View the illustration of Grad’s Journey

ZDNet called Grad Conn “a near perfect example of what a tech company CMO should be like.” He’s had lots of practice. Grad was at Microsoft for a dozen years where he served as CMO of the company’s $35B U.S. commercial business, in addition to holding other key roles at the company. He’s a serial entrepreneur on his fifth startup as either CEO or CMO. He started his career as a marketing executive at Procter & Gamble. Grad is now Chief Experience & Marketing Officer at Sprinklr

We asked him to share reflections from his career starting with three themes that have been present throughout his journey.


The three themes that have driven my career are people, process, and technology

What gives me the most career satisfaction is having an impact on the lives of the people I work with. I do a lot of 1:1 coaching. And I’m always looking for ways to help people grow. As I think about where I can invest in this with the most impact, I always look for ways that scale. I work hard to create a learning organization where every day people go home feeling like they learned something new. I do a lot of blogging. I have a daily podcast. At Microsoft I created a whole series of books, just for the team. The investment I make in content and the publishing is all non-commercial. I just do it so my team and my peers can use it. It’s about sharing what I know to help others grow. The great thrill in my life is when I haven’t talked to someone in years, sometimes decades, and they reach out to share that I had an impact on their life in some meaningful way. That’s all the gas I need to keep going every day.

The second theme is process. This one is a bit counter-intuitive because process is not naturally one of my core strengths. This is a lesson I learned the hard way in one of my own companies. It’s always good to learn on your own dime.  I am a very people-focused, content-focused person. Process is vital and the right level of process is the hygiene that keeps an organization healthy. I have built a nice group of people who are great at driving process, and I tend to overinvest in creating centralized services, desking, and process flow to help teams run more efficiently. I would say that I implemented it very successfully at Microsoft. And then I re-implemented it at Sprinklr.  It’s been something of a joy to behold.

The third theme is technology. When I started my career at Procter and Gamble, the world was not digital and connected as it is today. I could feel it coming and I had a strong interest in it. I was on Gopherspace, an early version of the web. Recently I found a presentation in an old filing cabinet I had done in 1993. It was about the upcoming cyber world. The presentation was very prescient in that it called out how technology will help us build new communities, and all the things that we live out today. I remember doing the presentation and I remember people at P&G thinking it was ridiculous. It will never happen, they told me. But it did. I love being very optimistic and future focused. Marketing has become a much more technical discipline over time. Being a technologist in marketing has proven to be a real advantage for me. I’ll always be excited about the new and latest things that come out. 

The three themes that have driven my career are people, process, and technology.


Each of the four major periods of my life taught me lessons that I still carry with me today. The first lesson was vital and it’s one that I don’t think enough people practice. 

I started my career at one of the world’s greatest companies, Procter and Gamble. I was 21 years old, right out of school. I went straight onto Tide and they gave me a massive budget to manage. My father was in advertising. He had this advice: “go find the librarian and get everything you can from that person.” I started asking around, then called my dad back. There was no library at P&G, and they didn’t have a librarian. My father clarified: of course there’s no library, but there’s a person at the company – guaranteed – who functions as a librarian. There’s someone there waiting for you to go ask them what Tide did in 1965. 

I continued bumping around and asking until finally someone said “You should talk to Tom Penhale.” Tom was a longtimer in promotions. He’d been squirreled away in a corner as the waves of change washed through P&G through the years. I introduced myself and said I was told he might be able to tell me a few things about the history of the company. Here’s what he said: “I’ve been waiting for someone like you to come along.” Tom had every promotion review and brand review for every brand going back to the early 60s. There were binders and binders. He had every single ad that P&G had produced since 1949 when it did its first advertisement. There were walls of three-quarter-inch tapes.

My colleagues at P&G were all people my age and we were all living our dream jobs. We’d work all day then go to dinner together in the evenings. At night, after dinner, I’d go back to the office to work through the treasures Tom had shared with me. I read all the documents. I studied every single recommendation. I watched the old commercials until I passed out. I did that every day for years. I ended up seeing every single commercial P&G had ever produced. That had such an amazing influence on the way I made recommendations and how I referenced things. It helped my advertising judgement because I got to see all these ads and because I also had the benefit of hindsight, I knew which ones worked and which ones didn’t. 

Studying history is something that not enough people in marketing and advertising do. Every profession – legal, medicine, you name it – knows their history. They also know the latest but they’re well versed in their history. Somehow in marketing and advertising we think we can get by with just knowing the latest, and forgetting about the history. That’s a mistake of negligence. 

In marketing and advertising we think we can get by with just knowing the latest, and forgetting about the history. That’s a mistake.


The second phase of my career began when I left P&G to become a web entrepreneur. I did five startups over the course of a dozen years. These years were characterized by amazing successes – absolutely incredible moments. There were also death-defying failures. And sometimes these two things happened within reasonably close proximity to one another. What I learned in that phase is that if it doesn’t kill you it makes you stronger. 

I became fearless. I realized that nothing really terrible is not going to happen to me if something does not work out. Sure, making mistakes does not feel good. And it sometimes takes time to recover when they leave you battered and bruised. But the turbulence in these years made me more comfortable with risk. They helped me recognize that no matter how bad things seemed, I would be fine and something else would come along. 

Risk taking is an important element in keeping your career alive for a long time. People who don’t take risks see their careers end earlier than they should.


The third phase of my career was the 12 years I spent at Microsoft. I started at the company in Research and worked on the early versions of their cloud products. I went on to become the CMO of Microsoft U.S. I was in that role for seven years and I loved every minute of it. It is one of the best jobs on the planet.

I was at Microsoft during a very interesting time in that company’s history. The lesson I took away from there is that companies can reinvent themselves. You have to believe in that next phase. It’s amazing how Microsoft has changed. It has leaped into its third business model. The real story of how that happened has not yet been fully told. There are books that have yet to be written about how Microsoft makes that transition. 

That experience taught me that reinvention is possible. Rebirth is possible. Even when everyone is calling you dead, you’re not. You don’t have to be. You can turn it around. You can make a difference and you can get back to where you want to be. 

Even when everyone is calling you dead, you don’t have to be. You can turn it around. You can get back to where you want to be.


The fourth stage of my career is the one I just started when I came to Sprinklr three years ago. I call it my unicorn years. But even mythical creatures can not evade the fundamental lesson this era has for me  and put into words by Peter Drucker, “culture eats strategy for breakfast.”

I’ve had the privilege and pleasure of working at companies with very strong cultures. When you walk into a company where the culture has been broken you sense it immediately. It’s amazing how hard it is to get anything done once this has happened. The threat to the business is so profound it’s existential.

I’ve been blessed with an incredible partner here at Sprinklr, Diane Adams, our Chief Culture and Talent Officer. Marketing and HR have locked arms and combined forces to work together on culture. It has been an amazing journey for me. Even when culture is broken, it can be fixed. It can get turned around. The company can get back on track. I’ll always respect culture, wherever and whenever I am.

Grad has personally experienced and lives by the famous Peter Drucker quote,

Culture eats Strategy for breakfast.


As humans, we’re the only animal aware of our own mortality. This awareness has a significant effect on us. It fuels creativity and drives us to live beyond ourselves. Tom Penhale, the librarian at P&G, sadly passed away some years ago. And yet he still lives in me because of the gifts that he gave me.

There’s a quote by Ralph Waldo Emerson that inspires me: “To know even one life has breathed easier because you have lived. This is to have succeeded.” For me, the recognition of my mortality is about doing things for others that can carry through time in the same ways. I’m very motivated to pay it forward. As others have already paid it forward through me.

Bob McDonald is one of these people. Bob loved leading people. Bob and I had different working philosophies when our paths crossed early in my career at P&G. I needed to love my product. He was the opposite. He loved leading people and it didn’t matter if the product was nails. I didn’t really get what Bob was teaching me until later when I made some mistakes with people and suddenly I understood what Bob was talking about. He went on to become the CEO of P&G and Secretary of Veterans Affairs and achieve amazing things in his life. The rewards he’s had stem from his incredible obsession and his commitment to his people. You scale yourself as a person when you bring others with you. Bob taught me that.

Tim Penner was my first manager. The lesson I learned from Tim came out of a mistake I made – a $15M mistake. I was 27 or 28 years old and I was prepared to take accountability for it. I told Tim if he wanted my resignation he would have it from me in the morning. His response: “Are you kidding? I just invested $15 million in your career. You’re not going anywhere.” Through Tim I learned how to view massive setbacks that are your own making as investments in your growth.  And I learned by Tim’s example on how to walk with grace when someone on your team makes a big mistake that creates a setback for you.  

Fernando Aguirre, who ended up becoming the CEO of Chiquita, was my manager when I was on Cheer. He taught me a ton about people management and the strategic value of a well thought-out budget. I said something stupid at one point and Fernando got so angry with me. He laid me out on the floor. I never did that again. And I probably would have done it again if I hadn’t had someone like Fernando in my life. It would have been more fatal. When it was done he checked in with me. We were good. And we went back off to work. I benefited from that lesson for the rest of my career.

Peter Neupert is an entire master’s course in the software era, technology, marketing, and positioning all rolled into one giant ball. He hired me into Microsoft and is a dear friend that I love very much. Sean Nolan who was my engineering partner at Microsoft. Sean was very instrumental in helping me navigate the organization.

There’s one other person I should mention. I haven’t talked to in a long time. The reasons for our falling out are not necessarily important. His name is Dr. Don Nightingale and I learned a lot from him. He was my client for many years and we spent a lot of time together. He was very thorough and academic in his thinking but very quick in his exchanges. I was presenting to Don in my P&G-trained ways, explaining how the work was on brand character and met the strategy and objectives goals. It was clear he hated the work. His feedback was this: “The only problem is that it doesn’t meet the strategy of me liking it.” It was a powerful lesson. You can’t get someone to buy something they don’t like. While I haven’t talked to Don in years, I still quote him all the time.

There are many others. I’ve been very lucky to have some amazing people in my life. 

The recognition of my mortality is about doing things for others that can carry through time. I’m very motivated to pay it forward, as others have already paid it forward through me.


One of the great, centering, and relaxing philosophies is this: Everything in life takes two trips. We live in a world that has so much complexity and for things to get done they usually require two trips. Whether you’re getting a new internet router installed or you’re really trying to get anything done in the modern world, you can expect hiccups. It’s very hard for things to just happen correctly because there’s so much complexity. Most people get super agitated by this. You probably know these people. They’re in a constant state of tumult. Most things are two trip tasks. Sometimes it’s three trips. And sometimes it’s one trip. But If you get a one-tripper, it’s just compensating for the three-tripper that’s coming down the tube. 

Start noticing this in your life. I think it’s a tweak in the matrix. Two trips is a way of testing people. I think it’s a way of separating the calm from the agitated and eventually separating the sane from the insane. When you embrace the two trips philosophy it’s very relaxing.

Life is about expectation management. If your dream is to live in a mobile home and you finally get to a mobile home, you’re going to be a very happy person. If your dream is to live in a castle and you’re living in a mobile home, you’re not a happy person. There are happy people in mobile homes and there are sad people in mobile homes. There are happy people in castles and there are sad people in castles. 

You’ve got to surround yourself with the people in your life who are happy. I have the world’s most amazing executive assistant. Her name is Sabrina. She has had some pretty challenging things happen to her, like all of us. Maybe some of hers were a little more challenging than mine or yours. But 24/7 she has a positive attitude. When you find people like that, keep them very close to you. Don’t let them out of your sight. These people are rarer than they should be. Positivity is extremely powerful. When things go well, these people are amazing. When things don’t go well these people keep things under control.  

Positive people are rarer than they should be. When things go well, these people are amazing. When things don’t go well these people keep things under control.


My children are doing what they told me they wanted to do when they were five years old. They’re both in highly specialized careers, achieving at levels that are very hard to reach. Supporting my daughters in their journeys is without question the greatest thing I’ve ever done. 

One of the biggest mistakes I think parents make is telling their kids they always have to have a Plan B. That’s a terrible mistake. Tell them to follow their dreams. Go all in. There’s no Plan B. When they have a Plan B they don’t have the focus to give everything they’ve got to their dream.

Achieving dreams requires a lot of support. You’ve got to keep throwing logs on the fire long after they get out of university. The hardest question for parents is “can I support them long enough to get the traction they need to get to the next level?” A lot of parents stop investing too early in their kids. And they give their kids too many options. I say burn the bridges as fast as you can. There’s no Plan B. Follow your dream and go down the path you’re meant to go because otherwise, they’ll end up in marketing. Somehow lots of people end up in marketing because it was their Plan B.

There’s no Plan B. Follow your dreams.