This NYC-Based Career Coaching Startup Urges Job-Seekers to Aim for the ‘Skye’

Skye’s platform includes coaches that are current and former executives from big-name companies such as Google, Condé Nast and Lyft.

Written by Miranda Perez
Published on Aug. 23, 2022
This NYC-Based Career Coaching Startup Urges Job-Seekers to Aim for the ‘Skye’
Jessica Wolf sitting down smiling
Skye co-founder and CEO Jessica Wolf. | Image: Skye / Built In

Sure the latest initiatives from the Teslas, Apples and Googles of the industry tend to dominate the tech news space — and with good reason. Still, the tech titans aren’t the only ones bringing innovation to the sector.

In an effort to highlight up-and-coming startups, Built In has launched The Future 5 across 11 major U.S. tech hubs. Each quarter, we will feature five tech startups, nonprofits or entrepreneurs in each of these hubs who just might be working on the next big thing. You can check out last quarter’s NYC round-up here.

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When seeking out a new career move, people often look for guidance with a career coach and nearly half of workers find one through referrals and word of mouth. This process, according to Jessica Wolf, co-founder and CEO of Skye, can be extremely time consuming and tiring. 

Wolf experienced these emotions firsthand just a few years ago after dealing with a broken engagement and considering a cross-country job offer.

“I was looking for support to manage tremendous internal turmoil during that time, but found it nearly impossible to find a coach that could help cultivate clarity and strategy in my life,” Wolf told Built In via email. “The entire process of finding a coach was extremely challenging. I didn’t have the emotional capacity to tell my story over and over to a stranger only to find they weren’t good for my needs.”

It was then that Wolf joined forces with her co-founders to build Skye, a career coaching startup that connects individuals with qualified career counselors that can help them excel in their personal and professional lives.

Skye’s technology works to personalize the career coaching experience by analyzing candidates’ backgrounds to then match them to coaches that align with their aspirations and needs. 

Our brand hopes to evoke feelings of limitless potential, as in Skye’s the limit.”

Since launching earlier this year, Skye has pulled in $1.6 million in seed funding from Stellation Capital, Incite Ventures, Day One Ventures and other angel investors. 

Wolf told Built In that Skye has been using its capital to onboard more clients and coaches and build up its software infrastructure to better serve both aspects of its business. So far, the platform has hundreds of users and roughly 100 coaches that include current and former executives from big-name companies such as Google, Condé Nast and Lyft.

“A key reason that clients come to us is to find clarity in their career, whether they’re switching jobs, looking to transition or unsure what they’re doing next,” Wolf said. “Our brand hopes to evoke feelings of limitless potential, as in Skye’s the limit.”

Looking forward, Skye plans to hire another sales lead and potentially an engineer to continue building out its platform capabilities. 

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