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Best Practice: Jessica Wolf

In this new series, we invite business professionals and executives to The Malin for a conversation about what they do best and how others might follow their lead. This month, startup founder Jessica Wolf visits us on the heels of the official launch of Skye, her new career coaching platform.

With a resume that includes Neuehouse, Summit Series, and running the Forbes 30 Under 30 List, Jessica Wolf has spent much of her career in what she describes as "community building in the professional space." In keeping with that, her new startup Skye matches individuals with coaches in their industry and provides group coaching and management training. Here, she talks about a few things she took away from starting the business.

On starting simple. "When I first started, I believed I needed a technical co-founder because I wanted to create a scalable, venture bankable technology platform. I still believe that to be true. But something I was fighting against was this idea of the MVP—one says start with nothing and just see if it can be validated. I really wanted to only launch something that was perfect, so I struggled to MVP. If I had just created an MVP early to test the concept, I wouldn't have needed a CTO. Thankfully, when we tested it, it took off so partnering with my CTO ended up being a smart move. But for those looking to kickstart an idea, I think an MVP without anyone else could be a really good way to go."

On testing for demand. "I wanted to see if people wanted coaching, and I kind of believed they did but I wasn’t 100% certain. So we created these beautiful graphics and had all my friends post on their Instagram Stories, 'If you’re looking for a coach, sign up for a free consultation, and Jessica’s company will match you with a coach.' I had 30 of my friends post and we had 200 plus people book times on my calendar, so I was literally in 10 hours of meetings every day for weeks. I was like, Oh wow, okay, I guess I don't know if these people will actually purchase but there's something here."

On getting it right vs. getting it out. "We had built packages for coaches to sell that were based on individual sessions. And we quickly discovered that most coaches sell packages of months with two sessions. That's an extraordinarily difficult technical, logical thing to build. So we were about to launch and we didn't have a product that would be suitable for coaches, and our coaches didn't want to use the product. We needed to make the decision whether we launch something that's not totally right and hope that it takes off regardless, or do we fix it, delay, and do something that our customers want. We delayed and that was the right decision. It was a hard decision but it informed how we work now."

On remembering to take chances. "What I struggle with is, everyone says not to compare but you look at the market you're in—like I'm SAAS technology—and I'm constantly looking at the growth rates and the benchmark for the next raise. Just seeing what other founders are doing can feel like you're not measuring up. Funny enough, when I was 22 I didn't look at any of that, because ignorance is bliss. But I think it gave me a lot of competence and power just to break the mold and go for it and not really know what I was up against. Sometimes when I'm feeling these things, I try to reassume that mentality of, I'm just gonna try it, we're just gonna go for it and not be affected by the noise. That's my advice for others, too."

For more on Skye, visit joinskye.com.

Exclusive to Malin members: receive a complimentary discovery call with Jessica, a complimentary mini session with three recommended coaches, and $50 off your first month of coaching. Visit The Malin member app to redeem.

"I really wanted only to launch something that was perfect, so I really struggled to MVP. If I had just created an MVP early to test the concept, I wouldn't have needed a CTO. Thankfully, the test took off so partnering with my CTO ended up being a really smart move."

Best Practice: Jessica Wolf
Best Practice: Jessica Wolf

Interview and photography by The Malin Journal

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