Read the 33-page pitch deck that career coaching startup Skye used to raise $1.6 million

Jessica Wolf, CEO and cofounder of coaching platform Skye.
  • Skye, a platform to find executive and life coaches, is launching to the public today.
  • The platform has tapped current and former execs from Google, Conde Nast, and Lyft as coaches.
  • Read the 33-page pitch deck the founders used to raise a $1.6 million pre-seed round in January.

The idea for coaching platform Skye, a marketplace to find life and executive coaches, came from a personal experience.  Three years ago, Jessica Wolf, Skye’s CEO and cofounder, spent months looking for a coach without success.

She was trying to break into venture capital, was considering moving across the country for a job offer, and couldn’t decide if business school was the right move. On top of it all, she was ending a relationship. 

But she couldn’t find the right person to advise her. Some existing coaching platforms, like BetterUp and Torch, targeted companies, not individuals. Meanwhile, Ginger, a platform for behavioral health coaching, didn’t provide the kind of career expertise she wanted.

“I thought ‘A therapist will not cut it because I need strategic career advice,'” Wolf told Insider. “I wanted someone who had a tenured background. I didn’t want the coach who graduated from college and just became a coach, or was a therapist for a few years and then switched over to coaching.”

In 2021, after two years of sitting with the idea, Wolf, who had decided she did want to get that MBA, teamed up with two fellow Columbia Business School students — CPO Tony Lin and CTO Gabriel Chen — to build a new coaching platform to fill the needs she had had years ago.

Today, Skye is home to nearly 100 coaches, including current and former executives from Google, Conde Nast, Lyft, Dropbox, Oscar Health, BCG, and Sony Entertainment, in addition to professional coaches. The platform, which launched to the public this month after nine months in beta, has hundreds of users.

Before they went to investors, the cofounders wanted to have a platform built out, as well as a solid roster coaches.

“We have to get coaches first,” Wolf said. “If we don’t have coaches, we can’t sell anything.”

She pulled from her own connections from the Columbia Business School alumni network, venture capital, and media.

These coaches are matched with clients through an algorithm. When joining, clients fill out a questionnaire about their background, goals, and growth areas, and the algorithm creates recommendations for coaches based on those answers, price point, values, and objectives.

Currently, coaches set their own prices for monthly subscriptions, and the platform takes 10% in fees.

New coaches have to be referred to Skye by current coaches, and they then go through a vetting process which includes an interview and a mini coaching session with the cofounders. 

Once a coach is on board, Skye connects them with clients and also serves as their CRM, with tools like contracting, calendar integration, video conferencing, billing, and goal tracking.

In early 2022 — after the platform had launched in beta, and brought on 50 coaches and over 200 clients — the company raised a pre-seed round of $1.6 million from Stellation Capital, Incite Ventures, Day One Ventures, and several angel investors. 

In order to hook investors, Wolf used a 33-page pitch deck that she put together in November 2021, when she began the pitching process. She updated it and tailored it to different investors during the three months she spent raising funds.

“I had two different versions, depending on the fund,” Wolf said. “If I knew a fund was more into pre-seed, all about the founder, I had one deck. But if I knew that they were a numbers person, I would use another one.”

The cofounders also included information they collected during calls with people in their network about coaching, including their needs and budgets.

“We were able to actually say ‘This is an average willingness to pay’ because we learned that, we’re not making it up,” Wolf said.

Read through Skye’s pitch deck that helped them raise their $1.6 pre-seed round:

The pitch deck opens with a presentation page.


The second page includes a concise description of the product.


The third page gives a definition of coaching, according to Skye, and how it combines and differs from consulting and therapy.


The slide reads:


A partnership that outlines a solution-oriented strategy for success.

It is a process that involves understanding where you are and where you aspire to be in an effort to co-design a behavioral and strategic roadmap to get you there. Coaching is a strategic approach to purpose and fulfillment. 

The next page defines the ROI of coaching and lists notable individuals who have received coaching.


This slide lists individuals who have had coaches, like Oprah Winfrey, Bill Clinton, and Serena Williams, and describes the “ROI” of coaching, which improves actionability by 91%, outlook by 94%, and learning by 88%.

It also includes some relevant quotes about coaching, like “Everyone needs a coach” from Bill Gates and “Best advice: find a coach” from former Google CEO Eric Schmidt.

Then, there are concrete examples of Skye clients and why they seek coaching.


There are also examples of Skye coaches and why they’re getting into mentoring.


The next page details how Skye’s technology works, both for coaches and for clients.


Then, it explains how the algorithm pairs coaches and clients, and includes a real example of a successful match.


Then, the deck goes into a brief history of how Skye grew before raising capital.


The slide reads:

What we’ve bootstrapped together, in a few short months.

Early September
Started onboarding coaches

Mid September
Manual matches delivered to 15 clients

Mid September
Pivoted to a monthly subscription model

Late September
Launched coach profiles and editing capabilities

Early October
Social media announcement & grassroots marketing

Early October
Launched calendar management and booking

Mid October
Forbes U30 & Soho House event series

Late October
Launched matching algorithm

Late October
Started 100s of client calls and onboarded over 50 coaches

Late October
Launched packages payments

Early November
Over 150 coach-client matches on platform

Early November
Launched a multi- touchpoint email engagement campaign

The following two pages are for industry analysis.


This slide includes information the cofounders collected during introductory calls with people in their network about coaching.


Then, there are two pages dedicated to Skye’s marketing practices.


The slide reads:

With a combination of events, influencers, and endorsements, we are generating a lot of buzz.


Science of Happiness
Productivity and Creativity Power of Support
Your Value System
From Founder to Leader
Mental and Emotional Fitness

Influencer Promotion
Devon Levesque – 501k
Summit – 56.7k
Minnie Kim – 74k
Val Chapman – 29.3k
Natalie Hill Jensen 15k
Erica Saeur – 14k
Quddus – 14k
Jenna Starkey – 1.5k
Dale Moss – 700k


Channel Partnerships
We have engaged in high level partnership discussions with some of the leading and most prestigious coaching institutions. We are also exploring partnerships with recruiting and law firms.

Social Marketing
Instagram and Linkedin have been strong organic channels that can be improved with targeted paid marketing efforts.


“Investors liked seeing this page,” Wolf said. “It showed how we started with organic events. Community’s a huge part of our work. We have about five in-person events a month. Coaches get to practice some new topic or programming, and our clients get to meet each other.”

The next page, edited for confidentiality, includes financial projections.


This slide details Skye’s financial projections through 2026, but it has been edited for confidentiality reasons.

The next page details the marketing and business development through Q3 2022.


The next page analyzes competitors.


Then, the deck gives some background about the cofounders.


And the company’s board of advisors.


The following 14 pages are part of an appendix.


This appendix was originally envisioned as a part for “traditional pitch deck needs,” like market size, competitors, and financial projections.

As Wolf realized that investors would ask questions about certain elements earlier on in the pitch — like competitors and projections — she moved them up the deck.


The first two pages in the appendix gives some background about the first days of Skye.



And what they learned about their potential clients and the challenges they face.


The next page includes a product-market fit analysis.


Then it moves into Skye’s business model.


In this deck, Skye projected to withhold a 5% fee from coaches, but that number has now increased to 10%.

And their target audience.


The following page highlights the untapped market potential.


Then it lists what services Skye offers coaches.


And what services it offers clients.


The next page lists Skye’s business partners, both on the coaching and client side.


And how it plans to be a combination of the business management tools coaches already use.


The next page, edited for confidentiality, includes business development and financial projections.


This slide has been edited for confidentiality reasons.

Towards the end, there is a page with screenshots highlighting interest from prospective clients and the success of one of Skye’s first events in October 2021.


The deck concludes with a thank you page.

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