Jeff Winter of Rocket Software

      We Spoke to Jeff Winter of Rocket Software

      had the pleasure of interviewing Jeff Winter, SVP.

      Jeff Winter joined Rocket in 2019 as Chief Marketing Officer. He has more than 20 years of experience in the IT market in strategy and marketing roles, and was previously Global VP for Marketing and Communications for Pitney Bowes’ Software Solutions business. Reporting jointly to the CMO and President of the Software Solutions business, Jeff managed a cross-functional team across the Americas, EMEA, and APAC that was responsible for growing the software business, including products, solutions, and digital assets (APIs, data). Jeff was part of a new management team that returned the software business to consecutive years of growth, enabling the successful $700M sale.

      Prior to Pitney Bowes, Jeff spent 10 years at SAP in various marketing leadership roles, including serving as divisional CMO for the Professional Services business (globally) and running field, channel, and account-based marketing functions within North America. Before joining SAP, he spent five years in various marketing and strategy roles within IBM’s Global Services division. Jeff’s work on account-based marketing, customer experience, and new product introduction has been recognized by multiple industry awards, including two Sirius Decisions Program of the Year awards, and the IT Services Marketing Association Diamond Award for Excellence.

      Jeff holds a Masters of Business Administration from Emory University’s Goizueta Business School in Atlanta, Georgia, and a Bachelor of Arts from Skidmore College in Saratoga Springs, New York (USA). He grew up outside Washington, DC and has lived in Connecticut for the past 20 years with his wife and two sons. Jeff is a recovering triathlete, enthusiastic golfer, tone-deaf guitar player, and political wonk. Jeff also played professional basketball in Israel.

      Thank you so much for joining us in this interview series. Before we dive into our discussion, our readers would love to “get to know you” a bit better. Can you share with us the backstory about what brought you to your specific career path?

      I didn’t take a typical route when it comes to my career in B2B marketing. I truthfully didn’t know what I wanted to do. I majored in English Literature, but I ended up working on Capitol Hill and for a non-profit as I toyed with the idea of law school or a career in the public sector. After deciding there are too many lawyers in the world, but more seriously, having been exposed to aspects of marketing, I decided to earn an MBA with an emphasis in marketing. Once I received my degree, taking a marketing manager role at IBM was a no brainer. This ended up molding my career, setting me on a path for the last 20+ years into the world of technology marketing.

      I continuously ask myself three things when assessing a job I am currently in, or a potential career change:

      1. Am I working with smart people?
      2. Am I able to grow? Is it somewhere I can learn and develop?
      3. Sunday night test: do I have that uneasy, dreadful feeling Sunday evening as I think about starting another work week? If so, it’s likely time to make a change.

      The above are three principles that make me think about decisions in a different light and have helped me to reach my current position.


      It would have to be playing professional basketball in Israel. I came home from college and literally the day I got home, my mom told me there was a message on the machine from an American rabbi who was a big basketball fan. He partnered with a basketball agent in Israel to recruit Jewish American basketball players.

      I had played college basketball and had a reasonably solid career, and the rabbi somehow found out that I made a Jewish national all-star team. He and my college coach put together a highlight tape (look that one up, Millennials 😊), sent it to the agent, and off I went. I tried out with several teams; ultimately, signed with one, and boom — I was a professional basketball player.

      I spent a year living in Tel Aviv 100 yards from the beach; and it was an absolutely amazing experience. It’s not something I planned for by any means; it’s something I stumbled upon, but I am thankful and really happy I took advantage of the opportunity.


      When I was working at a non-profit in Washington D.C. focused on revitalizing the downtown area, I was constantly networking with different board members to get advice and counsel as I was just starting off in my career. I will never forget one of the Board members, Greg Fazakerley. I asked Greg if he would provide some career advice — basically to mentor me. So, we met for breakfast one morning and he was sharing his career path when he leaned back from the chair, took a pause, looked me dead in the eyes and said, “You can always make up the money, but you can’t ever make up the time.” He wrote that down on a piece of paper and to this day I have that piece of paper in my wallet.

      I don’t think about this every day, but whenever I’ve been at a career inflection point, thinking about changing jobs or companies, Greg’s words help inform my decision-making. For example, more than once at SAP, opportunities presented themselves, but for personal reasons, they didn’t make sense at the time. Sure, my decisions may have cost me some money in the short term and maybe too in the long term, but at the time it wasn’t right for me and my family. I don’t have any regrets, but I do come back to think about this quote at those inflection points in life.

      Is there a particular book that made a significant impact on your leadership style? Can you share a story or an example of that?

      There’s a lot of books, but one in particular: “Freakanomics.” The authors share the really surprising things you learn when you look at numbers.

      The authors take different hypotheses and really dig into the data. Basically, it’s the idea that data can be interesting, surprising, and even counter-intuitive. This really clued me into how important numbers are in statistics and analytics.

      I’ll give you an example from my SAP years. At the time, I was running an account-based marketing program for the top customers. We were in the process of setting up metrics around how we were going to judge the success of the marketing investments — Sales often uses a pipeline multiple of 3X. Meaning you always have to have a pipeline three times bigger than your revenue target in order to achieve the target. However, with this particular customer set, you don’t actually need that 3X multiple. Having of mix of loyal customers and those that spend at a certain threshold requires a different set of metrics.

      As a result of looking at the data and determining what we actually needed in terms of the multiple, it ended up being around 1.5X. This ended up changing our entire approach for the account-based marketing program about where we could put our efforts. This great insight came from someone asking a very basic question: is it true? Looking at numbers and data is important, and the marketing profession is now numbers and quantitatively driven, you really have to have to think critically about data.


      That’s pretty easy to answer. Yes, we have quality products that help our customer run their mission critical processes. But what truly sets us apart is our values: empathy, humanity, trust and love. I often tell the story of when I was interviewing with Rocket Software as this was the first time I heard the CEO, Andy Youniss, speak about these values. At first, I thought these were just a flavor of the month or some corporate tagline that would change within the year, but that hasn’t been the case. These four values are real and here to stay.

      These really differentiate Rocket as a software company, but even more directly, I think it differentiates us against some of our top competitors. We really do treat our customers in a different way.

      During one of our first executive leadership meetings, with a mostly brand-new team, we were talking about potential new revenue streams. We discussed the topic of maintenance. You see, most software companies have multiple tiers of maintenance support. Basic, Premium, and the like. At Rocket, there is only one tier. The question was raised about should we have a second tier. Our CEO was perplexed at this question. He didn’t really even know how you could ask this question. I came from SAP, where we offered four tiers of support, so this made sense to me, but for our CEO, he didn’t get it. He didn’t understand how we could not support a customer in their time of need. He — and all of Rocket — believes in treating every customer well, and treating them all fairly, as equals, so that the Rocket values are exemplified. We have to help every customer. This was an example in my career about how you apply the values to business.


      I would say two things. First, don’t put too much pressure on yourself to find THE career immediately. Figuring out what you want to do for the rest of your career in year one is an unrealistic expectation. It creates so much stress, angst and anxiety. Careers are different now as we’re in a gig economy and stints at companies often last just two-three years. There’s no more company pensions or loyalties of the 20th century.

      Our approach as individuals should change as well. We need to realize we have to take different paths in our career, and it might take you a few tries to get to where you want to be. For me, I went from pro basketball, to a legal career to one in the public sector, before ultimately finding my passion in marketing in my late 20s. Now, if you are fortunate to find your ultimate path early on in life, that is great. But for many or even most of us, it takes time. Enjoy the ride and learn along the way.

      It’s also important to have a framework around how you approach your career and to be intentional about what that framework is. I’ll always reference those three questions discussed earlier. Having a solid framework developed early in your career, will help lead you toward your ultimate goal.


      I was chatting one day with my cousin, who was in law school, about career choices. I asked what he was going to do after law school, presuming he would work as an attorney. Surprisingly, he said he wasn’t sure, and ended up pursuing a career in business. In that same conversation, he suggested that I go to law school as it “couldn’t hurt.” I thought to myself: Three years of hard work, and a lot of money for something I didn’t KNOW I would pursue? Needless to say, I did not take that advice and am most grateful for it.


      One is being team oriented and willing to go across organizational boundaries. Especially if you’re in a global organization, you’re always partnering with different levels of relationships with different functions, but there’s hardly anything that you can do end-to-end without help. You have to be able to work across boundaries.

      When I was at SAP, which makes its money on selling software, I was running the marketing team that supported SAP’s professional services business. Services was part of the revenue model, but certainly not the core of it. I was always kind of the guy banging on everyone’s door saying, “Hey, what about me? What about services?” It took a lot of work and persuasion in order to get people to respond and engage. Having this orientation for an end-to-end view of how we can serve customers and how we can generate more total revenue for the company as a whole was really what I brought to the table.

      The second trait is transparency. There are different types of transparency, but generally speaking, having the ability to have an open conversation with your team, your leaders and your direct reports is incredibly important. It shows that you have trust in them, and that you’re empowering them. Being transparent also demonstrates a sense of vulnerability. You have the ability to be transparent to own something that might not have been the greatest idea. I also really appreciate when people are transparent with me, regardless of what their role is. It really allows us to show that we are all human beings.

      Lastly, you have to be results oriented. You can be the nicest person in the world or the most persuasive person, but you need to show results. There are definitely different functions where it’s easier to show results versus others. For example, sales teams are given a target each quarter, and they either achieve it or they don’t. It’s very transparent for certain disciplines. There are some aspects of marketing that are measurable and quantitative but there are others that are not. Marketing is definitely one of those disciplines where it can be challenging to demonstrate success, so there is an art to mixing the qualitative and quantitative results. As a leader, though, setting clear targets, and managing to those on a sustained basis is a critical leadership trait.

      Ok, thank you for that. Let’s now jump to the primary focus of our interview. Most of our readers — in fact, most people — think they have a pretty good idea of what a C-Suite executive does. But in just a few words can you explain what a C-Level executive does that is different from the responsibilities of other leaders?

      This is my first C-Level role, but the biggest change I’ve experienced, and this might be Rocket Software specific, is that you spend a lot less time thinking about your function and more about the company as a whole. I’ve learned the following from Andy Youniss, Rocket’s CEO, which really transformed the way I thought about my CMO role. Each of us has three jobs in order of priority:

      1. We are a partner to the CEO. It’s our job to provide unsolicited feedback, ideas, and suggestions.
      2. Your team is the leadership team. That is your first team and your priority. You’re supposed to think as an enterprise leader first, not a functional leader.
      3. Your role as a functional leader. For me, my title is CMO, but that’s my third most important job.

      You really spend a lot less time thinking about your functional area and more time thinking from a business perspective across the entire enterprise. Your calendar and decisions should reflect that.

      What are the “myths” that you would like to dispel about being a CEO or executive? Can you explain what you mean?

      That we’re the smartest people in the room. I can assure you from personal experience that this is not the case. All of my direct reports are smarter and more knowledgeable than I am in their functions. I’ve learned so much from different people across the organization. We do not know the most about everything. In fact, we probably know the most about very few things that our team and subject matter experts do.

      The other is the we’re too busy for the people side of things. While our calendars might be packed, the single most important thing that we do as leaders, is develop people. You’re responsible for hiring and retaining people. As you move up the corporate ladder, you have more scope and responsibility from numbers and budgets, you do less and less work as a C-Level. You’re actually enabling others to do the work and eliminating the boundaries and the impediments to others being productive. At the end of the day, your job is resource management.

      What are the most common leadership mistakes you have seen C-Suite leaders make when they start leading a new team? What can be done to avoid those errors?

      The biggest mistake that new leaders make is feeling like they need to make an impact sooner than needed. They feel like they need to make changes to prove their worth or their value and oftentimes, they move too quickly. Many times, they haven’t done the proper due diligence by not taking the time to listen to employees, customers, and partners to get a balanced view of what’s truly going on, of how things operate in reality, not on some PowerPoint slide. This is something that a lot of people just miss. And, that feeling of, “I just got the big job and need to show my value” weighs on new leaders like a heavy burden. My advice: don’t fall into that trap. Set clear milestones; achieve some quick wins along the way.


      I’ve been at companies where, outside of a once a year annual review, there’s not a lot of strategic cross-functional time spent on people. Fortunately, Rocket Software does the exact opposite. We continuously do calibration exercises and we do talk about leadership and people on other teams, there’s really a whole process and time allocated to this. A friend of mine from one of the global IT services provider companies told me that once a month, their ELT would fly in from all over the world into the Frankfurt airport and spend two days on a weekend to only talk about their people. There was no business talk. No customer escalations. Just talk about people. This is how important people are to an organization. This is by far the most important resource at a company. You truly can’t spend enough time on people and talent management.

      Ok super. Here is the main question of our interview. What are your “5 Things I Wish Someone Told Me Before I Began Leading From the C-Suite”? Please share a story or an example for each.

      1.Spend at least 25% of your time outside of the walls (literal and figurative) of your company. Engage with industry peers, customers, partners. Don’t get myopic and have tunnel vision.

      2. Your people should be your top priority — and your calendar should reflect this fact. Developing talent, eliminating hurdles, and empowering your team is how you will make the greatest impact as a leader.

      3. You are an enterprise leader first, and a functional leader second. Think about the business overall, and not merely your functional area. Your CEO expects it, and your customers and shareholders/investors deserve it.

      4. A lot of basics stay the same. Don’t change who you are, your values or your principles. Treat people with respect. Results matter. Culture — how you got there — matters more.

      5. Don’t sell your soul to the job. You will regret it. Your family will regret it. And, it’s not sustainable or beneficial for your company either. Work hard, yes. Some long hours, yes. But don’t put yourself in a position where your health — physical and emotional — is compromised. In today’s COVID world, this is an incredibly important point.

      In your opinion, what are a few ways that executives can help to create a fantastic work culture? Can you share a story or an example?

      Two things come to mind. First, reward and publicly recognize individuals and teams for modeling the right behaviors and for positive outcomes. At my Quarterly All Hands meeting, I announce a handful of awards for both the marketing team and an individual outside of marketing for their partnership. These awards go a long way to boost morale.

      The second is the have fun. Yes, COVID has called for Zoom happy hours and such. But, regardless of these crazy 13 months, keeping work light at times, getting to know one-another on a human/personal level goes a long way in driving the right culture and in turn, business outcomes.


      It would be around public service. After living in Israel, I came to an appreciation for shared sacrifice and public service. Imagine if every high school graduate did 3 or 6 or 12 months of public service -volunteering at an elderly facility, cleaning up parks or teaching at a school. I believe such a program would enhance student’s readiness for and appreciation of college. It would also add material value to our society and would inject a sense of community and shared sacrifice that would benefit the country immeasurably.

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