DearDoc - Head of Customer Success

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.