The role of the chief marketing officer (CMO) has evolved as companies digitally transform, embrace the power of brand, and lean into data-driven behavioral insights to drive client growth and satisfaction. No longer is the role merely “colors and fonts” or “clever copy.” Today, a CMO sits at the intersection of most functions within an enterprise, with responsibilities that span pipe, business development, sales automation, and even community-building. As a result, successful CMOs must embrace change while remaining close to both customer and product.
Jim Sinai is a seasoned cloud executive and experienced marketer, with a background in sales and business development. He is passionate about new technology, telling the story, and helping make complex software easy to understand.
Jim Sinai on Jobs & Careers
Jon Fee: What do you think is the difference between a job and a career?
Jim Sinai: A job is what you do in a moment or period. A career is the portfolio of jobs that defines your identity. I started in software in customer service, moved into sales, and have spent the last decade in marketing. So I think I will probably look at my career as a software executive more than the job or role I held. I also am a big believer that we live our lives in chapters. Chapter one was service and sales. Chapter two was marketing. I’m curious what chapter three will be.
Fee: Well, tell us a bit about the prelude to chapter one! What was your first job?
Sinai: My first job in high school and summers in college was working on a construction job site as a laborer. My first job out of college was in a call center at Bloomberg. While these may seem very different, there was a common theme – both roles were manic about customer service. My job every day in construction was to make sure the homeowner/client’s house was dust-free and they felt that the construction project was minimally disruptive. And at Bloomberg, it was grounded in what customer service at scale needs to look like.
Fee: That’s really interesting! What was your first job in marketing and what’s something you learned from an earlier job you had outside of marketing that impacts your approach to marketing?
Sinai: My first marketing role was as a product marketing manager on a small business unit at Salesforce in 2011. There are two things that really made me successful in product marketing. The first was that I came from sales so I always looked at my marketing through the lens of “would i say this in a customer meeting?” The second was that I really wanted to be a product manager for a period. This allowed me to really lean into the product side of the role and understand how software is built. Both of these perspectives have continued to inform how I approach marketing in my role at Vanilla, where we’re reinventing the estate planning experience by building beautifully designed products that make the complex simple.
Fee: Tell me about how marketing was defined when you first entered the field vs how you as a CMO define it today?
Sinai: Since I started in marketing, there’s been an explosion of technology and data, creating a more data driven approach to marketing. But lately, the amount of data and systems are starting to be too much for an organization to really leverage. AI is most definitely going to make managing data easier. Lately, I’m noticing a trend of the best marketing organizations returning to the power of storytelling and brand to build and maintain their differentiation. So, while the tools and channels might change, the core focus of great marketing – be something special to someone – is not going change.
Jim Sinai on Pets and Pet Peeves
Fee: Do you have pets? What about Pet Peeves? What annoys you the most in the workplace?
Sinai: Three kids keep us plenty busy so we are going to wait a beat before adding a fourth “kid” to the mix. My wife is a veterinarian so she gets the rest of her dog fix at work.
But I do have a few pet peeves. I really get annoyed when someone calls a meeting and doesn’t come prepared to drive the conversation. I’m not saying you need to have a full deck, but you should be driving the conversation and making sure it’s outcome oriented. Second, I think a lot of people forget to set context for executives. We’re all busy so it’s important to start with 30 seconds of “why are we here” and “what decision do we need to make?”
Leadership and Work Habits
Fee: What’s the one thing you can point to (a book, an experience, a person) that has played the greatest role in shaping your leadership style?
Sinai: Early on in my career I learned about the Nordstrom organization chart, which is upside-down. It’s the CEO’s job to support the management team and the manager’s job to support the associates in the store. That has always resonated with me and how I approach leadership. The marketer in me loves the book “The Power of Moments” by Chip and Dan Heath. They point out how to create lasting impressions with people by wow-ing them when their brain is primed to take inputs
Fee: One of my favorite questions to ask other CMOs – define digital transformation without using the word digital or transformation.
Sinai: Is it cheating if you use a foreign word? Kaizen is the Japanese word or term for continuous improvement. Most every organization practices kaizen to some degree, albeit some slower than others. And continuously improving is about adopting both proven and innovative practices from other industries to better serve your customers and employees. As long as everyone can agree the status quo isn’t sufficient, we’ll all continue to get better!
Fee: Tell me about your volunteerism and giving back to make a greater impact?
Sinai: I love to volunteer when I can. Truth be told, it comes in waves and right now I’m in a trough, mainly due to intense family commitments. In the past I’ve spent time as a youth mentor or tutoring in schools. But right now, I’m spending time coaching young kids on the soccer and baseball field. Everytime I lean in, I remember that giving back is one of the best ways to create happiness and joy.
Careerwise, I know I always prefer to be working on a product that has an element of giving back. At Bloomberg and Salesforce, employees were measured on volunteering. At Procore, our platform was improving how folks on the jobsite worked and we delivered countless dollars and hours of free training and products to university students. And now at Vanilla, we are working on how to simplify estate planning, first for the advisor community, but ultimately to make it more accessible to everyone.
Fee: Have you ever been on the receiving end of giving, and how did it impact you?
Sinai: Every role I’ve gotten, from admission to a school or a job offer, has come because of mentorship and network. I’m super indebted to folks who gave me time and the opportunity. So I take it as a mission to make sure to help the folks coming up find their way to their opportunities.
Looking into the Crystal Ball with Jim Sinai
Fee: Tell me about your predictions for marketing and marketers? What’s coming next? How do we prepare?
Sinai: I think we’ve seen just the tip of the iceberg on generative AI so I’m loath to predict what the future holds. One thing I can say for sure is that it’s going to be easier and easier to generate content which means that while more marketing teams can focus on creating more content, it’s going to require more work to cut through the noise. I’m also curious to see how search changes when we get to more conversational user interfaces.
Jim Sinai’s Parting Gift
Fee: Can you share with us an album, book, movie, TV series, or other creative work that brings you joy right now? What is it about this creative work that fires you up?
Sinai: I’m in the middle of Shantaram. It’s about an Australian escaped-convict hiding in India. It’s a long read, but I’m enjoying getting a peek into a culture I know little about.
And let’s also just admit that Netflix’s Drive to Survive was the world’s best marketing stunt. I am shocked to admit I’m now an F1 fan.
To stay connected to Jim, you can follow him on LinkedIn.