Note: The job is a remote job and is open to candidates in USA. Sidekick Health is a global pioneer in digital health and therapeutics committed to transforming patient-centered care through innovative solutions. As a Technical Customer Success Manager, you will manage customer relationships, lead technical conversations, and drive automation to enhance operational efficiency.
Responsibilities
- Own and operate Sidekick’s service desk for customers and strategic partners, managing all inbound requests via Zendesk from line-of-business leaders, Care Managers, Care Navigators, members and others
- Triage, prioritize, and resolve issues directly where possible; route to the appropriate internal teams with clear context when escalation is required
- Own all follow-up and follow-through, ensuring timely resolution independently or in close collaboration with Customer Success
- Identify patterns in incoming requests and proactively suggest improvements to reduce repeat issues, improve customer experience, and make operations more scalable
- Act as the customer-facing subject matter expert on Sidekick’s platform, programs, integrations, and technical capabilities, leading technical conversations without requiring CTO involvement
- Quickly build trust and confidence with customers by demonstrating strong command of our platform, capabilities, and product roadmap
- Represent Sidekick in customer calls, confidently handling product questions, integration requirements, security inquiries, and root-cause analysis
- Collaborate with Product, Technology, and Delivery teams to translate customer feedback and issues into clearly scoped internal tasks
- Use sound judgment and critical thinking to challenge unclear requirements, identify risks early, and push for practical, scalable solutions
- Design and deploy automation systems and AI-enabled workflows to reduce manual effort, improve response speed, and enable scalable operations
- Build and iterate on agents and automation tools to handle high-volume, repeatable service desk tasks and reduce reliance on manual processes
- Lead the next phase of transformation by automating and digitizing customer-facing capabilities to improve experience, efficiency, and scalability
- Proactively identify where automation, AI, or process redesign can improve the way we work, rather than waiting for solutions to be handed over
- Serve as the link between Customer Success, Product, and Technology Delivery for all customer-related delivery matters and priorities
- Ensure clarity of ownership, priorities, and timelines across internal workstreams to support efficient execution
- Maintain accurate documentation, decision logs, and process records to ensure continuity and support organizational learning
- Operate with a high degree of independence, while knowing when to escalate, align, or bring the right stakeholders into the conversation
Skills
- 4–7 years of experience in a technical, customer-facing role in health tech or a similarly complex environment
- Demonstrated hands-on experience with AI tools, automation platforms, or agent-based workflows, not familiarity in concept, but practical application
- Ability to understand and communicate complex technical information including integration requirements, information security constraints, and product limitations to both technical and non-technical audiences
- Proficiency with service desk and project management platforms (e.g., Zendesk, Jira, Asana, Monday.com)
- Excellent collaboration and stakeholder communication skills
- Strong organizational skills and attention to detail, with the ability to manage multiple open workstreams simultaneously
- Bachelor's degree required; PMP, Scrum Master, or Agile certification a plus
- Genuine respect for the healthcare regulatory environment and an understanding of why compliance and data security are non-negotiable
- You bring energy and personality to the work, high-performing and fun are not mutually exclusive to you, and the teams and customers around you feel that
- Located and authorized to work in the United. Preference for candidates in Minneapolis, MN
- Familiarity with payer operations, care management workflows, or value-based care models
- Experience working with or supporting B2B Customer Success or Account Management teams
- Knowledge of compliance and SLA frameworks in regulated partner environments
- Familiarity with prescription digital therapeutics (DTx) or regulated digital health solutions
Benefits
- 401k match
- Health insurance
- Generous PTO
- Top technology
- Flexible working hours
- Access to Sidekick health programs
Company Overview