This Startup Is The Secret Behind The Success Of Silicon Valley Leaders


What’s the secret behind a leader’s success? Almost every successful and high-performing individual including Bill Gates, Sheryl Sandberg, Marc Benioff, and Oprah Winfrey have had coaches. A search for “coaches” on LinkedIn brought in over 6.28 million results in 2020, and coaching and personal development is a $38B industry that’s continuing to grow.

Enter Skye, the platform that matches executives and leaders with a dedicated coach to accelerate their life and career. Clients include everyone from the Chief of Staff at First Round Capital, to the leadership team at Handshake ($3.5 billion company), to the C-suite at K Health ($1.5 billion company) and executives at Audible, Pepsi and Estee Lauder.

I interviewed Skye’s co-founder and CEO Jessica Wolf about her inspiration for starting a coaching company, how she’s navigating being a first-time founder during these turbulent times, how coaching helps leaders level up, and more.

Gary Drenik: Tell me a little bit about your founding story. Where was your inspiration behind starting a coaching platform?

Jessica Wolf: Skye was born out of a personal need. It all started when I was dealing with a broken engagement and a job offer across the country a few years ago. I was looking for support to manage the turmoil I was experiencing in my life, and started looking for a coach. But outside of Googling for coaches or asking friends for recommendations, I found it nearly impossible to find the coaching support that would help me level up personally and professionally. The entire process was challenging, and it was exhausting to tell my story over and over to a stranger only to find that they weren’t the best fit for my goals.

Coaching is a highly unregulated and decentralized industry, with few places to find vetted, curated coaches. We’re proud that Skye’s coaches have real-world executive leadership from Google, Dropbox, Lyft, Oscar Health, Sony, Conde Nast, Louis Vuitton and Quip. Our clients are startup founders and executives from companies such as Estee Lauder, First Round Capital, Blackstone, AmBev and more. Entrepreneurs even use Skye to find their first advisors. The Myers-Briggs Company and Columbia Biz School Behavioral Management professor are among our advisors.

Our matching algorithm has been an integral part of our success, allowing for automated and accurate coach and client matches based on inputs including professional background, goals and aspirations, personality and value systems.

Drenik: What types of support do executives and leaders seek on Skye?

Wolf: Executives and leaders find coaches on Skye to level up. They’re founders who want to be better leaders for their organizations. They’re building a sales organization and seek guidance from a coach who’s successfully done it before. They’ve just transitioned to a massive leadership role and are combating imposter syndrome. They want to unlock deep-rooted beliefs and break down their mental blocks.

According to a recent Prosper Insights & Analytics survey, around 40% of people anticipate there will be more layoffs in the next 6 months. They may be re-thinking their own career trajectory and planning ahead in case they might be affected, and coaching is especially relevant during turbulent times like the one we’re currently experiencing.

Drenik: Why do you think there’s an upward trend of more and more people seeking coaches?

Wolf: The past few years and turbulent times have caused deep questioning around purpose and enormous disruptions in the workforce, daily routines and overall lifestyle. People lack mental clarity around their personal and professional lives. We found that people come to Skye for the main four reasons below.

  • Personal growth: Coaches can help individuals identify their strengths, weaknesses, and areas for improvement, and develop a plan to achieve their goals.
  • Career advancement: Coaches can also help individuals navigate their careers and achieve professional success. They can provide guidance on how to develop skills, network, and advance within a particular industry.
  • Improved relationships: Coaches can also help individuals improve their relationships with others, whether it’s in their personal or professional lives. They can help individuals develop better communication skills, build trust, and establish healthy boundaries.
  • Accountability: Coaches can provide individuals with the accountability they need to achieve their goals. By setting specific goals and regularly checking in, coaches can help individuals stay on track and motivated.

Drenik: You started Skye in late 2021. You’ve been operating during times of highs and lows: through the pandemic, when record amounts of VC dollars were being raised in 2021, and now the recent tech layoffs. What are some trends you’ve seen throughout these times?

Wolf: Economic uncertainty affects more than just the health of a business, but the internal feelings of psychological safety. Leaders are acting in the best interest of their company, which can sometimes be at odds with people considerations. We’ve seen communication, transparency, and investment in L&D to be more important now than ever. As teams adjust to layoffs, salary cuts, and ultimately, a cultural shift in the tech workplace, ensuring your remaining leaders are supported is critical to the long term success of a company. At the end of the day, it’s all about people.

Drenik: As a first-time founder yourself, do you have your own coach? If so, how has your coach helped you run a business and lead a team during uncertain times?

Wolf: Yes, I have an executive coach and a life coach. My executive coach supports me both strategically and emotionally. As an early stage founder, I looked for fundraising and hiring support. Now that we’ve onboarded our enterprise sales team, I lean on my coach for best practices in sales management – how to motivate, and manage an enterprise team. It’s difficult to separate my identity from the business. My coach helps me regulate my emotions, manage the ups and downs, and therefore, be a more calm, transparent and communicative leader.

Drenik: Have you made any pivots to your business since launching it?

Wolf: We began as a consumer-first company. There was white space in the b2c coaching market – room for a tech-driven, community-led coaching platform that served leaders across all stages of their life and career. And frankly, I personally related more to the consumer problem. I had not intended to expand into enterprise so quickly but am glad we did! But we did so to answer our clients’ needs – they asked us to coach their teams at scale, and so we launched b2b to answer the call.

Drenik: Thank you, Jessica, for sharing more about Skye’s vision and how the company is elevating executives and leaders through coaching.

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