Job Description

Headway's mission is a big one - to build a new mental health care system everyone can access. We've built technology that helps people find great therapists with the first software-enabled national network of providers accepting insurance.
1 in 4 people in the US have a treatable mental health condition, but the majority of providers don't accept insurance, making therapy too expensive for most people. Headway is building a new mental healthcare system that everyone can access by making it easy for therapists to accept insurance and scale their practice.
Headway was founded in 2019. Since then, we've grown into a diverse, national network of over 60,000 mental healthcare providers across all 50 states who run their practice on our software and have served over 1 million patients. We're a Series D company with over $325m in funding from a16z (Andreessen Horowitz), Accel, GV (formerly Google Ventures), Spark Capital, Thrive Capital, Forerunner Ventures and Health Care Service Corporation.
We want your time here to be the most meaningful experience of your career. Join us, and help change mental healthcare for the better.
About the role:
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 will love this role if...

• 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.
• You enjoy having a mix of remote and in-person work and building relationships with on-site teams.

What you'll do here:

• Act as a senior technical resource within IT Support, owning and resolving complex issues, guiding incident resolution, improving processes, and setting a high standard for partnership and service excellence.
• Provide white-glove, high-touch support for executives and senior leaders, both remotely and on-site
• Oversee on-site A/V support for meetings, presentations, and company-wide gatherings ensuring seamless operation of video conferencing and presentation equipment in our NYC office.
• Support and maintain office infrastructure, including setup, configuration, and basic maintenance of network connectivity in our NYC office.
• Partner with IT Engineering to improve systems, tools, and processes that enhance the overall employee technology experience.
• Contribute to, maintain, and improve internal IT documentation and knowledge bases.
• Provide mentorship and serve as an escalation point for junior IT team members, sharing knowledge and fostering a culture of excellence.

You'd be a great fit if...

• 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 New York City 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.

Our interview process
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.
• Take Home Exercise: You'll complete a short (

1 hour) take home exercise. * 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 $146,000 - $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

#LI-EM1
We believe a team's strength is in its people, and we cannot achieve this mission without a team that reflects the diversity of this problem - across race, ethnicity, gender, sexuality, age, national origin, religion, family status, disability, military status, and experience.
Headway is committed to the full inclusion of all qualified individuals. As part of this commitment, Headway will ensure that persons with disabilities are provided with reasonable accommodations. If reasonable accommodation is needed to participate in the job application or interview process, to perform essential job functions, and/or receive other benefits and privileges of employment, please inform the recruiter when they contact you to schedule your interview.
Headway employees work remotely across the US, with the option to work from offices in New York City, San Francisco and Seattle. Headway participates in E-Verify. To learn more, click

Skills Required