CEO Scott Scherr Leads Inclusion in Tech

A tech company that truly puts People First is not a glitch. It’s the result of the deliberate work of its founder and CEO Scott Scherr. In a business that provides HR solutions, Ultimate Software sets the example by taking care of its own associates first.

RSM Hall of Fame

When in 1990 Scott Scherr founded Ultimate Software with three other people (two of them women who still work at Ultimate,) they decided one of their key priorities would be to take care of their employees. It’s proven to be a winning strategy judging by the long-term profitability of the company, their enviable 94% employee retention rate and the recurrent recognition as one of the best companies to work for. (Forbes, Fortune, Glassdoor, etc.)

Among his many leadership qualities, Scott has always stood up for inclusion of all kinds, paying particular attention to gender inclusion at the top. He’s fostered a culture of listening to people’s needs and taking quick action even when it meant changing a policy to accommodate one associate’s life’s circumstances.

For his commitment to improving the workplace for 100% of the talent, we honor Scott Scherr with the 2019 Hall of Fame.

Red Shoe Movement — What are some of the key traits of a great leader?

Scott Scherr, CEO, Ultimate Software

Scott Scherr — I was brought up in a small family business led by my dad, Reuben Scherr, and I saw first-hand how to lead by example and “walk the talk.”

The core values I learned, whether working with my family or coming up through Corporate America, were the same: treat everyone with dignity and respect. As a leader, take care of your employees. They’ll, in turn, take care of your customers, and the company will thrive.

We founded Ultimate Software 28 years ago on this principle, with a commitment to always put people first. “People First” is more than a mantra. It’s an ethos our more than 4,700 employees embody every day. It drives how we care for our people, design our HR technology, and serve our customers.

As a kid, growing up in the Bronx, I loved to play baseball, basketball, and soccer with my friends. Whenever it came time to choose teams, I always got to be a captain who hand-picked my players. I knew then, and I know now, how important it is to pick the best team and to motivate them to do their best.

I believe the key to Ultimate’s success is the strength of our team—the people who lead and inspire me every day. To symbolize the trust and respect I share with every employee, I give all our people a card with the word “Trust” on one side and “Forever” on the other when they join our team. The idea came from when I met a longtime role model, legendary basketball coach Pat Riley. Pat had given his players similar cards to reinforce the unconditional bond among the coach and his team.

I feel a similar bond of lifelong unity within our Ultimate family, a phenomenal group of leaders I’m honored to work alongside daily. This bond extends to our 4,400 customers, and many now have Trust cards (which I give out at our annual customer conference, Connections), symbolizing our lifelong partnership together.

Scott Scherr talks to a group of employees

RSM — Why do women make great leaders? 

SS— Ultimate transitioned from a four-person start-up, two of whom were women, to a publicly traded company with more than 4,700 global employees. I’ve witnessed stellar leadership first-hand, starting with my founding colleagues, Vivian Maza and Debra Sasso, both of whom are still with our company to this day, 28 years later. Today, women comprise nearly half (49%) our total workforce, and about 50% hold frontline manager positions.

I don’t believe Ultimate would be as successful as we are today without the unique abilities our female leaders bring to our organization. They’re relentless and innovative in problem-solving. They inspire others to achieve high performance. They collaborate and communicate effectively to make the lives of our employees and our customers better.

For example, Ultimate’s Women in Leadership (WIL) is a companywide group that’s flourished in helping women at all levels of our company achieve their maximum potential. At the same time, WIL encourages women to discuss their goals, ask questions, and collaborate with one another on ways to positively impact future female leaders at work, school, and in the community. WIL has over 65 sub-committee members throughout the United States and Canada and will host more than 90 seminars, workshops, philanthropic outings, and networking events this year.

Don't miss the interview with Hall of Fame 2018 Andrés Graziosi of Novartis

Scott Scherr inspires his team daily with his strong, inclusive vision.

Hear Scott Scherr’s recommendation for approaching your CEO

RSM — How open is your door for your associates to approach you and what’s the best way to do it? What do you expect people to come with when they ask for a few minutes to see you?

SS — From the beginning, I’ve always had an open-door policy and answered my own phone. No matter their roles on our team or how long they’ve been with Ultimate, I want to hear their ideas. I value their feedback and hope to answer their questions and address any concerns.

Listening is vital to any organization, and it’s been key to Ultimate’s success. When our people meet with me, whether in small groups or one-on-one, I’m there to listen. I try to put myself in their shoes. I recognize it’s not always easy to talk with a CEO, but we’re all people and should treat one another with equal respect, value, and care.

When you have the opportunity to meet with company leaders:

• Bring a Thought-Out Plan: Always know the purpose of your meeting and what you’d like to discuss or accomplish.
• Be Clear and Concise: Discuss a specific product, service, or organizational issue, and how it impacts you, the company, and your customers.
• Research Your Ideas: Learn how this might impact the big picture, and the company’s place in the overall industry. What do customers expect. What are competitors doing?
• Offer Solutions: If you disagree with how something’s done, provide a new method that can lead to more efficiencies or greater success.
• Remain Open to Change: Accept constructive feedback. Be willing to discuss how the entire team can build upon your idea. The outcome might look different than the original. Be a team player. Offer ways to collaborate with others to achieve goals.

Scott Scherr keeps an open door policy

RSM — What would you say are the key ways to make people feel like they belong to your organization?

SS — One of my favorite affirmations is “Everyone, Every Day.” This reminds me to always care for, respect, and trust everymember of our organization—and to treat every colleague like family.

From early on, even when Ultimate struggled toward profitability, I made the commitment to pay employee medical and dental insurance and provide everyone, from the receptionist on up, with equity in the company. This is our business. We’re all in it together.

Today, our company is thriving, and we’re about to reach our next championship milestone of $1 billion in revenue. I’m proud that Ultimate still offers 100%-paid healthcare premiums for all employees and their families (including same-sex couples). We also have a 40% dollar-for-dollar 401(k) employer match, with no cap; unlimited personal time off for all exempt employees; annual service days for volunteering in the community; and generous paid maternity, paternity, and adoption leave policies.

Ultimate’s goal is to value the whole person, emphasizing a work-life balance that fosters individual professional growth and development while supporting personal pursuits. That makes Ultimate a company where, we feel, everyone has a sense of belonging—a sentiment that’s illustrated by our 94% employee retention rate.

RSM — In your experience, how does having a diverse and inclusive team of executives impact your bottom line? 

SS — “Walking the talk” in a “People First” culture means we care for and treat all people equally. I believe that, by celebrating individuals’ unique qualities, experiences, and backgrounds, we can all learn a lot from one another and continue to strengthen Ultimate as a whole.

Our family-like culture welcomes all people, and we encourage our employees to bring their whole selves to work. We illustrate that commitment with our companywide Communities of Interest that support LGBTQIA individuals, women, veterans and active service members, and cancer patients, survivors, and caregivers.

Our teams and leaders come from diverse backgrounds, with nearly half of the highest-level management positions on our Software Engineering team are held by people from Canada, Colombia, Dubai, India, Romania, and Puerto Rico, making Ultimate a true melting pot.

I believe these differences define who we are as individuals and make us stronger and more successful as an organization. In Q2 2018, we reported $239.5 million in recurring revenue, up by 23%, and total revenues of $271.2 million, up by 21%. These results are in no small part due to our diverse, inclusive workforce. Our diversity makes Ultimate an inspiring, empowering place for anyone and everyone to work.

Scott Scherr Take Your Kids To Work

Scott Scherr helping promote more women in tech

RSM — As a leader, what are you specifically doing to level the playing field for women in technology?

SS — I believe any team’s success is based on “we,” not me. A company can only achieve its maximum potential if we create a culture that supports and empowers women as technologists, innovators, and leaders.

I greatly value the card we give every new hire, and to our customers. As I mentioned it has the word “Trust” on one side and “Forever” on the other. Every person joining Ultimate—from the first two women who helped me launch the company in 1990, to the more than 4,700 people with us today, including our original two—they’re all members of our Ultimate family, “Forever.” You should feel that inclusion in any organization.

We trust in the talent, innovation, and creativity of our people to make our products and services better every day. My job is to support programs that help us accomplish this.

Our TechStars internship program brings college students and recent graduates onto our development teams. They gain firsthand programming experience, develop their coding skills, and foster personal and professional growth through mentoring.

We’re extremely fortunate for what we’ve built at Ultimate. We pay it forward every year through programs like our Athena Scholarship. We award two college scholarships (up to $20,000 each) to graduating daughters or high school seniors of our employees. These scholarships make it easier for young women to pursue studies in technology and leadership.

Most recently, we introduced Unlimited PTO, to give employees greater flexibility in their work-life balance. They use the time to travel, recharge, or to care for children, parents, or loved ones. This goes back to my commitment of “Trust” and “Forever.” I trust our employees and respect their whole selves, not just their work. It’s a forever commitment from me, on behalf of Ultimate.

I’m proud our commitment to female technologists was recognized by AnitaB.org. This means we’re “walking the talk” in leveling the playing field for women in technology.

RSM— In terms of leadership lessons, is there a particular mistake or failure that you now “cherish” because of what you learned from it?

SS — Nearly 30 years ago, I took a leap of faith in leaving one of the top HCM providers at the time. I enlisted three colleagues to make the jump with me. We started Ultimate Software with two cubicles, and a shared “People First” vision.

I raised our initial funding from a group of peers. I believed in our company and what we were trying to do. I’m grateful for those who embraced Ultimate’s vision and got us off the ground.

It hasn’t always been easy. Throughout our history as an HR software company, we’ve faced great challenges. I call these “thunderbolts.” We’ve seen tough financial times, like when our stock price dropped to $2 a share. I felt tremendous pressure to keep the business moving forward.

In 2002, we made the strategic decision to become our industry’s first Software as a Service (SaaS) provider. It was a risky choice, but I believed this would help Ultimate reach a new level, better able to serve our customers while bringing on new business.

When you face thunderbolts, keep a clear vision. Remain relentless in execution. Stay true to your values and “non-negotiables.” (I refused to waver on healthcare coverage for our people, even when investors questioned the expense).

No matter your industry or business, you’ll have challenges. But it’s during these thunderbolts when you’ll likely do your best work and achieve your greatest success. Great teams are the ones that persist through adversity. They’re focused on one, primary goal as a team. They build upon individual strengths and contributions to reach their objectives—together.

As a company, we’ve seen lows. But when others called it the end for us, we remained strong. We remained committed to our people, and to our lifelong promise of putting people first (employees, customers, and the community). Today, we’re stronger than we’ve ever been. We’re about to become a billion-dollar company, and we have the greatest team of people to thank for it.

Scott Scherr takes a selfie. The organization feels like a big family.