Your mission with us

As Customer Technology Lead at Sidekick Health, you will serve as the technical backbone of our US payer and employer customer relationships, owning the service desk, leading all 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.

You will work closely with Product, Technology Delivery, and Customer Success 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 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, shape direction, and drive smarter, more scalable ways of working.

You will report directly to the CTO and partner closely with the VP of Customer Success, playing a key role in how we support and grow our customer relationships.

Your responsibilities

Service Desk Ownership

• 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.

Technical Platform Leadership

• 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.

AI Automation & Innovation

• 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.

Cross-Functional Collaboration

• 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.

Your profile

Qualifications

• 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.

Bonus Qualifications

• 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.

Why us?

Our Culture

• Inclusion, belonging, flexibility, and growth are core to how we work.
• Everyone is encouraged to become the best version of themselves.
• Feeling valued and fulfilled at work should be the norm.
• Challenges are opportunities – both personal and professional growth are part of the journey.
• A healthy work-life balance is essential, not just a nice-to-have.
• Empathy and social sensitivity are qualities we actively look for in our team members.
• Diverse teams simply perform better – and we build with that in mind.
• We believe in getting to know each other on a personal level.
• Our goal is to make a meaningful, positive impact on the lives of others.

Contact information

Ms. Jeanine Metaschk