Coach Matchmaking

Jessica Wolf is the CEO and Co-Founder of Skye, a VC-backed SaaS-enabled platform in the executive coaching space. Featuring 100+ world-class coaches from Google, Lyft, BCG, Pinterest, McKinsey, etc., Skye propels individual and team performance, and partners with companies to strategically engage, train and upskill talent.

Before founding Skye, Jessica held various positions on the community side of renowned organizations such as Summit, Forbes, and ICONIQ Capital.?

Jessica is a community builder, coach, and startup leader trained at Dartmouth, Summit, Forbes, ICONIQ, and Columbia Business School. She dedicated her career to launching new communities and products across media, hospitality, and venture.?

Her entrepreneurial and community work has been featured in The New York Times, Forbes, Business Insider, Harpers Bazaar, La Republicca, and Protocol. She has been awarded Forbes U30 and Tribeca Disruptor.

#FridayFutures Highlight 31: Jessica Wolf, CEO & Co-Founder - Skye

What inspired your transition from community-building roles at various organizations to creating your coaching platform?

Community is crucial; it puts you at the intersection of what everyone desires and requires. Your role essentially involves finding ways, whether through marketing, events, sales - a combination of all three, to deliver a return on investment to the business. However, the ultimate goal is to help people achieve what they want, right?

For example, consider housing. People weren't merely seeking a desk and a chair for $1,500 a month; they were seeking the hope of finding a new business partner, securing financing, making friends, and, most importantly, being part of a community. They were paying for this sense of belonging. So, while we provided real estate, our focus was on fostering a sense of community.

This theme continued with Vivonne, where we sold apartments but presented them through the context of a dinner party, bringing people together. This perspective carried over into media, hospitality with Summit, and eventually, into Venture.

Community serves as a means of building brand awareness and delivering a softer message about what a company does and can offer. By being at the heart of these various communities, I've had the opportunity to meet numerous people and hear various perspectives. At the end of the day, I've come to recognize that, no matter how successful someone may appear on paper, everyone is looking for some form of support. Coaching addresses that need. I can delve further into why coaching specifically and the whitespace within this fragmented market, but it was my experience within these communities that allowed me to see the fundamental human need and how to fulfill it.

What’s your hot take or unpopular opinion about the future of coaching?

In the current landscape, AI and coaching are hot topics, with investors, coaching platforms, and users discussing their potential impact. AI is a prevalent conversation across various industries, and many believe it has the capacity to replace one-on-one human interactions, possibly even surpassing human coaches in accountability and the ability to measure effectiveness over time.

However, when it comes to coach engagement, I hold the view that AI will never fully replace the human connection. I remain optimistic about the importance of personal, curated relationships built through coaching. While AI plays a crucial role and can enhance coaching efforts, I don't see it as a complete substitute.

Is there a person or company that inspires you right now?

I believe that the digital health space is currently experiencing a significant and meaningful moment. Consumers are gaining access to more affordable support, including therapy and coaching. Enterprise companies are also continuing to invest in supporting their team members with mental health and career advancement services, even amidst economic changes.

As for your question about specific companies, I can't provide a direct answer, but I believe that this trend will persist. Whether it's in a hybrid work environment, fully remote, or in the office, the rise of investing in oneself and one's team through digital health support will continue to grow.

Regarding my reading habits, I follow various newsletters. Lenny's newsletter is probably my favorite as it delves into the details of topics such as go-to-market strategies, hiring, and unit economics—ideal for a founder at my stage. I also appreciate Morning Brew for its strong HR Tech newsletter. HR Tech is our field, and HR professionals are our target audience, so staying informed about trends in that space is highly valuable. Additionally, I follow various daily news sources to stay up-to-date.

What advice do you have for someone looking to get started with coaching, especially if they're considering Skye, and how can individuals navigate the process of finding the right coach?

People often ask me if there's a right time to get a coach, or if they're too young for coaching. Some even express the need for coaching but are unsure about the specific areas they want to work on. Well, I don't believe there's ever a wrong time to engage a coach, but having clarity about your goals can lead to more meaningful outcomes.

Achieving this clarity often involves self-reflection and self-awareness. Some individuals might say, "I want a promotion" or "I'm looking for a new job," but these goals require a deeper understanding of one's strengths and weaknesses and a commitment to personal and professional development. Coaching goes beyond surface-level objectives; it involves introspection, self-understanding, and a willingness to put in the effort to grow.

Coaching isn't just about addressing problems; it's also about exploration, discovery, and gaining a deeper understanding of oneself. Even when life seems to be going really well, coaching can be a valuable tool for personal and professional growth, helping you become the best version of yourself, whether that's in your career or in other aspects of your life. It's about continuous improvement and striving for excellence.

How do you approach quick and effective matchmaking in the coaching space, particularly with Skye?

Our community of coaches operates on a referral basis. Initially, our coaches came into the fold through their relationships with me across my various careers. Subsequently, new coaches have joined us through referrals from our current coaching community. This has created a close-knit community of coaches who know each other well, share perspectives, learn together, and uphold a high standard of excellence.

This highly curated, referral-based approach is now scaled up to offer you, the consumer, a more accessible and simplified experience. Instead of relying on personal connections, we use a few key criteria such as personality, professional backgrounds, goals, aspirations, and price points to match you with the most suitable coach. We prioritize aligning your values with your coach's values. You'll receive three matches, allowing you to experience complementary introductory sessions with each coach. This way, you can assess the chemistry, quality, and fit for yourself and then make an informed choice.

We've found that our matches are often spot on, especially when you have three options to compare, trust, and help you narrow down what you're looking for. Additionally, you can read reviews on the coach's profiles, which function like referrals to provide further insights.

What’s the most exciting thing you’ve learned you’d want others to know?

It may not be the most exciting revelation, but I've had to grapple with separating my identity from what we were building. At first, I found it challenging because there was this pervasive notion that if the company failed, I failed. While there may be some truth to that, I've come to realize that it's essential to take my ego out of the equation when it comes to company building.

What I've learned from this shift in mindset has been invaluable. It's resulted in better leadership. Instead of succumbing to moments of chaos and anxiety that could negatively impact my team, I've been able to step back, assess situations calmly, provide clearer direction, and be a confidant to my team members. They can trust me, and I can better support them.

By resisting the chaotic startup culture fueled by ego, I've made significant strides in my growth. It's a journey, and I'm a work in progress, but it's been one of the most important lessons I've learned.

How do you manage the balance between sharing your personal journey and promoting Sky on platforms like LinkedIn, where your personal and professional worlds often intersect?

Even if I weren't running Skye, I would remain dedicated to personal and professional development, both for myself and for my broader community, including friends and professional acquaintances. This dedication stems from a genuine passion for growth and improvement, and it has been a common thread throughout my various roles and endeavors.

For instance, I co-run a female founder community with my friend Nicole Maffeo. This community is designed to support women by providing funding opportunities, sharing knowledge, fostering connections, and offering insights. While this may appear to be a blend of personal and professional interests, it illustrates that I would likely continue engaging in similar initiatives, whether or not Skye exists. It's a testament to my commitment to personal and community growth.

How can we stay in touch with you?

You can follow me on LinkedIn, where I regularly share anecdotes and insights about my experiences as a startup leader and in the coaching space.

If you're interested in Skye, you can visit our website. There, you can explore our impressive roster of coaches and even experience your first three complimentary coaching sessions. It's a great opportunity to get a taste of coaching and see if it resonates with you.

Have thoughts on this week’s topic or question for me or Jessica? Post your thoughts in the comment section. Until next week.??

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