If you asked me in May of 2018 if I thought my (selfie) recorded walk down the Fort Point boardwalk with Manjit Singh would lead to anything more than a one-time post, I would have told you no.
Turns out I was wrong.
Two years, ~18 miles walked, 17 cities, two continents and 99 episodes later, the #WeeklyWalk is celebrating its centennial! And to help mark the occasion, I wanted to share the 10 biggest things I’ve learned from these walks:
My arm gets really tired after five minutes of holding up my iPhone. I need to either work out more or keep the videos under five minutes.
When it comes to selling—especially to CXOs—most vendors don’t do their research. They try to sell to them without understanding their organization, their pain points or whether they’re even the right person to even be selling to. Know your target!
#TBT to my last pre-pandemic, non social distance #WeeklyWalk with Edna Conway, VP and GM Global Security, Risk and Compliance, Azure at Microsoft. Edna is a boss—and if you don’t know her, you should.
She let us in on her 2020 security theme, where she believes VCs should be investing their money, and what she’s cooking us for Sunday dinner (when this is all over).
Who else is really missing in person conversations?
Instead of a walk, I went for a virtual hike through the hills of Silicon Valley with Karl Mosgofian, CIO at Gainsight.
During our adventure, we talk about IT in a downturn and its cultural impact (two words: Zoom fatigue), how Gainsight is helping their customers now more than ever, and what internship you can hire Karl for should he ever decide IT isn’t his thing.
Welcome to In CASEYou Missed It, where I take a brief break from my Weekly Walks to get to know some of the most interesting and innovative personalities behind the greatest startups in the world.
Today I’m talking to Eric Muntz, CTO at Mailchimp, to find out what he believes are the most important qualities of a leader, his secret to achieving inbox zero, and the TV show he’s been on twice.
If there were a Mailchimp movie, or a movie about your life, who would play you?
That’s a tough one. I asked my wife, and she reminded me there’s an actor that she thinks I look like: Jesse Williams. He’s on Grey’s Anatomy. We’re both bi-racial and have really short hair—I think that’s where all the commonalities stop. But, hey, if I get to pick who’s playing me—yeah, I’d go with that.
Leandra Fishman, VP of Growth Sales at Twilio, sat down with me (literally) to talk about what hasn’t changed when it comes to Twilio’s end user strategy despite the pandemic—and the steps you should be taking to effectively scale your sales strategy and team.
Stick around until the end to find out where she’s most looking forward to going post-pandemic
Welcome to the very first edition of In Casey You Missed It, where I take a brief break from my Weekly Walks to get to know the some of the most interesting and innovative personalities behind the greatest startups in the world.
Today we’re talking to Calendly Founder and CEO Tope Awotona to find out the best book he’s read in the last six months, what he’d be doing if the internet didn’t exist, and which actor would play him in a Calendly movie.
How do you explain what you do to parents, friends and kids?
I say, “We make it easy for business professionals to meet.”
Who is your favorite superhero? And what would your superpower be?
Do you know the comic Tintin? It’s not a superhero movie, but he’s this really cool kid detective. So what would my superpower be? I’d just be an awesome detective. I
COVID-19 has thrown us all for a loop—in our personal lives and in our professional lives. As companies scramble to adjust to a dispersed workforce, internal communication and team management have rocketed to the top of the priority list.
Even companies that know how to manage remote teams are struggling to help employees maintain productivity while dealing with constant distractions and anxiety.
If you’re a leader, how can you help your team navigate these unusual times with grace and good humor?
Working through a crisis isn’t new territory for Carol Meyers, an inspiring leader and self-proclaimed growth junkie who has helped four companies—Shiva, Unica, LogMeIn and Rapid7—through successful IPOs. One of those happened during the Great Recession.
I reached out to Carol to get her thoughts on what people need most during times like these. Here’s what she had to say:
For this #WeeklyWalk, Bryan Wise, former salesman and current CIO at GitLab, and I took to the tracks at the oldest train station along the Caltrain in Menlo Park. Socially distanced, of course.
Bryan shares his thoughts on why IT at a product led org is a different mindset, and he spills GitLab’s remote work secrets. (Did you know they’re the world’s largest all-remote workforce?)
Those who went through the 2001 and 2008 economic downturns emerged with valuable lessons on navigating a crisis—not to mention a heck of a lot of resilience.
Currently President at SurveyMonkey, Tom Hale helped Macromedia survive and thrive after the dot-com bubble and had a ringside seat at Redpoint Ventures during the Great Recession of 2008.
Here, Tom shares practical advice on keeping your team calm, taking risks, and why it’s important right now for leaders to show vulnerability.
You were SVP of Business Strategy at Macromedia as the dot-com bubble burst and the economy halted after 9/11. Can you walk me through what that was like?
Tom: I was at Macromedia at the time, and we were right in the middle of the largest acquisition we’d ever done. We had a great business (400M/1500 employees) in web tools and multimedia, and we wanted to be in the app server
The Weekly Walks haven’t been the same without my sunglasses, so this week I took my (virtual) #WeeklyWalk outdoors to catch up with Anne DelSanto, former EVP and GM at Salesforce and current board member at Juniper Networks and Traction on Demand. We talk about why your customer is so important regardless of company size and type, the first steps to take on the independent board journey, and what her career would be in another life.