Technical Customer Success Manager (m/f/x)

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

Requirements:

• 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