By Bob Johnston
January 24, 2022

Mark Hawkins – On Silicon Valley, Second Acts, and Startups

My first guest of the season is Mark Hawkins, a well-known figure in Silicon Valley and board member at Toast and Plaid.

Mark most recently served as CFO and President of Salesforce, before retiring to focus on Act 2. We spend a good chunk of time talking about Act 2s – it’s the start of a new year where many of us are re-visiting personal and professional goals and taking stock of our lives as we navigate the pandemic.

Mark was a guest speaker at an Executive Council webinar last year and, since then, I’ve been eager to have a more in-depth conversation with him as I  admire his career and personal ethos.

We start off our chat talking about Mark’s early education and him taking the atypical route (and associated risk) upon college graduation – passing up a high paying job at General Motors in his native Michigan to head out West and find a home in the technology industry. Despite landing a lower paying job in the Valley, this turned out to be a pivotal decision for Mark.

We also discuss Mark’s early role models, especially his Mother, and the importance of being open to mentorship throughout your career and paying it forward by mentoring others as you advance.

Mark and I then hit on the state of the technology industry and the startup world, covering fundraising and valuations…and the importance of keeping a ‘founder’s mindset’ as a company scales.

Finally, we pivot into Act 2 – what Mark is doing now at Alpha Elevation (hint: see above) from investing in startups, sitting on boards, and giving back through orgs such has Project Black. Plus, cranking out marathons!

Mark's Bio

Mark Hawkins is an award-winning executive who, for four decades, has led finance organizations at global software and technology companies including Salesforce, Dell, and Hewlett-Packard.

Raised in Michigan, Mark attended Michigan State where he studied operations management. His first job was at Hewlett-Packard, where at just 21, he was a buyer for the supply chain by day and getting his MBA in finance from University of Colorado Springs by night. Hewlett-Packard later sponsored him to attend the Advanced Management Program at Harvard Business School.

Mark was the President and CFO of Salesforce until 2021 and is currently a board member at Toast, Plaid, DataRobot, Secureworks, and sits on the NYSE Listed Company Advisory Board.

We stand on the shoulders of our family, our community, our educators, and our mentors.
On the importance of recognizing one's journey
When we look back 20 years from now, we’re going to realize this was just one inning of a nine inning game.
On where we are overall in the world of technology, despite the past 20 years of advancements


7:06 Tell us more about your education. Was silicon valley on your radar back in the 80s when you were in undergrad and graduate school?
Before attending Harvard Business School Mark went to Michigan State University. He went to a recruitment fair in 1981. General Motors made the highest paying offer, and given that Mark was from Michigan, it felt like the logical choice. However, his gut and experience told him that the technology industry burgeoning out West was the future, so he took a 10% pay cut and went to work for Hewlett Packard.

12:46 Back in 1981 was your decision to move from Michigan to chase a dream out West in the tech industry considered radical by your peers?
The decision to turn down offers from established companies like General Motors in order to go work at Hewlett Packard definitely turned heads. But Mark had studied the situation carefully, and was confident he was making the right choice. Plus he had the blessings of his mother, who always trusted his judgment.

14:41 What was your first job at HP?
Mark started in the manufacturing management side at HP. A buyer for the supply chain at 21, it was a great way for him to learn the company’s financial system from all angles.

15:57 Where’s your hometown?
Mark grew up in Milan, Michigan. Growing up in a largely agrarian community instilled a strong work ethic. Mark credits his mother for being his greatest mentor in terms of great advice.

18:10 What were some of the advice and mantras your mom had that had an impact on you?
It’s always about who you surround yourself with. Be around people who are productive and who will lift you up, and you lift them up. To this day, this has been Mark’s North Star when it comes to business decisions.

21:29: Is tech still a meritocracy? Can you still start a successful business out of your garage?
According to the 40-year tech veteran in the room, tech is only just getting started. Young startups are willing to risk it all to do something different. There are more sources than ever to fund different projects. Companies are staying private longer, which has certain implications. 

26:53 Some of the deals are head-scratchers these days. On the valuation front, it’s 10-15x from where we thought the valuations were pretty rich.

Valuations ebb and flow, but if you have enough innovation, that is the lead indicator of your ability to grow. When you think of digitalization and modernization, especially in light of the pandemic, there is immense opportunity.

29:06 When you vet a startup, having that foresight comes from years of experience and working alongside visionaries like Michael Dell and Marc Benioff.
Don’t be afraid to run into the fire when others are running away from the fire if you sense an opportunity.

32:19 Is it possible to still have a founder mindset permeate through a company that is growing and scaling so successfully?
Founders are critical in defining and setting the course for company culture. Good business leaders will figure out how to amplify their founder’s ethos and culture at every opportunity and with every stakeholder.

35:49 In terms of the next chapter in your life, what new projects or ventures are you feeling excited about?
Fueled by a desire to keep learning and make an impact, Mark created a career talk called Career Incorporated, how to see yourself as the CEO of you.
He has boards that he sits on, including those of Toast, DataRobot, and Secureworks and he created Alpha Elevation, which is a CEO advisory company. He’s involved with select NGOs, and is writing a book with his sons.

41:48 What is the book project with your sons?
It’s part of a long tradition, where, even when they were so young he had to hold their hands while they walked, Mark and his sons would take a walk after dinner. Mark always made dinner and the post-dinner walks a priority, even if it meant staying up until 2am to get his work done. The title of the book is ‘Walk With My Sons.’

45:56 Is there a common metric or trait that you see or implement so you can determine whether a founder/CEO is topnotch?
A lot of it comes down to assessment of leadership, and a big part of leadership is the ability to get things done through others. Another part of leadership is reliability and having a true vision and courage. How do you know if someone is a kind of person you would follow into battle?

49:07 Is the more purpose-driven type of culture that’s being developed at companies here to stay?
Trust is number one. And trust has to be earned every single day. You cannot be tonedeaf to your stakeholders.

55:25 What is a contrarian view that you hold that you are 100% convinced is true?
AI will create jobs. 

58:36 What’s on your browser?
The Wall Street Journal, The Economist, BBC, The World Economic Forum’s website. Mark is also a music lover who enjoys listening to classic rock and many other genres on Spotify.