Lift Your Legacy: Doing work you love and leading by example with Oracle Vice President Des Cahill…

Lift Your Legacy: Doing work you love and leading by example with Oracle Vice President Des Cahill and Rabbi Jacob Rupp

“When I see my team doing great work (and I get to see that a lot!), it means I’ve been successful as a leader in creating an environment for them to grow and achieve. That’s important and fulfilling, as it’s part of giving back and creating the next generation of leaders.”

Oracle Vice President Des Cahill is the Chief Marketing Officer for Oracle CX. An expert in B2B software and marketing, Cahill has spent most of his career in Silicon Valley, helping companies develop, refine and tell their stories.

Thank you so much for doing this with us! What is your “backstory”?

Thanks for having me. After college, I moved from New York to San Francisco for a job opportunity and soon afterwards I discovered Silicon Valley. I joined Apple during the personal computer revolution and had an amazing nine year ride. At Apple I worked on early internet stuff, including concert webcasts and running Soon after Apple I found myself at Netscape during the hyper growth of the consumer web. Then I jumped into the SaaS cloud world full force with a number of start-up CMO and CEO roles in the valley. I joined Oracle in 2016 to head up marketing for our customer experience business, Oracle CX Cloud. It’s an exciting time in the customer experience area as the economy has shifted to an era where experience trumps product and Oracle is uniquely able to help our customers succeed in what we call “the experience economy.”

Can you share the funniest or most interesting story that happened to you since you began leading your company?

My favorite story was when I was the CMO at a digital marketing company called Ensighten. I had recently joined the company and we had a big event coming up, Adobe Summit. The prior year we had booked a giant percentage of our annual revenue at the show, so it was important to get the show right. After months of planning, Adobe called us two weeks before the show and told us we were kicked out of the show as they had a competitive product. The booth was gone, our hotel rooms were cancelled, and we had no admission to the conference. So we took the returned sponsorship check from Adobe and rented a bunch of shuttle vans at Salt Lake City airport. We wrapped them in branded signage stating “Banned in Salt Lake City” and gave everyone coming to Adobe Summit free shuttle rides to their hotels. We got way more leads than the booth ever would have. And every shuttle rider, even Adobe employees, heard our story during the shuttle ride. We dominated the social media discussion during the event too. Not only was it a blast, it was cost-effective marketing.

What was your biggest challenge to date either personally or professionally and how did you overcome it?

I would have to go back very early in my career when I was working at a financial consulting firm that handled retirement plans for large companies. I had discovered that my firm had screwed up months and months of 401(k) accounts for thousands of employees for one of our clients. Already unhappy with my firm, I had to be the one to tell this client about the problem and walk him through the lengthy process to fix it. After numerous difficult and tense meetings and months of work, we fixed the problem. There was a silver lining though — that client became one of my strongest business relationships. And through this experience, I learned the value of being honest, direct, and accountable. I also learned that the strongest relationships are often built out of the most difficult situations.

What does leadership mean to you and how do you best inspire others to lead?

I aim to lead by example. I am not afraid to get my hands dirty, put in a lot of hours of work to meet deadlines and push our business processes and output to new levels. Communication is a critical area of leadership I strive to improve on. I’m lucky to have great colleagues and employees who remind me of the value of a quick email after a trip or an annual team get together. Providing common context across the team is super important. I’m fortunate to work with a lot of great leaders at Oracle and I’m always looking to learn new leadership ideas from all of them.

None of us are able to achieve success without some help along the way. Is there a particular person who you are grateful towards who helped get you to where you are? Can you share a story?

My parents. The sacrifices they made to make me who I am really humble me. They were Irish immigrants who came to the United States when they were very young, without much money, and no college education. They worked very hard to provide me and my siblings with a nice middle class upbringing. My father was a veteran and New York City policeman who never talked much about his job or his time serving in U.S. Army during the Korean War. But when I was older, my brother-in-law researched my father’s Army career and discovered that he had been in some of the fiercest battles of the Korean War. As a parent of three young adults myself, I appreciate all the effort and unconditional love my parents gave me — not to mention the college tuition payments!

Was it difficult to fit your life into your business/career and how did you do that?

I have always been pretty good about finding a balance between personal life and my career. There are always peak work times when everything else takes a back seat. But if I can’t get my personal time in, in a few days I’m going to be miserable to work with and I’m not going to be thinking as clearly. Whether it’s going for a run, eating a meal with my family, playing guitar or reading a book, I’m at my best when I am recharged. My best thinking and processing actually happens during the recharge process. It’s a constant juggling act allocating time across personal, family and work priorities. But I’d say a healthy life balance is a necessary precursor to a successful long-term business career.

Did you find that as your success grew it became more difficult to focus on the other areas of your life?

Yes and no. As I advanced in my career, the work demands on my time increased — more travel, more meetings, more employees, and more decisions. But I’ve also realized in the last few years that my work life and personal life have more commonality than not. A lot of my personal time in the last 15 years has been spent playing music and performing in bands. And a lot of my work in the last 15 years has been spent presenting at conferences, talking to influencers, creating content, and recording videos. I’ve realized that at the end of the day, I enjoy telling stories to lots of people. Sometimes the story is a song on a stage at a bar. Sometimes the story is about customer experience or digital transformation on a stage at a tech industry conference. It’s all storytelling in the end and I enjoy all of the different ways I get to craft and tell stories.

Can you share five pieces of advice to other leaders about how to achieve the best balance between work and personal life?

  1. Work in a career area that connects with who you are. That’s 90% of it right there.
  2. Never give up on your personal passion. If it’s playing music, painting, traveling or whatever — maintain it at any level you can. It makes you a more interesting and well-rounded person.
  3. Turn off work email, Slack, Twitter, Instagram, phone at 7pm, as many nights as you can, to leave time for the rest of your life.
  4. Just as technology lets you work from anywhere, it also lets you work at any time. So take a break mid-day for a hike. Pick up your guitar for 30 minutes. You can catch up on work later.
  5. Multi-task at the gym. Email on the elliptical. Listen to podcasts on the spin bike. And sometimes it’s important to forget about work and fire up Spotify for your workout too.

What gives you the greatest sense of accomplishment and pride?

There are two things that give me pride and tell me that I have succeeded in my job. The first is when I see an idea or message that I originated being repeated back to me in someone else’s presentation. I get a great feeling when someone has adopted my idea as their own and they are now sharing it. This is how I know that I have succeeded as a marketer. The second is when I see my team doing great work (and I get to see that a lot!). It means I’ve been successful as a leader in creating an environment for them to grow and achieve. That’s important and fulfilling, as it’s part of giving back and creating the next generation of leaders.

You are a person of great influence. If you could inspire a movement that would bring the most amount of good to the most amount of people, what would that be? You never know what your idea can trigger. 🙂

I would want to address the needs of homeless families. This is a big problem in the United States, especially in high cost areas like the San Francisco Bay Area. One of our favorite local charitable programs is LiveMoves /Haven Family House in Menlo Park, CA. They provide free temporary shelter for families in transition and do a great job of getting those families back into permanent housing and self-sufficiency.

What is the best way for people to connect with you on social media?

You can find me on twitter @descahill or on at Linkedin

About the author: Jacob Rupp is a coach, author, speaker, podcaster, and rabbi. He is the founder of Lift Your Legacy, a community that helps people live a more authentic life. He has a regular, syndicated column that appears in ThriveGlobal and Medium magazine. To learn more about him or to listen to the Lift Your Legacy podcast, search iTunes or visit his site:

Lift Your Legacy: Doing work you love and leading by example with Oracle Vice President Des Cahill… was originally published in Authority Magazine on Medium, where people are continuing the conversation by highlighting and responding to this story.