About the Role:
We're looking for a Cloud Support Engineer to take ownership of our Microsoft 365 and Azure environments as we complete a major cloud migration and move into steady-state operations.
This is a high-autonomy role in a small, agile IT team. You'll be the internal subject matter expert for our cloud platform — managing identity, messaging, endpoints, and infrastructure — while driving cost optimization and automation across the organization. You'll mentor teammates, lead Salesforce production deployments, and set the technical direction for how we manage and scale our Microsoft ecosystem.
If you thrive with real ownership and want your decisions to matter, this is the role.
What you'll own
Cloud platform & identity
- Own Exchange Online, Teams, SharePoint, and M365 tenant policy, including licensing, mailbox management, and group provisioning.
- Administer Entra ID and Active Directory: Conditional Access, user lifecycle, domain controller decommissioning, M365 group management, and Azure RBAC across subscriptions.
- Manage resources across multiple Azure subscriptions (governance, networking, security, capacity). Administer Azure Files with a view toward eventual SharePoint migration.
Automation & workflows
- Build and maintain PowerShell and Python automation via Microsoft Graph API to reduce manual toil across M365, Entra ID, and Azure.
- Own the reliability and evolution of Power Automate flows supporting business operations, including the employee onboarding workflow.
Operations
- Execute production Salesforce deployments as the IT Operations rep. Per separation of duties, IT ops runs the deployment; engineering handles the code.
- Administer Mac endpoints via JAMF and Windows devices via Intune. Maintain policy compliance, software deployment, and consistent end-user experience.
- Own Azure cost management, M365 license rightsizing, and the ongoing reduction of Google Workspace licensing as users migrate to free-tier accounts.
- Support GWS administration during wind-down, including Chrome Browser Cloud Management for the organization's Chrome fleet.
- Rotating on-call (~1 week per 5–6 weeks). Escalation point for complex issues spanning identity, infrastructure, networking, and endpoints.
Team & operations
- Maintain runbooks and technical documentation that enable team scalability and preserve institutional knowledge.
- Guide IT team members on cloud platforms, automation, and operational practices. Not a people-management role.
- Own IT vendor and SaaS provider relationships, including contract oversight, renewals, and escalations.
What you’ll need:
- Minimum of 5–7+ years in IT or infrastructure with a strong focus on Microsoft cloud (Azure, M365, and related services)
- Deep hands-on M365 administration experience: Exchange Online, Teams, SharePoint, Intune, and Entra ID
- Solid understanding of on-premises Active Directory, including domain controller management and decommissioning
- PowerShell and/or Python scripting for automation, with comfort using the Microsoft Graph API
- Power Automate experience — building, maintaining, and extending automated workflows
- Familiarity with dynamic and static M365 group management and Azure RBAC role assignments
- Azure infrastructure experience: cost management, resource governance, networking fundamentals, and security posture
- Experience with structured release management or Salesforce deployment processes
- Strong troubleshooting skills across identity, infrastructure, endpoints, and networking layers
- Comfortable working independently on complex, ambiguous problems with minimal day-to-day direction
- Clear communicator who can translate technical context for non-technical stakeholders at any level
- Bachelor's degree in computer science, Information Systems, or a related field — or equivalent practical experience
Compensation, Benefits, & Additional Details:
Health-E Commerce's compensation philosophy is grounded in market data and internal equity to ensure fairness and consistency across the team. Individuals new to the company should generally expect offers to fall between the entry point and midpoint of the salary range. Our goal is to provide an offer that supports growth potential within the role and allows for future salary progression.
- Compensation: $120,000 - $150,000
- Discretionary Annual Bonus Eligibility: Up to 10%
- Medical, Dental, Vision, and 401K with a company match
- Dependent Care, FSA & HSA accounts
- Paid Parental & Bonding Leave
- Flexible PTO & office closure on all major holidays
- Monthly wellness & internet reimbursements
- Professional development including certification support & leadership coaching
- Mental Health resources
- 100% remote within the United States
- Must be able to work EST hours
Candidate Privacy Notice
Skills Required
- Minimum of 5-7+ years in IT or infrastructure with a strong focus on Microsoft cloud
- Deep hands-on M365 administration experience: Exchange Online, Teams, SharePoint, Intune, and Entra ID
- Strong troubleshooting skills across identity, infrastructure, endpoints, and networking layers
- Bachelor's degree in computer science, Information Systems, or a related field
What We Do
Health-E Commerce is a consumer health and wellness online retailer, comprised of four brands — FSA Store, HSA Store, WellDeserved Health and Caring Mill. Since 2010, we have launched direct-to-consumer e-commerce brands aimed at simplifying the U.S. tax-free healthcare market and helping everyday Americans and companies benefit better from workplace benefits, wellness and health spending programs. We are passionate about helping consumers to improve their health and maximize their health savings through qualified shopping and education. Through our websites, eligibility lists, and content, we help consumers understand, manage, and use their benefits. We also advocate for the eligibility of important new product categories, such as OTC meds and feminine care, to increase the types of everyday products that are eligible.
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