From Cisco CEO to Serial Start-Up Founder with Doug Dennerline of Betterworks

In this episode, Ryan is joined by an individual with possibly the deepest and richest background of anyone he has ever interviewed! Doug Dennerline originally started out in Silicon Valley back in 1982 at HP, he then worked his way to becoming the CEO of Cisco and took it from 400 sales reps to 6000 with a 9.8 billion dollar budget. After this, Dough was the CEO of Webex before founding and selling his first start-up and now is onto his newest start-up called Betterworks which is reinventing the way people are managed.

Doug and Ryan focus on leadership and people management in this episode including the importance of finding the right HR partner, how to build a great team and incentivise them to generate revenue and how AI will change the HR world forever.


  • BetterWorks is trying to reinvent the processes in how large companies manage people.
  • 70% of large companies still do annual reviews even though most people hate it and it doesn’t improve performance. What’s more important is creating conversations between managers and employees and becoming aligned with goals and targets.
  • Doug joined Cisco in 1998, during the dotcom boom which he says is still one of the greatest experiences of his life, being there when so much was happening.
  • Doug’s tech guy went on to be the CEO and founder of Zoom!
  • Many more businesses are recognising that their people are their most important asset, Doug gets great satisfaction from seeing CEOs and HR professionals who love the Betterworks product, he gets to see its impact on the workplace.
  • Companies that value their people, whose employees feel they have purpose and direction in the company create more revenue.
  • CEOs should spend time with their people who have to go through their review processes, this will make them realise things need to change.
  • AI will change the world of HR, from helping with how to have difficult conversations to writing reviews.


“The annual performance review, research has proven people hate giving it, people hate getting it and it doesn’t improve performance”

“The hardest people worked for me was when I was able to connect the corporate goals to individual goals, both personally and professionally”

“Cisco just had massive growth when I was there”

“We bought Webex in 8 days, closed that deal in 8 days!”

“I went from being a sales leader to an operator, a CEO, and I’ve been running SaaS companies ever since”

“I really enjoyed the start-up aspect, the impact you can have on a smaller company”

“The company with the best team has the highest chance of winning”

“I have a very low ego environment in my company and I don’t believe in lines”

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Ryan Staley

Founder and CEO

Whale Boss




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