Jessica Wolf Troublemaker at Skye

In December 2019, Harvard Business Review published a great article by Herminia Ibarra and Anne Scoular on changes for corporate managers. Up until 2020 and beyond, Ibarra and Scoular noticed things began to change:

As a manager, you knew what needed to be done, you taught others how to do it, and you evaluated their performance. Command and control was the name of the game, and your goal was to direct and develop employees who understood how the business worked and were able to reproduce its previous successes.

Rapid, constant, and disruptive change is now the norm. Twenty-first-century managers simply don’t (and can’t!) have all the right answers. To cope with this new reality, companies are moving away from traditional command-and-control practices and toward something very different: a model in which managers give support and guidance rather than instruction.  Source:

I know Jessica Wolf, CEO & Co-Founder of Skye, will see the opportunity in that Harvard Business Review article. As you’ll hear in my setup of the interview, the United Kingdom and the United States spend the least on online training, business, or life coaching.

Combining the paragraphs above, Jessica and Skye are in the right place at the right time.

Forbes 30 Under 30

For someone so accomplished at such an early age, Jessica is down to earth. Early in our interview she glossed over being highlighted in Forbes 30 Under 30. At the time she achieved that honor, she was Executive Director of Community at Forbes.

Jessica’s journey began when she and some friends were looking for a coach. It was difficult to find a good fit – chemistry fit, quality fit, pricing alignment, etc. The sector was decentralized and fragmented. There were manual and concierge approaches, but no world-class solutions at scale. Skye made it possible to bring coaches and clients together on one platform.

Once that model was working, Skye noticed that coaches – like many small business people – have difficulty managing their businesses. So they solved that right on the Skye platform.

On their website, The Skye Method lays out their 7-part methodology. It’s the entryway for new clients to join. It’s logical, clear, and a thorough process.

On the horizon

As you listen to Jessica’s interview, it’s very clear she is listening closely to their audience. That sort of approach inspired them to begin to explore a new idea – standardized learning journeys. These will be a less like coaching and more like pre-programed knowledge experiences.


Skye received $1.6M from Day One Ventures in July 2022. Source:
LinkedIn shows 24 employees
Based in New York City

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