Senior IT Support Specialist

As a Senior IT Support Specialist at Headway, you will be vital in supporting all employees from a technology perspective as they build the future of mental healthcare. You’ll work closely with peers across IT to deliver exceptional service across both remote and in-office environments, with a focus on executive support, A/V systems, and event readiness. You’ll also contribute to scaling IT processes, improving tools and documentation, and mentoring teammates to elevate how IT operates across the organization.

• You enjoy solving technical problems and helping others.
• You are passionate about technology and staying up-to-date with the latest trends.
• You thrive in a fast-paced startup environment and bring structure where there is ambiguity.
• You want hands-on experience with the latest technologies.
• You value both technical depth and great customer service.
• You enjoy collaborating closely with teammates and cross-functional partners.

• Serve as a senior technical resource within IT Support, independently owning and resolving complex technical challenges, driving process improvements, and setting a high standard for service excellence
• Provide white-glove, high-touch support for executives and senior leaders, both remotely and on-site
• Oversee on-site A/V and office technology support for meetings and presentations, ensuring seamless operation with minimal hands-on involvement.
• Support and maintain office infrastructure, including setup, configuration, and basic maintenance of network connectivity in our NYC office.
• Collaborate with IT Engineering to design, implement, and optimize systems, tools, and processes that meaningfully improve the employee technology experience, applying independent judgment and technical expertise.
• Contribute to, maintain, and improve internal IT documentation and knowledge bases.
• Provide strategic mentorship and serve as a technical escalation point for junior IT team members, sharing expertise and fostering a culture of technical excellence
• Continuously evaluate IT support processes and systems to identify opportunities for efficiency, scalability, and improved user experience.

• You have 5-7 years of experience in IT support, systems administration, or a related field.
• You are able to work on-site at our San Francisco office 2 days per week, with flexibility for additional on-site support as required.
• You have experience providing white-glove technical support to executives and leadership teams.
• You have deep expertise with conference room technology and A/V systems and a knack for resolving issues in a timely manner
• You have administration expertise with at least three of the following products: Okta, Google Workspace, Zoom, Slack, Atlassian Jira, Atlassian Confluence, and 1Password.
• You have a strong understanding of macOS, Windows, and ChromeOS operating systems
• You have strong problem-solving, analytical, and communication skills, with the ability to build trust across all levels of the organization.

After you apply to Headway, here are some details of what to expect during the interview process.

• Initial Screen: You’ll connect with someone in recruiting so you can learn more about the team, Headway’s mission and exciting growth, and we can get a better idea of your background.
• First Round: You'll meet with the IT Manager to discuss your previous experience, and do an initial technical screen.
• Final Rounds: You’ll meet several team members for technical and non-technical interviews, and leave with a fuller picture of what it’s like to work at Headway.
• References and the Offer: Our favorite part of the process! We'll send over all of the details, including specifics on employee equity, and congratulatory messages from excited future team members!

The expected base pay range for this position is $146,200 - $172,000, based on a variety of factors including qualifications, experience, and geographic location. In addition to base salary, this role may be eligible for performance-based variable compensation and an equity grant, depending on the position and level.

We are committed to offering a comprehensive and competitive total rewards package, including robust health and wellness benefits, retirement savings, and meaningful ownership opportunities through equity. Compensation decisions are made holistically, ensuring fairness and alignment with market benchmarks while recognizing individual contributions and potential.

• Benefits offered include:
• Equity compensation
• Medical, Dental, and Vision coverage
• HSA / FSA
• 401K
• Work-from-Home Stipend
• Therapy Reimbursement
• 16-week parental leave for eligible employees
• Carrot Fertility annual reimbursement and membership
• 13 paid holidays each year as well as a Holiday Break during the week between December 25th and December 31st
• Flexible PTO
• Employee Assistance Program (EAP)
• Training and professional development

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