Top Companies Still Hiring — Headway

Sally Bolig
6 min readMay 7, 2020

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In my continued effort to help hiring companies and exceptional candidates to more efficiently find one another, I’ll now begin spotlighting Top Companies *Still* Hiring. Not only are all of these companies still actively hiring, they have not undergone any layoffs.

This first company to be featured is none-other than Headway! I interviewed Keshar Sheridan, who heads up Recruiting and Talent for Headway and who worked closely with her CEO to answer the following questions. To see which roles Headway is hiring for, please visit their Careers Page. To learn how they’ve navigated COVID-19 and why they’re an all around impeccable place to work, just keep reading!

COVID-19 had a unique impact on the business model there at Headway. It actually further solidified and bolstered your existing mission, while enabling the opportunity to focus more energy on additional initiatives that had previously been on the backburner. Could you shed some more light on that?

The COVID-19 pandemic has in fact further solidified Headway’s mission which is to provide quality, affordable, and transparent access to mental health services here in New York. The pandemic has really shed a light on the need for what we are doing. People are anxious, isolated, and there are a lot of unknowns regarding jobs and the economy; it is certainly a time of a lot of stress. It has been extremely rewarding to work for a company that is making a difference in people’s lives at a time when they need support the most.

The pandemic has also encouraged us to explore new initiatives that were previously on the backburner. Some of the different initiatives we have been able to explore include partnering with primary care providers to field mental health referrals, and partnering with enterprise companies, to utilize Headway for their mental health employee benefits.

Many candidates are hesitant to join seed-round startups given the current climate. However, for Headway in particular, COVID has created an even greater urgency around growth, bolstering importance for — and stability of — your offerings both throughout and post-pandemic. Could you share a bit more about that evolution?

As we have been looking to grow our team, we have seen a great deal of hesitancy around joining a smaller, seed stage startup. Headway is positioned extremely well in this climate. We have raised enough capital in our seed round where we have enough runway for the next 18–24 months. We have also demonstrated incredible product market fit in New York. We have over 750 providers on our platform, making us the largest group practice in the United States, and we facilitate over 5,000 appointments each month. Although we are smaller than some other startups in NYC, we are stable and growing. We also afford tremendous opportunity for professional and personal growth in every position we hire.

What have you been doing to keep your employees engaged and clients feeling supported during this time?

Transitioning from a fully in-office environment to being 100% remote was definitely a challenge. But our leadership team, coupled with our People/Talent Acquisition team, worked to ensure that we were still remaining connected even though we were physically separated. One of the most important factors we took into consideration was — of course — how to support the mental and emotional well-being of our employees during a challenging and stressful time. To that end, we offered Headway as an employee benefit. Headway has covered all the co-pays associated with seeing therapists, deliberately and clearly encouraging our employees to take care of their emotional and mental health.

Some of the other changes we made to make sure our employees stayed connected include chat roulette sessions twice a week, where employees are paired up with someone from the company to have a light coffee chat. We also started lottery lunches, where small groups of employees virtually sit down together for lunch and enhanced connectivity. Our Leadership team has also made a concerted effort to stay connected with their teams. Our CEO is meeting with employees every 2 weeks — with the goal of having met with everyone within 6 weeks’ time — to receive real-time feedback around how we can improve our remote offerings. Overall, we have made tremendous strides in finding ways to keep everyone connected and supported.

You mentioned that you’ve been particularly inspired by your providers during this time. Tell us a bit more about the encouraging developments you’ve seen occur.

I think any organization that is functioning in the healthcare space has been inspired by our healthcare workers who are stepping in to support patients during the pandemic, and Headway is no exception. We were inspired to see so many providers reach out to us inquiring around how they could increase their service offerings to patients. We saw a huge increase in demand for telemedicine services from our provider side, with so many therapists wanting to support their patients remotely and virtually as much as possible.

The current climate has actually allowed the opportunity for Headway employees to contribute in very meaningful ways to departments outside their own. In what ways have you seen this happen?

One of the best parts of working at Headway is being able to step outside of your role and do meaningful work that is not necessarily part of your job description. Although this is common for our culture, we have seen this happen on a more broad scale during the time of the pandemic. One example of this was actually specifically around my role. Although I run the talent acquisition department, I was able to leverage my personal network to help with our enterprise business development initiatives. Other employees were able to utilize their previous backgrounds and interests to jump into other business critical initiatives as well.

Recent events aside, why is your company such a wonderful place to work?

First and foremost is the mission. The size of the problem we’re trying to address in the US is a very large one. We’re uniquely positioned to do so. Access to quality, low-cost, mental health services is a huge issue for people. We don’t have much competition who are providing people the ability to do this as uniquely as we do. To be a part of a company that provides life-changing support to people is so rewarding.

We’re also at a very unique stage: we’ve demonstrated product-market fit in NY and we will be expanding explosively across the states this year. We’re also small enough that you contribute in a meaningful way, strategically and creatively solving complex business issues.

And last, but certainly not least, the people are wonderful. It’s collaborative and we’re very close-knit. You want friends at work? This is the place you have friends at work. We have a dodgeball league, we have bakeoffs, we’ve had a Happy Hour at our CEO’s home. We take a lot of pride in this.

If you are looking for a place where you can truly make a difference in people’s lives and work with talented people in an industry that is ripe for disruption, then Headway is the right place for you!

If your tech company is actively hiring, you have not experienced layoffs, and you’re interested in being featured, please fill out this Google Form. I’ll reach out directly.

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Sally Bolig

Helping people find fulfilling careers, and enabling organizations to tell their own employer stories.