What a difference a year makes.

2015 was a time of incredible growth for Skilljar. At this time last year, we’d just made the tough decision to pivot away from individuals/SMBs and focus on enterprises. We had early indicators that the market was promising but did not know whether this new direction would succeed. We still had capital from our angel raise, but were not on track to reach VC-expected milestones.

So I’m incredibly proud and gratified with the progress we’ve made in 2015. We went from virtually zero to dozens of enterprise customers post-pivot, continually learning from our customers along the path to achieving product-market fit and healthy revenue. We welcomed outstanding new team members, including raising a VC round from fantastic investors. Our product is truly enterprise-ready, including integrations with Marketo and Salesforce, SSO, and REST APIs – and we’re even closing new deals on New Year’s Eve.


As a founder who went through the early months of painful pivots, it’s wonderful to finally talk to customers who practically cry with joy on the phone when they find us, and an even better feeling once they’re live and achieving amazing business gains from Skilljar.

Which isn’t to say that it’s been all fun and games. We entered the year with high uncertainty and also knowing that 2015 would decide our fate one way or another. Early in the year, we won a game-changing deal with a Fortune 50 company, beating a wide field of competitors head-to-head, only to have it fall apart in procurement due to cancelling the project. For a small startup, these early, large deals can make or break your company, and it was heartbreaking to see this one disappear at such a critical juncture. 

As a CEO/co-founder, I also dealt with my own inner demons leading the team through a pivot, and later facing dozens upon dozens of fundraising rejections while paradoxically handling a strong pipeline of inbound sales requests. Processing the emotional journey has been challenging and a story that’s deserving of its own blog post one day.

Thinking through what made 2015 possible:

  • Innovative customers who provide us with lots of product feedback to help make it better. None of us have a training background, so Skilljar is truly a product and market opportunity that emerged from listening to our customers.
  • An incredible team including my co-founder Jason Stewart. I’m so grateful to be working with such a highly capable and motivated group of people. (Want to join the team? We’re hiring!)
  • Supportive angel investors that believed in our team and our vision, even when we were clawing for our first deal.
Going into 2016, l am more confident (and having more fun) than ever before. Thank you to our customers, employees, and investors for being part of our journey – can’t wait to see what 2016 brings!