A Conversation with Rocket Software CMO Jeff Winter

Living your values when times are difficult is crucial not just to organizational success, but also to creating a sustainable culture that can weather the toughest of moments. Right now is one of those moments, where great companies reveal what makes them exceptional.

As we navigate uncertain times, I thought back to a recent conversation our team had with Jeff Winter, the CMO of Rocket Software. Rocket Software has four core values: empathy, humanity, trust and love. But what does it mean to manage with those values? And how do you maintain a culture of love and accountability? Jeff had great insights on what he’s learned from Rocket’s values, and how it’s influenced his approach to leadership.  I think those values and his insight are especially relevant right now.

When you first heard about Rocket’s values, what were your thoughts?

I first heard about this when I was interviewing for the job. To say the least, I was surprised. Those aren’t words you usually hear from a Bain Capital-backed, hard-driving competitive software company in tough-minded Boston. But the more I got to know Andy Youniss, our president and CEO, and the further I got in the recruiting process, the more I started to believe. And in the five months that I’ve been at Rocket, I see these four values in practice every day.

What about when you joined the company?

Once I joined, I noticed these topics come up regularly during executive leadership team meetings. When we were contemplating last year whether (and how) to raise prices for some of our offerings, we debated and discussed how it might impact them; how do we do it; when; and, to the core of our values, were we actually delivering value to justify the price increase?

Here’s another example. We’ve been a very acquisitive company, having made 53 acquisitions since the company’s founding 30 years ago this month (Happy Birthday, Rocket!), and those philosophies govern how we integrate. We begin with empathy, and think about the expectations, experiences, and processes for each individual at the acquired company and from Rocket. Many studies point to the two key reasons why mergers and acquisitions fail: lack of cultural fit, misaligned expectations, and poor communication. We don’t get everything right all of the time, but using our values as lenses, we’re more likely to be on the mark than not.

Did you have to make adjustments to your management style when you joined Rocket?

I think from a love, humanity and trust factor I’m a pretty affable guy, and I’ve always been considered an outgoing people-person. I’ve always dedicated a lot of time to ensuring that my teams have development plans, and to mentoring and coaching individuals. These are all management and leadership values that Rocket believes in, and that I sort of had in my bag as well. So no big lift there.

But I’m a fairly hard driver and demand a lot of my teams. As a result, I sometimes move so quickly, whether that’s building or adjusting a team or wanting to put initiatives in place, that I sometimes underappreciate the value of empathy. I don’t take certain things into consideration as much as I should, such as considering how something will impact an individual or how it is going to impact an adjacent work project or program. So I’ve worked to appreciate empathy a little bit more than the other ones. And that’s so critical right now, especially with everyone’s stress levels being higher, workloads increasing as we adjust our plans, and managing the inefficiencies of working from home. We all need a little bit more empathy to get through this pandemic together.

How do you serve as an understanding, empathetic manager while also making sure things get done?

You have to give everyone on your team the tools to succeed and continue to make sure that they have those tools. Maybe that’s fixing an internal process that’s inefficient or finding a new software tool to help them do their job better. I think providing the budget, the resources, and the processes to help people do their job creates a culture of accountability that goes both ways. We had this before the coronavirus, of course, but with everyone working from home and still trying to work as a cohesive unit it’s more critical than ever. And people are really responding well to it.

Recognition is also really important. You want to recognize people, whether or that’s through a formal awards program, a public pat on the back, or giving supporting career growth and leadership opportunities. So having a team present to a vice president or even the CEO are great tools for building employee recognition. We all know that millennials and Gen Z employees want to be part of something bigger. They want to be part of a purpose-driven organization, and not everyone is always after money and compensation. It’s really about being part of a whole and being recognized and challenged with good work, but also getting recognized for it. I’ve always put in formal awards programs, and we’re already doing it at Rocket. Recognition is so important. And it’s so easy, it doesn’t cost a lot of money, it doesn’t take a lot of time, and people absolutely love it.

What are some other ways Rocket puts those values into action in the workplace and the community?

Rocket was one of the first large tech companies that mandated a work-from-home policy because of COVID-19. There was zero hesitation – we asked more than 1,400 Rocketeers around the world to not go to work to protect themselves, their families, and their communities.

We’ve made a few of our flagship products free for six months so that our clients’ tech teams can work remotely. These are products that, generally speaking, allow IT teams to monitor their systems remotely rather than go into an office or data center, which helps protect their health and prevent the spread of coronavirus.

We are also transforming our annual hackathon program, called “Rocket.Build,” to now target pandemic-related challenges across not only our customer base but into the community overall. We’re also participating in a number of industry-wide initiatives to help governments and other organizations use technology to get through the current crisis and prepare for the uncertain future.

When company values are well-defined and true to the way an organization does business, they can guide decision making, set your company apart from the competition and make it easier to recruit people that will be a good cultural fit. So … what do you value?