Technical Support Specialist

About MacStadium
MacStadium is the leading provider of enterprise-class Apple Mac infrastructure. Our Orka platform enables developers and DevOps teams to orchestrate macOS and Apple silicon in the cloud for CI/CD, testing, and development at scale. We serve some of the world's largest companies and are investing heavily in our platform for the future.
We are a remote-first company with a global team. We value autonomy, curiosity, and a bias toward action. If you want to have outsized impact on a small team building the future of Apple cloud infrastructure, we would love to hear from you.

About the Role
MacStadium's customer base and product portfolio are growing. Overall support volume is increasing. We are investing in the support team to stay ahead of that growth — adding a Tier 1 Support Specialist to continue delivering a best-in-class support experience for our amazing customers. You will act the human counterpart to MacStadium's new Tier 1 AI agent. The AI handles first-touch responses and the high-volume, low-complexity ticket flow. You own the rest: triage oversight for the AI agent, ticket lifecycle from new through solved, every escalation that goes to Orka development, platform engineering or product, and a defined set of Tier 1 software processes that customers depend on.

What You Will Do

• Triage and ticket lifecycle: Every support ticket has a clear owner, priority, and next action. While the AI agent will deliver an instant response for most customer questions, there may be some that require a human touch. We've developed a set of routing rules to efficiently drive towards customer resolutions. You keep the queue healthy — no stale tickets, no orphaned threads, no customer waiting longer than the SLA without an update.
• Escalations: When a ticket can't be resolved at Tier 1, you package it for the next team with full context: reproduction steps, customer impact, what's already been tried, and links to related tickets. You stay the customer-facing point of contact through resolution so the rest of the team can focus on the fix.
• Apple Business Manager (ABM) and MDM enrollment: End-to-end ownership of ABM and MDM onboarding for new customers and ongoing enrollment work for existing fleets. Public-key exchange, serial assignment, MDM profile pushes, troubleshooting enrollment failures, and partnering with the customer's IT team when they're new to ABM.
• SSO support: SAML/OIDC onboarding for new customers (Okta, Entra, Google, JumpCloud), troubleshooting authentication failures, and proactive management of SSO certificate renewals.
• Working with the Tier 1 AI agent: You're the quality bar for the AI's responses: reviewing its drafts when it flags low confidence, retraining it when it gets a recurring case wrong, and writing the knowledge base articles it draws from. You're the reason the AI gets smarter every quarter.

• Additionally you will:

  • Partner with the existing US and EU support team to maintain follow-the-sun coverage, share knowledge, and develop shared runbooks and troubleshooting guides

  • Help shape the AI support agent's effectiveness — reviewing its output, identifying gaps, tuning responses, and ensuring quality as it handles Tier 1 volume

  • Collaborate with the Head of Support on process improvements, knowledge base development, and operational metrics

  • Contribute to internal documentation, including root cause analysis write-ups, known issue tracking, and customer-facing KB articles

  • Act as a voice of the customer internally, surfacing recurring issues and feature requests to the product and engineering teams

What We Are Looking For
Required:

• 1–3 years in technical customer support, help desk, IT support, or a similar role
• Comfortable in Zendesk (or a peer ticketing system) and confident triaging a queue without hand-holding
• Excellent written communication: you can explain complex technical issues clearly to both engineers and non-technical stakeholders, and you document what you learn
• AI Native. Comfortable working with AI tooling as a collaborator and productivity accelerator
• Demonstrated ability to manage a ticket queue or support workflow — you know how to prioritize, triage, and keep things moving without dropping balls
• Based in the US with availability during standard US business hours (Eastern or Central preferred)
• Self-directed and comfortable working autonomously on a small, distributed team

Preferred:

• Working knowledge of at least one identity provider (Okta, Entra ID, Google Workspace, JumpCloud) and the basics of SAML and OIDC
• Familiar with Apple's enterprise tooling — Apple Business Manager, MDM concepts (Jamf, Kandji, Mosyle, or similar), and how Apple device enrollment works in practice
• Experience supporting a SaaS or infrastructure product
• Exposure to Mac infrastructure, Orka, VDI, and CI/CD pipelines
• Familiarity with Confluence, Slack, and modern dev/ops collaboration tools
• Basic networking: VPN concepts, certificates

What Success Looks Like

• Within 30 days: Owning the Tier 1 ticket queue, triaging and resolving Tier 1 tickets.
• Within 60 days: Handling implementations for ABM/MDM and SSO. Contributing to the internal and external knowledge base. Actively shaping the AI agent's Tier 1 output quality.
• Within 90 days: Fully operational — Tier 1 queue runs smoothly under your ownership.

What we offer

Competitive base salary, comprehensive health benefits, 401(k) match, generous PTO, remote-first culture, and access and training on leading edge AI tools.

Compensation Range: $55,000 - $71,000

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MacStadium has a defined Information Security Policy and all employees are required to adhere to this policy and sign an acknowledgment and receipt of this policy upon hire.

All offers of employment are conditioned upon successful completion of a background screening process and all employees must comply with the immigration rules and laws in the jurisdiction in which he/she/they will provide MacStadium services.

MacStadium is an Equal Opportunity Employer. All applicants are considered without regard to race, color, ancestry, national origin, gender/gender identity, sexual orientation, marital and family status, religion and religious belief, age, disability, results of genetic information, and service in the military.

Studies have shown that women and people of color are less likely to apply for jobs unless they believe they can perform every job description task. We are most interested in finding the best candidate for the job, and that candidate may come from a less traditional background. MacStadium may consider an equivalent combination of knowledge, skills, education, and experience to meet minimum qualifications. If you are interested in applying, we encourage you to think broadly about your background and skill set for the role.

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No recruiting agencies please.