Company Description

Trupanion is a leading provider of medical insurance for cats and dogs in North America. Our mission is to help loving, responsible pet owners budget and care for their pets. At Trupanion, we offer a collaborative, casual, and pet-friendly environment where everyone is encouraged to be themselves.

Job Description

US – Remote: This is a remote position open to candidates anywhere in the United States. Candidates based in the greater Seattle area will work a hybrid remote/in-office schedule from our casual, pet-friendly office at least 3 days a week (Tuesday, Wednesday, and Thursday).

The Microsoft Platform Engineer serves as the technical SME and solution owner for our Microsoft 365 E5 and endpoint management ecosystem. This role will own the design, implementation, optimization, administer, and operational maturity of Microsoft 365 Apps (Exchange, Teams, Defender, Purview, Insights etc.), Intune, SCCM, application catalog services, endpoint compliance, and cloud patch management.

The ideal candidate is a hands-on engineer who can operate as both an implementer and strategic solution provider. This person will help modernize endpoint management, improve application delivery, strengthen patch compliance, optimize Microsoft E5 capabilities, and create a better user experience across the organization. This role will work closely with Infrastructure, Service Desk, Security, Compliance, and business teams to deliver secure, scalable, and efficient Microsoft platform services.

Key Responsibilities

Microsoft 365 E5 Platform Ownership

Serve as the technical SME and principal engineer for Microsoft 365 E5 services, with a focus on core productivity and collaboration platforms.
Own the engineering, configuration, governance, and operational support of Microsoft Office applications, including Outlook, Teams, Word, Excel, PowerPoint, OneDrive, SharePoint, and related Microsoft 365 services.
Evaluate existing Microsoft 365 E5 capabilities and identify opportunities to improve adoption, security, automation, compliance, and cost efficiency.
Partner with business stakeholders to understand productivity needs and translate them into secure, scalable Microsoft platform solutions.
Develop standards, best practices, and platform governance for Microsoft 365 service configuration and usage.
Act as an advocate for Microsoft 365 capabilities by educating teams on available tools, features, and productivity opportunities.

Endpoint Management: SCCM, Intune, and Co-Management

Engineer, administer, and optimize Microsoft Intune and Microsoft Configuration Manager/SCCM environments.
Lead endpoint management modernization efforts, including migration from traditional SCCM-heavy models to cloud-first or co-managed endpoint strategies.
Design and manage device compliance policies, configuration profiles, security baselines, endpoint restrictions, and conditional access integrations.
Develop and maintain Windows device enrollment, provisioning, Autopilot, and lifecycle management processes.
Manage endpoint standards for corporate devices, virtual desktops, remote users, and shared workstations.
Ensure endpoint management practices align with security, compliance, audit, and operational support requirements.
Provide Tier 3/engineering-level support for endpoint management escalations.

Application Packaging, Deployment, and App Catalog

Own the enterprise application catalog strategy for Microsoft-managed endpoints.
Package, test, deploy, and maintain business applications through Intune, SCCM, Company Portal, and other approved distribution mechanisms.
Develop application deployment standards, including detection rules, dependency management, rollback procedures, and user communication processes.
Partner with Service Desk and Application Support teams to ensure cataloged applications are current, accurate, supportable, and easy for users to access.
Establish repeatable intake, testing, approval, and publishing processes for new applications.
Monitor application deployment success rates, failures, remediation actions, and user adoption.
Identify opportunities to reduce manual installs, improve self-service, and streamline application lifecycle management.

Cloud Patch Management and Endpoint Security Operations

Design and implement modern patch management strategies using Intune, Windows Update for Business, Autopatch, SCCM, and related Microsoft technologies.
Own patch compliance reporting, exception handling, deployment rings, maintenance windows, and remediation workflows.
Partner with Security and Infrastructure teams to ensure timely remediation of vulnerabilities across Windows endpoints and Microsoft-managed devices.
Develop patching dashboards, compliance metrics, and executive-ready reporting for endpoint health.
Create controlled deployment strategies for OS updates, feature updates, driver updates, firmware updates, and third-party application updates where applicable.
Continuously improve patch success rates, reduce endpoint risk, and minimize disruption to end users.

Solution Engineering and Platform Improvement

Serve as a solution provider for business and IT teams by designing practical, scalable Microsoft-based solutions.
Lead technical discovery, requirements gathering, design, implementation, testing, rollout, and operational handoff for Microsoft platform initiatives.
Evaluate current-state tools, processes, and configurations to identify gaps, risks, inefficiencies, and opportunities for standardization.
Create technical roadmaps for Microsoft platform maturity, including endpoint modernization, application lifecycle automation, and user productivity enhancements.
Develop proof-of-concepts and pilots for new Microsoft capabilities before enterprise rollout.
Partner with Security, Compliance, and IT leadership to align Microsoft platform initiatives with enterprise risk and governance requirements.
Contribute to cost optimization by improving license utilization, eliminating duplicate tools, and maximizing existing Microsoft E5 investments.

Documentation, Governance, and Operational Excellence

Create and maintain technical documentation, runbooks, support guides, architecture diagrams, SOPs, and knowledge base articles.
Define clear operational handoffs between Engineering, Service Desk, Security, and Application Support teams.
Establish governance for Microsoft 365 configuration changes, endpoint policy updates, application catalog publishing, and patch deployment.
Participate in change management/CAB processes for production-impacting Microsoft platform changes.
Define success metrics and regularly report on platform health, adoption, compliance, and operational performance.
Mentor Service Desk and junior engineers on Microsoft platform support practices.
Drive continuous improvement using measurable outcomes, operational data, and user feedback.

Required Skills

Microsoft 365 and E5 Platform Expertise

Strong hands-on experience with Microsoft 365 E5 services and administration.
Deep understanding of Office desktop applications, Teams, Outlook, OneDrive, SharePoint, Exchange Online, Copilot, Defender, Purview, Insights and Microsoft 365 Apps for Enterprise.
Experience with Microsoft 365 Admin Center, Endpoint Manager Admin Center, Entra ID, and related admin portals.
Ability to configure, support, and troubleshoot Microsoft productivity platforms in an enterprise environment.
Understanding of Microsoft licensing concepts, especially E5 capability differences and optimization opportunities.

Endpoint Management Skills

Advanced experience with Microsoft Intune.
Advanced experience with Microsoft Configuration Manager/SCCM.
Strong understanding of co-management, cloud attach, device collections, deployment rings, compliance policies, and configuration profiles.
Experience with Windows Autopilot, Windows enrollment, device provisioning, and endpoint lifecycle management.
Experience managing Windows 11 enterprise endpoints.
Ability to troubleshoot endpoint policy application, device compliance, enrollment failures, deployment issues, and configuration drift.

Application Packaging and Deployment

Experience packaging and deploying applications using Intune and SCCM.
Knowledge of MSI, EXE, Win32 app packaging, PowerShell-based deployments, detection rules, dependencies, superdense, and uninstall logic.
Experience managing self-service app catalogs through Company Portal or similar enterprise portals.
Ability to standardize software deployment processes and improve app delivery reliability.
Experience with application testing, rollback planning, and production deployment governance.

Patch Management and Security Alignment

Strong knowledge of Windows Update for Business, Intune update rings, feature update policies, quality updates, and driver management.
Experience with SCCM software updates, ADRs, patch collections, maintenance windows, and compliance reporting.
Understanding of vulnerability remediation workflows and endpoint security hygiene.
Ability to partner with Security teams to prioritize patching based on risk, severity, exploitability, and business impact.
Experience building patch compliance reports and operational dashboards.

Automation and Scripting

Strong PowerShell scripting skills for automation, reporting, troubleshooting, and endpoint remediation.
Experience using Microsoft Graph PowerShell or Graph API is highly preferred.
Ability to automate repetitive endpoint and Microsoft 365 administration tasks.
Familiarity with remediation scripts, proactive remediations, detection scripts, and configuration validation.
Understanding of JSON, CSV, REST APIs, and automation workflows is preferred.

Operational and Soft Skills

Strong analytical and troubleshooting skills.
Ability to work independently as a senior technical owner.
Strong documentation and communication skills.
Ability to explain technical concepts to both technical and non-technical audiences.
Strong customer-service mindset with focus on user experience.
Ability to balance security, usability, compliance, and operational efficiency.
Experience working in ITIL-based environments, including incident, problem, change, and request management.
Ability to mentor junior team members and influence peers without direct authority.

Qualifications

Required Qualifications

7+ years of IT infrastructure, endpoint engineering, or Microsoft platform experience.
5+ years of experience with Microsoft 365 administration.
5+ years of experience with SCCM/Microsoft Configuration Manager.
3+ years of experience with Microsoft Intune.
Strong experience with Windows endpoint management, Office applications, app packaging, and patching.
Strong PowerShell scripting and automation skills.
Experience with Windows Autopilot, Company Portal, update rings, compliance policies, and app deployment.
Strong troubleshooting, documentation, and stakeholder communication skills.

Preferred Qualifications

Microsoft 365 Certified: Endpoint Administrator Associate.
Experience with Entra ID, Defender for Endpoint, Conditional Access, Autopatch, and Microsoft Graph.
Experience with Power BI or other reporting tools.
Experience in ITIL, SOX, audit, or regulated environments.proofs-of-conceptadministration.

Additional Information

Compensation

The base salary range for this position is $145,000 - $155,000 on a full-time schedule.
Along with base compensation, Trupanion employees are currently eligible for monthly bonuses.
We want all employees to be invested in Trupanion’s success, so we grant Restricted Stock Units to all new team members. Our new hire grants vest over 4 years.

Benefits and Perks:

Full medical, dental, and vision benefits at no cost to the employee
Four weeks of paid time off and 9 paid float holidays (you can decide which days are most important to you!)
Five-week sabbatical after five years of employment
Open, casual, pet-friendly, and fun office environment
Free medical health insurance for your pet (1 dog or cat)
Paid time off to volunteer at nonprofit organizations
Seattle Office Amenities: Free on-site gym, free dog walking services for office pets during business hours, free parking, and paid ORCA cards.

For more information about Trupanion, visit https://trupanion.com/about

Learn more about how Trupanion has revolutionized our industry and the reimbursement model: https://www.youtube.com/watch?v=vdWZ4KHiPTQ

Trupanion is an equal-opportunity employer and embraces diversity. We are committed to building a team that represents a variety of backgrounds, abilities, perspectives, and skills.

We will ensure that individuals are provided reasonable accommodation to participate in the job application or interview process, perform essential job functions, and receive other benefits and privileges of employment. Please contact us to request accommodations.

Applicants must be authorized to work for any employer in the U.S. We are unable to sponsor or take over sponsorship of an employment visa at this time.

Department: Information Technology

Compensation: USD 145000 - USD 155000 - yearly