Meet SaaStr’s Most Respected Leaders of 2019. Our most popular CEO, COO’s and Presidents that spoke at SaaStr Annual 2019. Curious how we came up with this list? We found our most popular speakers by speaker views and likes, session bookmarks and ratings weighing categories more heavily for overall rating than initial interest. Using magic (standard deviation) we came up with the best of the best of our sessions as voted by you, our SaaStr community.

Every week we’ll be rolling out new winners until we get to the very pinnacle of our list. Keep your eyes peeled as we unveil the list and a bit more about your favorite leaders.

SaaStr’s Most Respected Leader Awards Number: 9 to 5

Brian Halligan Hubspot Founder/CEO
About Brian…

Our metrics suggest that our attendees were very excited about Brian as a speaker. His high marks in our “speaker likes” metric lands him at number five on our list. Hubspot is an inbound marketing and sales software company based in Massachusetts.

Brian Halligan is co-founder and CEO of Hubpost. He co-founded the company with Dharmesh Shah, the two met while they were grad students at M.I.T. Prior to this, he was a Venture Partner at Longworth Ventures, VP of Sales at Groove Networks (acquired by Microsoft.)

His thoughts on leadership in a nutshell? “A leader has 3 responsibilities that are akin to a bus. First, the leader must have a clear set of directions in mind on where the bus is headed. Second, the leader must have the right people on the bus who are excited about the direction and work well together. Third, the leader must have enough gas (cash) in the tank to get to their destination.”


Michael Seibel Y Combinator Founder/CEO
About Michael…

Number six on our list, Y Combinator’s Michael Seibel who was popular across all metrics but saw especially high interest in his speaker profile and pre-registrations months before the event. Y Combinator is a seed accelerator. YC has funded over 1,900 startups since 2005 including Airbnb, coinbase, Dropbox, Stripe, Flexport, instacart and reddit.

Michael Seibel was co-founder and CEO of from 2007-2011 which eventually became Twitch. He then moved on to co-found Socialcam in 2012, participated in Y Combinator and eventually sold to Autodesk for $60M. Today he is a full-time partner and CEO of Y Combinator.

Karen Peacock Intercom COO

About Karen…

**Intercom contributed to the blurb below.

Karen is number seven on our list with high marks in all metrics. Her session has proven time and again to be one of our most popular amongst attendees, chock full of actionable advice for the SaaStr community. As she encourages in her talk, she wants attendees to “Fall in love with the problem, not the solution.” She also joined SaaStr’s podcast where she discussed growing Intercom from 350 to 600 people and here was her advice on two common scaling mistakes: “The first mistake is taking your eyes off the customer. Leaders who do so will lose their product market fit. The second mistake is not having the right amount of process. Not enough process and your team will get pulled in different directions. Too much process and people will get mired in meetings and documentation.”

Karen Peacock is Intercom’s Chief Operating Officer, where she has been since 2017. Prior to Intercom, she held leadership positions at Intuit for 14 years, most recently as the SVP of Small Business responsible for all of Intuit’s products and services for small business including QuickBooks accounting, payroll and payments, a $2.5B business. Karen has been an advisor to Namely and Thanx as well as a board member for Revel Systems.


Jay Simons Atlassian President
About Jay…

Jay Simons rises to number eight on our list with very high speaker views and bookmarks leading up to SaaStr Annual. His session focused on scaling an open culture. In fact, Atlassians were entrusted with the knowledge that the company was going public four months before it filed.

Jay Simons rose up the ranks from Area Sales Manager with Plumtree software to VP of Product Marketing and Strategy. From there he went on to BEA Systems as VP of Marketing. His tenure at Atlassian began in 2008 where he rose from VP of Sales and Marketing to President.

Andy Wilson Logikcull Founder/CEO
About Andy…

Andy Wilson ranks nine on our list ranked highest in the session average metric. This means that attendees had such a great experience in the session that they upvoted the content afterward.

Andy Wilson is CEO and Founder of Logikcull. Prior to Logickull Andy was a software developer at EDS (an HP Company). He has helmed Logikcull as CEO since its founding in 2004 as an e-discovery services company. The company pivoted to cloud-based software in 2013 and counts Chubb, the City of Chicago and Burr Forman among its customers.

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