We launched sky with a community first approach.

We partnered with so House and Forbes and there was a fragmented, decentralized coaching market.

We're approached by a few really compelling leaders in the space across hr, tech and coaching itself and sounding for particularly, we really aligned with our mission to ensure that everyone had access to a coach that was right for them and one singular, easy to use platform.

Being transparent.

Along the whole way, we created a lot of trust and kept the team with us through it.

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Welcome back to Lead the Team with number one bestselling author and in demand corporate trainer Ben Fanning.

On this podcast, the world's most innovative senior leaders share their top success strategies to motivate your direct reports, cultivate your top leaders and accelerate your career.

Let's get started.

Here's Ben.

All right everybody, welcome back to lead the team.

Today I have for you Jess Wolf who is the co founder of sky, the executive coaching platform backed by venture capitalist firms including Stellation, Greylock, Insight and bam.

And she's actually also the recently exited CEO.

So she's got a fascinating journey and some big things that have happened recently.

She's going to share all this with us today.

And sky has exited to the sounding board.

Go check them out.

Jessica's got an incredible background.

Formerly head of the Forbes under 30 list and she ran community for Iconics.

Jess, welcome to lead the team.

Thank you.

So happy to be here and excited to be in this conversation.

So when you exit a company as CEO, what's the first thing you do?

The big question and one I'm getting a lot.

I think the advice I've gotten is to take a break.

People say you're almost like a soon to be emerging butterfly and so you have to go into the cocoon and reflect and think about what you really loved on your entrepreneurial journey and what you change and lean into.

I think your network understanding what other people are working on and what's exciting in their industries to potentially find the next spark for yourself.

So I think a little bit like staring into the abyss right now, but eager to, I think, just jump outside of what I've been doing every day.

When you're building a company, you're so narrowly focused, you forget about all the things that are happening in the world beyond you.

Yeah.

There's probably like a crescendo of stress leading up.

Like we're trying to do all this.

It's so focused.

Like you say, we're kind of just so focused on that and then you can get to take a breath.

And I love the fact that y'all.

Did y'all notice she's asking herself very coaching related self reflection questions, which I am assuming has been ingrained in you throughout the years.

And I want to get into the M A, but I'm curious.

Yeah.

You know, you're relying on those coaching questions now.

Why get into coaching?

Why build sky in the first place?

Sure.

So my background's been in community development across a variety of industries, from hospitality to events to media to real estate.

And your role as a community builder, of course, is to support the marketing and events and sales related functions.

But at the heart of it is to ensure that people within your community are finding the most value possible and attaching that to your brand.

And I found that, you know, that's a very human, human role.

And so I was often speaking with community members and the things that they wanted at the end of the day were particularly around connection and feeling seen.

There's many ways that you can fulfill that.

Ultimately, community itself is about connection.

So you're offering that there.

But as I dove deeper, I realized, you know, the support that a lot of people were looking for existed a little bit within the therapeutic space, but I thought could be even stronger within the coaching arena.

And so launched a coaching platform, really to answer the calls I heard throughout my journey as a community builder.

And we launched sky with a community first approach.

And what I mean by that is our go to market strategy was entirely community driven.

And so we started out as a consumer platform supporting individuals and sort of their professional goals.

And what we did is we partnered with so House and Forbes to host live events featuring coaches who spoke on their expertise.

And this allowed people to get a taste of what coaching could be like for them and build, of course, you know, friendships and relationships, ultimately community.

And so, yeah, so really interesting, y'all.

So it's not like, hey, you know, Jess was a coach.

It's like, hey, I want to bring coaching to what it was.

Hey, I was serving communities and we saw this need and instead of Offering where my mind would be like, oh, well, so and so needs a coach, know, I'll, I'll step into that arena.

You're like, you know, let's build a, let's build these events and let's build a platform.

So that's the way your mind went.

Right.

Versus the opposite.

I think a lot of people say, hey, we're gonna start a coaching company.

But that's not where sky started.

Yeah, I think the market was also right for disruption.

There's fragmented, decentralized coaching market.

Not a lot of elements of trust.

The tooling was disparate.

And I think for coaches and as well as the other side of the market for leadership and HR buyers and leaders, a lot of options, but not necessarily the right options.

And so we had an opportunity to come in with something new and differentiated.

Yeah.

Because the problem is, and I've, I'm ICF certified coach, I've been in that world for a while is, you know, you have executives who need coaches and, but they don't know where to start.

And maybe they have, they have their chro say, hey, I need some coaches.

And they're like, well, I work with so and so at this company or I saw this person's book or like I say it's very fragmented.

It's like a one on one negotiation with these coaches at these executive levels.

Absolutely.

Which makes it really hard for scale.

And so sky and Sounding Board's mission really was to ensure that everyone had access to a coach that was right for them and that the leaders of said organization had the ability to scale that coaching over time and in one singular, easy to use platform.

And working with Forbes on the.

Was it under 30 list?

Yes.

What is that like?

So the, this is like the superhuman list of people under 30 that are changing the world.

Is that, that's the list, right?

Yeah, it's.

How does one put this together?

You know, so I was on the community side and my good friend was running sort of the selection process of the list.

But my role is once, once you made the list prior to me coming on board, there wasn't a lot of opportunity for connection unless you decided you wanted to find the people on the list and reach out to them on LinkedIn.

And Forbes saw an opportunity to really, you know, leverage these, these leaders for a broader community that would of course, you know, best serve them in their business interests, but also support the Forbes brand and ecosystem.

And so we built a worldwide community with boards in all major cities, host about two events a month and tie into our or there now larger summits.

So it's a, it's a very tight knit community that's still running today.

I love jumping in and out and going to the events in San Francisco and New York.

My role was launching that and setting up the structure to ensure that could sustain.

So when did you realize in life or maybe the defining moment or a time when you realize I've got a knack for this.

Like were you the kid back in kindergarten who was like always having the parties at their house or getting people.

Together or, you know, I wasn't.

My first role I think really exposed me to the power of community.

I was running the first of its kind, ultra luxury co working space and I was their first membership or sales leader.

And ultra luxury, yes, it's beautiful in terms of luxury, I should say more creative in terms of design and the food that was served.

And I think it was very fashion forward.

And so that was kind of unique at the time to have an office that focused so much on the beauty and aesthetics of the space as a means of inspiring your work every day.

And they too were very community driven in the sense that they really fostered a connection among the members and encouraged people to meet and become friends and do business together.

But when I joined I, I was 22, didn't have a lot of experience and was selling, you know, desks and offices at this space that were maybe four times the amount that was on the market and nearby.

And so I quickly recognized that, you know, in order to complete these transactions and sales, not to make this too transactional, but I recognize that, you know, I had to be selling a lot more than just a desk and a chair, but the promise of the opportunity to meet people that might impact their world in some professional or personal way.

And so sort of leveraging that and leaning on that, I did end up the community that I think I'm happy to see.

There's been marriages that have come out of it and a lot of business partnerships.

And I'm still friends with many of the members that were there in the early days.

But we, we quickly filled the entire house and became kind of a wait listed membership.

And so from there I quickly recognized, you know, community isn't just a soft, fun, fuzzy thing to do, but really it can affect your bottom line dependent on kind of how you're driving community to support revenue.

Yes, people want to do business with people they know like and trust.

That's that old saying.

And clearly if you're building a community and it is more Expensive.

And you're saying, hey, yes, it's more expensive here, but we're.

Or not.

But we are.

And we are creating a community of people and there's value in that.

The people that are see the value are more likely to join and they're more likely to invest in the community because that's why they're there.

Exactly.

Self fulfilling, awesome experience.

I can see that.

Definitely.

Definitely.

Yeah.

Wow.

And, and, oh, wow, that's cool.

So fast forward to today.

So you go through this and you, you see the opportunity, you start this.

You know, watch us through.

You started sky, when you started sky, were you thinking, hey, I want to build, like I see this opportunity, I want to build this business in a way that it will be attractive to outside, outside investors, other companies.

Or did you start it as more of a, hey, I want to create this business because I see the need and then eventually you kind of work towards that, that sales approach.

Yeah, great question.

So, you know, I created the business because I saw a gap, I saw an opportunity and I thought we had the tools and ability to fix it.

I saw an expand market in the coaching space.

I saw a lack of tools and like I said, a lack of centralization.

Particularly what we saw was the coaching platforms that existed were either really mass or on the flip side of the spectrum boutique and extraordinarily expensive.

And more importantly, I found that the coaches that existed on said platforms lacked industry and functional expertise.

And so what we did that was unique was ensure that a product leader was working with, you know, a former head of product from Pinterest or, you know, an engineer was working with the former director of engineering at Airbnb and be.

And so that context, what we called coaching with context, I thought was really relevant and important to a coaching engagement, which I think goes against a little bit of kind of the traditional ICF coaching model, which is, you know, more akin to powerful questioning and active listening rather than coaching slash strategic advisory.

So that's kind of where we differ and how we started to win some pretty big Fortune 500 in public companies.

But you know, when I, when I set out on this journey, that's kind of what, where I was.

But there's about three paths a founder could take, especially once they take on venture dollars.

And we raised and you know, you raise with the expectation that you can build the next billion dollar company.

And I think you go in, in there with a thesis of how you can do so, and then I think reality or the market or whatever it is can either accelerate you towards that or you can see, hey, there's, there's things that might not allow us to be that ginormous company.

And so what are the paths ahead of us?

So of course that one is becoming that billion dollar plus company and going public too is leaning into an acquisition and finding the right strategic or financial acquirer.

And then the last I think is probably turning to, I hate, I hate this word because I think it's the wrong word but more like a lifestyle or frankly a cash flowing business that could sustain over time.

The fourth option I don't like to talk about because that's a shutdown and no one likes to see that.

But of course that, that happens.

So three are typically like the most viable paths that you'd look out for.

But no, I don't think we set out to build a business that could be acquired.

I think we set out to build a business that we could continue to grow over time.

And we had some excellent models in the space who were a little bit different than us but had taken on that venture scale.

But we, you know, decided to go the M and A route because we were approached by a few really compelling leaders in the space across hr, tech and coaching itself.

And Sounding board particularly was really aligned with our mission.

And I recognize that Sounding Board could take our original, you know, dream for impact with much further.

I think having had more money, more people behind them and more resources than sky did as an early stage startup.

It sounds like sounding more from what I'm under, just my research, they're heavy on the technology side.

Right.

And you, and you all were heavier on the like coaching, higher level coaches, higher level relationships and companies.

Am I correct on that?

You guys kind of had the coaching.

Well maybe you explain it because they're not the same company.

Right.

You have different strengths.

Yeah, look, I think we were, I would like to think we were both, we leaned pretty heavily into our technology as well.

And so whole point was that we'd match you with a coach that was right for you, but our technology would manage the process over time to ensure like seamless interactions with your coach.

More importantly, data driven insights.

So you could actually tell like hey, is this coaching working?

What's actually like.

Yeah, which by the way is another huge gap in coaching.

Yes, it can feel good and you leave, but it's like, well what have I been doing the last couple months?

Right.

So I think technology and particularly with the admin of AI, there's going to be more and more ways to measure your growth.

But I would say Sounding board is very advanced on the technological front and has put a lot of, a lot of thought and effort into building a platform that I think is far beyond what sky has done on the technological front in terms of data and insights and serving customers with, you know, personalized journeys.

So, yes, I think our customers will find a lot in the, in the partnership.

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I'm really curious on your approach with the employees, you know, with the team that you built.

Right.

Because you built this company from the bottom up and people probably been with you the longest time.

And when, when the news came out, like, hey y'all, yeah, Wired, I'm curious, like, what happened?

What did they.

Did they know my.

I didn't experience.

When I was in my younger, in my career, I was working for a very large sporting goods company and we found out that we'd been acquired.

But it was just like all the, all the executives got VPs, got called into a meeting one day.

I was not one of them.

And I'll they came out and they were like high fiving and all this stuff and I'm like, we're like, what happened?

And they're like, well.

And I felt, I'm sure some leaders handled it very well, but I had no idea what was happening.

I felt completely in the dark and it really messed with my sense of loyalty to the company after that because of the way.

And a part of it was me too because I just didn't get what was happening.

I had got.

I'd been to business school, but I didn't understand the real business.

You know, you only learn so much business school.

Yeah, of course.

So what was your approach?

Was a story, you know, how did you.

Well, what were the emotions of it and all that fun stuff.

Yeah, I actually think that was one of the hardest parts of the process was ensuring that I was keeping my team motivated and focused, but at the same time ensuring there was a sense of transparency.

I didn't want them to feel like we had hidden this from them.

Of course, it sounds like you are a much larger company.

You know, we were anywhere from seven to 14 people over our sky journey.

And that's, that's a small team and much easier to manage.

Yeah, because the coaches were basically contractors.

Right.

All of your, your coaching network, they were independent, they weren't hired coaches.

Yeah, exactly.

1099.

So we had to be thoughtful around our communications to our coaches and customers particularly as well.

But with the team, I think what we did is early on, I let them know that this.

I always kind of reiterated, you know, the outcomes for a startup.

And when, when they interviewed with us, I said, you know, there's, there's three potential outcomes for us and I'm going to pursue the one that I feel like is most lucrative and meaningful, impactful for our team.

And I hope you'll rely on me and trust in me as CEO to steer the ship in the right direction.

And so we had a strategy meeting every month and in that strategy meeting and give a very transparent update around.

Here's our Runway.

From a cash perspective, this is where we're leaning in terms of strategy.

This is what we have to do from a revenue point.

And so everyone was on the same page.

I think it was still hard in the end.

I think people still felt, oh my gosh, this major chapter in our lives is over.

And so it was bittersweet.

But I think being transparent along the whole way while risky because there was the risk of flight from some team members, which would have really hurt our business in the process.

I think overall created a lot of trust and kept the team with us through it.

So it was helpful.

Yeah, great.

Some great examples there.

One is not hiding it and being as transparent as you can and being upfront with them on, hey, this is.

You don't, you don't have to always say, hey, we're going to be acquired and this was going to happen.

But I like how you presented different scenarios to people and I think that's always, hey, this is possible, this is possible, this is possible.

And allow them to be on that journey.

And also I think that one of these that gets missed and I look back over that time period for me is no one said, ben, you need to be learning what this is like going through this experience.

This is like the best business school, advanced business school thing you can go through.

And then years later, I ended up working for Honeywell for over a decade where we made a lot of acquisitions as a company.

On the flip side, I wish I'd paid more attention to being the acquired company and.

But I didn't know how it felt.

And so when I was on that acquisition team, I often thought about, you know, what they were expecting, experiencing, you know, through that.

That's, that's good.

I think having a lot of empathy on the acquisition team, even though it is like an ex major milestone, but just recognizing that there's a lot of emotions and leaving behind a company you've built, I think is.

It's probably helps create a lot of trust between the acquirer and the team getting acquired.

Because the value of the company is not just your corporate contracts and your brand, your technology, it's the people.

Sure, yeah, that I've been there.

You know what, and this is a little bit divergent topic, but I'm really curious because you have a smaller team, they're remote, right?

A lot more remote.

Yeah.

Your customer, your clients are being coached remotely and your coaches are remote.

So you, and frankly, you live remote.

You live in different, you know, different places, right?

Coast to coast, you live New York, San Francisco.

How you.

You must be a ninja at managing our being a remote executive, leading a remote team, working with remote contractors and clients.

What's the, what's the secret saucer?

I think it all started with our core sky team and ensuring that there was a lot of trust built, which is ultimately done through really thoughtful communication.

We had a lot of structures in place to ensure that we were all aligned on what was happening with the business.

I'd say the one that was probably most important for us was our daily standup.

So every morning at 11am ET for 30 minutes, the team would come together and would walk through our essentially standup tracker.

And every leader had to input what they were going to accomplish that day.

And these were small, two large things with timelines, dates and a section like if you needed help, who you'd be asking help with, and then notes if something was delayed.

And we went through this every morning and I think people who are joining, you know, were nervous about this and thought this would be tedious and exhausting.

But we started with an icebreaker every morning so there was an element of connection.

And then we got into the details and this really helped me as an executive understand what every single person on my team was working on on a daily basis.

You know, what was getting kind of dropped and why, what people were prioritizing where I make adjustments into workload.

And then I could also take a temperature check on my culturally, how everyone was feeling emotionally as well.

And so this process of a daily standup really helped me ensure that I was being the most impactful leader I could be.

And then I Think, like I mentioned, we had our strategy meeting, we'd have our finance meeting, our weekly forecast meeting.

We had, we had meetings in place that were at the same time every week, sure that everyone prepared, that we were staying on top of what was necessary.

And then when we think about our broader community, we really did the same with both our coaches and customers.

Our coaches, you know, had Monday, every Monday office hours where they could drop in, ask questions about product, about the business, you know, had a extensive support library and team that they could turn to.

And then we built community for them as well.

So there was events and pods and a book club that they could be a part of.

And all these were ultimately avenues for connection, but really ways for us to ensure that we were in connection with our coaches and that they could turn to us when they needed us and that we could understand kind of how coaches were feeling about sky and feeling about their coaching engagements.

And lastly with our customers.

You know, a big part of our offering was, you know, insights and so in order to, you know, support in giving the most thoughtful insights on whether coaching was working for their teams or not, you know, we were in constant connection.

So we were providing data and having calls and we had a structure for how we engaged with HR team so that they felt really taken care of.

And then they also felt like they could come back to us with feedback at any time.

And I think being very present with your clients is critical.

And so we also made a lot of in person trips.

And this is all to say that, you know, in person often trumps everything.

And so we visited our clients a lot and our community for our people leaders was really robust.

We'd host about two dinners a month in our major cities.

And so there was always the opportunity for us as a team to connect with, you know, fellow coaches and clients in person.

So, most memorable community event or dinner that you had.

What, what was it and what made it so memorable?

Yeah, you know, I often think that the more intimate dinners are sometimes special, but we did have a full day long thought leadership conference, which really made me really proud.

We had about 10 different conversations with the president of Myers Briggs, our lead investor editor at Fortune, and a mix of leadership development experts and people who are just change makers in their industry.

And I think that the summit was directed all around professional development, which of course is what we stand for at Sky.

And so it was just an opportunity to really present, I think, all the learnings that we've had and all the relationships that we've built over the era and time at sky and we had about 200 plus people attend for the full day.

And it was.

It was really special.

It was great to see so many people in person and I feel like I learned so much.

So it was, I think, you know, a day we're really proud of.

Sounds like an amazing event.

Yeah.

I read about Myers Briggs being so connected to sky and the company.

I'm an estj.

My daughter has.

Is the opposite of everything I am.

And I think my wife is also in terms of the.

So we have some interesting dialogue.

Yeah, they're.

That they put up with me.

I'm a huge fan of Myers Briggs.

Yeah.

Exciting announcement there with my involvement with the team in the.

I'll.

I'll save it.

I'm happy to say it.

I'm happy to say it now, but in the case that it's not released, we might have to wait.

But I'm joining Myers Briggs board, which I'm thrilled about.

Congratulations.

Yeah, we're big fans of it.

Good.

I'm glad to hear it.

Yeah, my daughter did it.

Took it it in her as an eighth grader for the first time just recently.

So powerful.

And.

Yeah.

So I'm estj.

She's I n F.

I don't know.

I got whatever.

The opposite of infj.

Yeah.

Yeah.

And it's interesting.

It's interesting.

And it really illuminated a lot for me about her and my wife and I used to kind of.

Was she an introvert or she an extrovert?

It wasn't.

I.

I know they can kind of happen on a spectrum in terms of, you know, you're extremely extroverted or extremely introverted or somewhere in between.

But anyway, we've really enjoyed that.

Those conversations.

So anyway, something for listeners to think about.

Definitely.

I think it helps you interact with your team members more effectively when you have a baseline understanding of where they're coming from and then what environments and what.

What types of communication.

I land best with them.

So, yeah, it's a powerful tool.

Got a couple of quick fire questions, please.

All right.

What makes a great intimate dinner from a community building standpoint?

You've done probably hundreds of these things.

Yeah.

What's.

What are.

What makes it good?

One of my favorite books on this is the Art of Gathering by Prieta Parker.

And what I think she does so well is she.

It essentially says that, you know, every gathering needs a very detailed framework.

I think often we think, you know, it's good people, it's good food, it's good music.

We'll bring everyone together and everyone will have a good time.

And often that's the case.

But I think to create a lot of intention behind a gathering can ensure people, you know, know why they're there and also can feel and leave feeling like, you know, they learned something or met someone or just felt a sense of really purposeful joy in that gathering.

And so I believe in structure for a dinner gathering.

I always ha.

I start with, you know, introductions of some kind, as cheesy as it might sound.

But I think I.

I think I make it sound.

I think I make it tasteful at the dinner, you know, some form of a get to know you question.

My husband has leaned into this, although I think he was embarrassed by it at first when we first hosted, but he now does a game at most of our dinners called long Short.

So you share something you're long on, something you're shorting.

It can be, you know, political or it can be cultural.

And this really can stoke a lot of arguments.

But I think that really helps you get beyond just that surface conversation, which ultimately I think is what creates, you know, deeper relationships.

They're sharing it to all the people or they're sharing it to one.

Okay.

You know, in group conversation.

And typically how many people would be at an intimate level of gathering?

We typically at our dinners, like to host anywhere from like 8 to 12.

8 to 12.

That's a good number.

Yeah, I think that's a really good number.

But I think it's also important to have a mix of that, like one on one conversation with your neighbor and then also ensuring that there are some group conversations.

You can bring the group together because you were intentional in who you invited in the first place.

You want to ensure all the minds can share and get to know each other and then, as Priya Parker always says, having some ultimate conclusion to the evening too.

So I highly recommend the book.

It's helpful.

Okay, very good.

Next quick fire question.

What is your favorite coaching question?

Wow, that's a hard one.

It's my favorite coaching question.

One of your favorite, I should say, I'm sure there.

I don't know if I have like a question in particular, but something my coach always does that I really appreciate is she asks me when I'm sharing a statement or a feeling.

She asked me is what you're saying, a, I should do that or is it a I must do that?

And so helping me differentiate between what, like, I feel like I, I should do for others or, you know, society is impacting that decision versus what I really want to Do.

And so detangling kind of the motives behind my actions.

Really powerful.

Yeah, I love that.

And sometimes that can reveal so much about your to do list.

Yes, these are my shoulds, but maybe they're kids.

Right.

And there's not really.

I'm sure there's probably a lot of that when you're going through exiting too to figure out what you need to be doing.

Then with like a never ending to do list.

Yeah, yeah.

You mentioned those daily standup meetings and you'd often start them off with a icebreaker.

What was your default?

Or you're like your go to icebreaker.

Well, I had to get really creative because we have many days, every day had to not do the same icebreaker every day.

But one I really love and I do often is your six word story.

So you take two minutes when you think about the six words that define your life.

Some people get really creative and do mostly a poem.

Others just choose words that, you know, stand for different chapters in their life.

And then you don't explain it why, you just share those six words with the group.

And I think, you know, often you're like, oh yeah, I totally get those words for you.

And other times you're like, oh, wow, that surprises me.

And that's something that you can discuss and build a, you know, connection on later with your coworker or friend.

But I really like that practice.

So you give us some really cool ones that could work in a.

I'm sure for like a dinner, like an elegant dinner.

Like six words could be a sentence.

It could be just random words.

And the long, short game is long being I'm.

This is what I'm into.

I'm really all in on.

And short meaning.

I'm selling it.

Like this idea.

Exactly.

I'm moving out of that.

Sure.

Like you could say I'm long the wellness movement.

I'm short remote work.

Yeah.

Love it, love it.

So good.

Man.

Jess, this has been so much fun today and it's just so cool to get the behind the scenes from someone who just exited their company and what that was like, how you built it, where the idea of the company came from and then what you're heading into now and behind the scenes on your operating system when you're working there and how you're building that out.

Really, really cool.

But with all that in mind, what's your parting thought for our listeners today?

Parting thought, any way you want to take it.

It could be six words.

My six words, my parting thought is there's never the right time or a good time to pursue what you're hoping to pursue.

I think you can save money and go back to business school and delay having children or whatever it is that you're putting off in your life to, to pursue something.

But I think there's never, there's never going to be the precise right moment.

So just from my own experience, I think, I think go for it.

If you're hoping to pursue something and you're, and you've had it like in the back of your head and you're very excited about it, don't wait for this perfect moment in time because it doesn't exist.

Love it.

Thanks for that.

Thanks for coming on the show today, Jess.

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