Forget the 5-Year Plan — Here's How to Find Your 20-Year Plan, According to a CMO

In today’s age of celebrity-status entrepreneurs, it seems there’s a new success fad making headlines daily. But when different, conflicting strategies are being promoted at every turn, knowing which formula to actually follow for professional fulfillment can feel tricky.

That’s why Jody Kaminsky prefers to keep things refreshingly simple. Her recommendation? Do one thing, and do it well — and if you love your job, don’t leave it.

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The latter may seem self-explanatory, but in today’s age of job-hopping, staying for more than two decades at the same company is pretty radical. Or it would be, if you didn’t work somewhere like Ultimate Software. Kaminsky, who’s been Chief Marketing Officer for 10 years and a member of the Ultimate Software family for 20, says she’s actually one of several colleagues to make this company their extended home. Recently, she spelled out for Fairygodboss how exactly she found a work culture worth staying at, as well as her No. 1 piece of advice to women who wish they could say the same.

How long have you been with your company? What about it made you first want to join?

I started with Ultimate Software in 1999, so next year it’ll be 20 years. We love celebrating anniversaries at Ultimate, and you become a “Legend” at 20 years. We have quite a few Legends, which is especially impressive considering the company is just 28 years old! 

I remember walking in for my interview and being blown away by the culture Scott Scherr and his team had nurtured. We were a small company back then, and there was a strong sense of connection, dedication, passion – of family. I knew immediately that this was where I belonged. We’ve grown substantially in the past 20 years, but our culture’s never changed because we go to great lengths to sustain and grow it.

Tell me about the roles that you’ve held at your company, as well as your current one. What about this role most excites you?

I’ve been in my current role as Chief Marketing Officer for 10 years. However, during the past 20 years I’ve had the opportunity to work in a number of different roles within marketing. It has been an exciting time of experimentation and growth, and I was included in important strategic initiatives right from the beginning. 

I love marketing because it’s a beautiful intersection of strategy, relationships, and data. I’m grateful for the opportunity to share Ultimate’s story, but if I had to choose one thing that excites me most, it would be seeing the successful growth of Ultimate and its brand over the years. It is my honor to be a part of it. 

What’s something you’re especially good at at work?

Identifying and tailoring content to your audience is a crucial business skill. You can’t use the same speaking style or emphasize the same things when you’re talking to prospects, investors, your team, your boss. Each situation requires a different approach. I think it is important to familiarize yourself with your audience, and vary tones and motivators depending on who you are speaking to.

I recently spoke to an inspiring group of successful female executives about the importance of growing your professional brand, establishing yourself as a leader, and tying your personal brand to your employer’s. Those topics would also be helpful for women early in their careers, too, but the examples and suggestions I used would need to be tweaked to have the greatest impact. Evaluate your audience, figure out their needs, their goals, their pain points, and customize your messaging to suit that. 

What’s the first (and/or last) thing you do at work every day? 

Efficiency is very important to me. I usually begin my day reviewing my calendar and making a mental list of the highest priority items I need to accomplish and look for opportunities to combine tasks/goals. It’s certainly not ground-breaking, but it keeps me grounded.

A lot of people believe that developing your career means changing companies, and not infrequently. What has enabled you to develop/advance your career without job hopping?

My CEO, Scott Scherr, always encourages us to “keep the main thing, the main thing.” For me, that main thing is marketing. I’m passionate about the company we’ve built, the culture we’ve nurtured, the product we’ve developed – and I’m equally passionate about sharing that message with the world. I truly believe that when we share our story authentically, it resonates with people and helps them improve their own workplace. This passion has not only made me infinitely better at my job, it’s also contagious, and it’s opened doors that otherwise wouldn’t have existed for me. 

Ultimately, what has led you to stay at your company?

Ultimate’s award-winning culture is as much of a draw today as it was the first day I walked in. In fact, our employees now enjoy substantially more benefits than ever before, thanks to our brilliant Chief People Officer, Viv Maza, who makes it her personal mission to touch as many lives as possible. As an example, Viv recently collected donations for the victims of Hurricane Michael, as well as for the family of an Ulti employee who tragically passed away. As always, the company matched every dollar our employees contributed.

Viv and Scott are incredible role models, leading by example and epitomizing what it’s like to be a selfless leader. I’m incredibly proud of the products we’ve developed, the services we provide, but most importantly the difference we make in the world – in the lives of our employees and their families, in our local communities, and our contributions to improving the future of work. 

What’s something you think most people (perhaps even current employees) don’t know about your company that you think they should? 

Ultimate Software started with just four employees, two cubicles, and a dream. We’ve become a major player in the HCM market, but we’ve never forgotten our humble beginnings and the passion for a better solution that inspired Ultimate’s creation in the first place. 

What was the best quality of the best boss you’ve ever had?

It’s tough to choose just one of his qualities, but I’ll go with authenticity. Everyone from new hires to analysts to prospects marvel at how genuine, humble, and real he is – Scott Scherr keeps his promises, tells the truth, and holds others accountable to do the same. When you’re in the same industry for a long time, it’s relatively easy to detect when someone is being inauthentic. I’m coming up on my second decade with Ultimate, and I’ve never seen that in Scott. Not once.

What’s the most memorable piece of career advice you’ve received?

The advice that ultimately inspired our tagline: Put people first. Scott always believed that if you take excellent care of your people, they’ll take excellent care of your customers, who will in turn take excellent care of your bottom line. This advice has made us a “Best Place to Work” multiple times over, it’s made us a billion-dollar company, and it’s made me a leader who always prioritizes what’s best for my people.  

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