Technical Customer Success Manager; m​/f​/x

Your mission with us

As Technical Customer Success Manager (m/f/x) at Sidekick Health, you will serve as the technical backbone of our US payer and employer customer relationships, owning the service desk, leading customer-facing technical conversations, and building trust in our platform, programs, and roadmap. You will also drive automation and AI-enabled capabilities to scale operations.

This is not a traditional Customer Success role and not a purely internal engineering role. We are looking for someone who can combine strong technical judgment with customer-facing communication, operational ownership, and a builder mindset.

You will work closely with Customer Success, Product, and Technology Delivery to resolve issues efficiently, answer technical questions with authority, and ensure delivery commitments are met while continuously improving how we operate at scale.

This role sits within the Customer Success organization and works alongside our commercial teams to support and grow our customer relationships. It starts with ownership of the service desk supporting US payers and strategic partners and will expand as we grow. You are expected not only to solve critical issues, but also to anticipate needs, question assumptions, shape direction, and drive smarter, more scalable ways of working.

Candidates must be based in the United States and able to work across U.S. time zones, from Eastern to Pacific. Preference will be given to candidates based in Minneapolis, MN, or remote candidates located in the Eastern Time Zone.

• 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 work streams 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 elevate, align, or bring the right stakeholders into the conversation.