Technology Services Engineer II

Full-time | Seattle

Hello we’re Accolade.

We have an opportunity to change the way consumers experience the healthcare system that’s really not working in their favor. Our mission is to make life better for the consumer, drive costs down for the business, and actually make people healthier through compassion, expertise, and technology.

Job Details

Accolade provides personalized health and benefits solutions designed to empower every person to live their healthiest life. We help millions of people and their employers navigate the complexities of the healthcare system with empathy, expertise and through exceptional service while supporting them in lowering the cost of care and improving health outcomes. Accolade blends technology-enabled health and benefits solutions, specialized support from Accolade Health Assistants® and Clinicians and access to expert medical opinion services for high-cost treatment decisions. We consistently receive consumer satisfaction ratings over 90 percent and have been recognized by Inc. Magazine as a Top Place to Work 2020 and Business Intelligence for Excellence in Customer Service 2020. Please visit us on LinkedIn, Twitter, Instagram and Facebook and at

Role overview

The Technology Services Engineer II will be responsible for providing desk side support and infrastructure services for our staff (Executive, Software Developers, Sales, Healthcare Assistants) as well as performing Windows server operations tasks. The Desktop environment includes Windows, Mac, and other computing platforms. This role is responsible for Accolade’s Windows servers.  Accolade is poised for aggressive growth, and this role will be a key element in maintaining current operations while expanding both our reach and our service offerings. Day-to-day, you will be coordinating your work with our Service Desk and the rest of the Infrastructure team, as well as working interactively with other Accolade staff.

A day in the life…

  • Provide full desktop service to staff at local our offices, both in-person and remotely, focused on Windows and Mac hardware and software, coupled with some networking.
  • Work with individuals with a wide range of computer skills, specifically when communicating technical information to nontechnical staff.
  • Maintenance and problem solving with respect to workstations and desktop applications.
  • Perform maintenance tasks on Windows servers
  • Effectively communicate technical information clearly and concisely to senior level technical staff during escalations.
  • Train and educate Service Desk and Infrastructure team members, sharing knowledge of new techniques and technologies.
  • Develop solutions to a variety of problems of moderate scope and complexity. 
  • Refer to policies and practices for guidance.
  • Act as second-level support escalation contact from front-line support or other desktop engineers.
  • On a regular, but varied basis, you will execute the new hire on-boarding process, support our development and training centers, perform server maintenance tasks, and design and develop implement and support the underlying infrastructure that provides services to all of Accolade’s users.

What we are looking for…

  • Bachelor’s degree in Computer Science, Information Management or related field and a minimum of 2 years related experience, or Associate’s degree and equivalent experience
  • Experience working in a Corporate Help Desk environment. This should include hands-on experience troubleshooting Mac OS X, Microsoft Windows 10, and Microsoft O365 for both Windows and Mac OS X environments, networking, Active Directory integration, and support of tele-collaboration tools such as Teams, Zoom, Slack.
  • Some experience with Windows Server maintenance.
  • Significant experience with tools and processes involved in new build automation and application deployment or management for Windows and/or Mac systems.
  • Experience with scripting and automation tools such as PowerShell, VBScript, batch files, or similar environments.
  • Experience automating software application installation and delivery, preferably in both Windows and Mac environments.
  • Experience working with mobile devices running iOS and Android operating systems.
  • Working knowledge of basic networking technologies, e.g. VLANs, DHCP, and DNS Servers.
  • Experience configuring and using audio/video conferencing tools like Zoom or WebEx.
  • Provide outstanding customer service face to face and via tele-support options, e.g. video, phone, email, text, etc.
  • Excellent problem solving skills.
  • In addition to providing white-glove support, should be able to synthesize support experiences to find or create the tools and processes needed to help scale this function, making yourself and the team more effective.
  • Works well with individuals at all levels; has a high enough EQ to engage successfully with people from a wide range of work backgrounds.
  • Ability to multi-task, think on your feet, and creatively solve problems.
  • Rigorous in your approach to work (Organized, dependable, metrics focused, agile, and have a high attention to detail).
  • Excellent interpersonal and communication skills with your peers and clients
All your information will be kept confidential according to EEO guidelines.
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Technology Services Engineer II

Product & Tech