We do not discriminate based upon race, religion, color, national origin, gender, sexual orientation, gender identity, age, veteran status, or disability. Employment decisions are based on qualifications, merit, and business needs.

We do our best to respond to all applications as quickly as possible. We look forward to reviewing your background and connecting shortly to learn more about you! In the meantime….CHECK US OUT!

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