Grit23 Tammi 2023

#122 President & Board Member at Freshworks, Dennis Woodside: What If This Goes Really Well?

Freshworks president Dennis Woodside copes with stress by running as often as he can, a habit that began when he was CEO of Motorola Mobility. So far, he has run “16 to 17” Ironman triathlons. He’s also continually challenging himself in his professional life, leaving Motorola in 2014 to advise the founder-CEOs: Dropbox’s Drew Houston, Impossible Foods’ Pat Brown, and now Freshworks’ Girish Mathrubootham. Dennis’ advice for anyone working with founders is to “have empathy” for what they’re going through, and to understand what motivates them. Without that understanding, he says, you won’t be able to arrive at a shared vision for the company.

In this episode, Dennis and Joubin discuss mega-acquisitions, the smartphone paradigm shift, triathlons and competitiveness, winning every category, “softening up,” global cities, Google interview questions, spreading Silicon Valley culture, the “chrome panda moment,” hiring the right people, “Where do you want to be in five years?”, evaluating new opportunities, and building trust with founders.

In this episode, we cover:

Google’s acquisition of Motorola and how Dennis went from ad exec to first-time CEO (02:00)
Did Dennis like being the CEO of Motorola? (08:04)
The stress of the new job and dealing with it through exercise (13:02)
Dennis’ impressive résumé and what dinner conversation was like growing up (18:37)
Going to Korea and choosing the harder path (23:00)
Joining Google in 2003 as a general problem-solver (26:23)
Hiring “scouts” all around the world to better understand the internet (30:41)
Leaving Motorola to mentor Dropbox CEO Drew Houston (39:12)
Checking your ego and the listening tour that wasn’t (42:20)
Dropbox’s IPO and why the stock has been relatively flat (48:38)
Changing jobs without breaks, and spotting new opportunities like Freshworks (52:19)
Tips for working with founders and interrogating the status quo (58:02)
Dennis’ most unique OKR at Dropbox (01:02:39)

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