Today’s episode will be a bit different in that the focus of the discussion will be on leaders and leadership. Here to discuss this topic with me is Bottomline Technologies CEO, Rob Eberle. Rob has been CEO of Bottomline for almost 15 years now, and under his leadership the company has become a leading provider of business payment solutions delivered across multiple geographies and markets. The growth is reflected in the financial results as well. Since 2011, Bottomline has gone from $55M in subscription revenues to just under $300M in 2019, and from $42M in adjusted EBITDA (Earnings before interest, taxes, depreciation and amortization) to $100M during that same period. Thousands of corporations around the world rely on Bottomline for domestic and international payments, efficient cash management, automated workflows for payment processing and bill review, and state of the art fraud detection, behavioral analytics and regulatory compliance solutions. Some of the leadership topics I touch on with Rob include the importance of setting the right tone early on, the biggest challenges of being CEO, the connection between leadership and mentorship, and his thoughts on the most important qualities in a good leader.

Timestamps

00:01:38 Working yourself out of a task as a leader

00:04:57 Mentorship and role models

00:07:42 Leaders vs. managers

00:09:57 Complete alignment with employees, "did you knows" emails from employees

00:12:06 3 components of good decision making

00:15:00 Hardest thing a leader has to do, handling cutting an employee

00:20:40 The leader is responsible, setting the right tone early on

00:22:40 How often do you fail as a leader

00:24:47 Every company over time gets the people it deserves

00:27:19 We all have leadership experiences

00:30:42 Changes in leadership when moving up the chain of command

00:32:41 Hardest types of decisions he has to make at Bottomline

00:33:58 Challenges when leading a public company

00:37:15 Leadership heroes?

00:40:10 Most important qualities in a good leader

00:41:15 His advice to the next CEO of Bottomline

00:43:25 The day he was appointed CEO of Bottomline

00:45:50 What's kept him driven as a leader

00:47:13 Advice for a first time company team leader