Why I’m Writing About My Experience as a First-Time CEO

In September 2016, I left Salesforce after 9+ years to take on my first CEO role at Invoca. I was excited to take on the new challenge, but also somewhat intimidated by the unknowns of the position. I had lots of questions swirling in my head, from “how do the mechanics of a board meeting work?” to “how should I spend my first 30 days in the role?”

I believe in the value of “benchmarking” and getting peer perspectives about business problems. So, before taking the role at Invoca, I spent a lot of time talking to venture capitalists and former Salesforce colleagues about what to expect in a CEO role, what challenges I would likely face, and how best to prepare myself. In my time at Salesforce, I was fortunate to observe leaders who came into the Salesforce family via acquisition, like Scott Dorsey and Scott Mccorkle (ExactTarget), Marcel LeBrun (Radian6), michael lazerow (Buddy Media), alex bard(Assistly, and later Campaign Monitor), Adam Blitzer (Pardot), and Godard Abel (SteelBrick).

And since there is a great network of ex-Salesforce employees who have moved on to CEO / COO positions, I’ve also spoken with people like Brett Queener (SmartRecruiters), Chuck Ganapathi (Tact), Clara Shih (Hearsay), Tim Barker (Datasift), Doug Bewsher (Leadsift), Andy MacMillan (Act-On), Anshu Sharma (Learning Motors), and jager mcconnell(Crunchbase). Or I simply observed old colleagues and Salesforce alumni like Todd McKinnon (Okta), Tien Tzuo (Zuora), Kraig Swensrud(GetFeedback), Sean Whiteley (GetFeedback), Dave Kellogg (Host Analytics), and Elay Cohen (SalesHood).

I learned a lot from those conversations, and I doubled down by listening to SaaStr episodes while driving my kids to soccer games (thank you Jason M. Lemkin… my 10- and 8-year-olds now recognize Harry Stebbings’ voice!) Yet as I settled in for my first few months at Invoca, the tables began to turn; I started to get questions from peers and former colleagues about “how should I think about the path to becoming a CEO?” and “what’s surprised you most about the new job?”

Those questions pointed me toward sharing my thoughts and experiences online, where other people could benefit and discuss at a broader scale. I’m influenced by my experience working on Salesforce Chatter, an enterprise collaboration platform, where I saw firsthand the benefits of openly sharing information and lessons learned. And I’m inspired by one of our investors at Invoca, Mark Suster, who offers insights at Both Sides of the Table that I regularly shared with my colleagues at Salesforce. Finally, on a personal level, I’ve always loved writing, and using the written word to share ideas and drive engaging conversations.

After reflecting on these thoughts, the takeaway was clear — I wanted to write about my experience as a first-time CEO. The advice and suggestions I have received were invaluable, so I thought it would be useful to synthesize and share my observations for others in positions like mine. I also (selfishly) hoped it would lead to conversations that make me more effective in my job at Invoca.

My only concern was making sure Invoca “came first” and I didn’t inadvertently do or share something to hurt the company. So, in consultation with our management team, I settled on these ground rules for content to share:

• Nothing will be company confidential. Duh! But more importantly, I believe the value in sharing is really about the process of making decisions and driving execution, not the details of the end result.
• A minimum 3-month delay on publishing lessons learned. I want to do this for two reasons — foremost, to protect company interests, but also to ensure my thoughts and reflections have enough time to develop and crystallize before I share them in writing.
• Nothing personal. A no-brainer in general…. I expect some observations may entail anecdotes related to employees, but I won’t share anything that names an individual explicitly or by inference. If it’s questionable that someone might feel “called out,” I’ll always ask them to review a draft before publication.

I’ll be sharing several posts in the next week to get started, and then plan for a cadence of once or twice a month. I hope the content will lead to some interesting discussions, not only for the benefits of others, but also as I continue to learn and develop myself. And hopefully you will find value in some of the insights that my peers have been kind enough to share with me.

I look forward to the discussion, and feel free to let me know what topics you’re interested in or looking to explore.