Evolving Syncsort: CEO Q&A with Josh Rogers (Part 1)

Josh Rogers is CEO of Syncsort, a B2B software company that helps businesses organize their data. Since taking the helm in 2016, this first-timer has led three years of major growth, both organic and via nine acquisitions that have quadrupled Syncsort’s size. He has quadrupled revenue, increased their customer base to 7,000+ (including 84 of the Fortune 100), and expanded their solution set.

No stranger to evolution, the 50-year-old company is looking steadfastly towards the future of data under Josh’s leadership: They are exploring how they can support blockchain, AI, and machine learning.

Here’s how Josh got to be CEO after a long career at Syncsort and how he leads.

Syncsort CEO Josh Rogers

Syncsort CEO Josh Rogers

When you were starting out in your career, did you aspire to be a CEO? Either way, how did you end up becoming one?

I went to Davidson College, which is a small liberal arts institution. I was an economics major and directionally found the business world interesting. Based on classmates ahead of me and my recruiting options, I pursued a role in finance. I ended up getting involved in M&A for a regional boutique bank and then at Wells Fargo and Bank of America. These were great opportunities to learn about business.

Was there any point where you thought the CEO role might be interesting? 

When I worked at a private equity firm (Bank of America Capital Investors), I had the opportunity to attend board meetings and got excited about the operating side of business. I heard the CEOs of our portfolio companies discuss their various strategies. It seemed like an exciting role they were playing. It was challenging but their success was gratifying. That was something I wanted to be a part of in my career.


You’ve had a long career at Syncsort, starting in sales. What was it like to take your first real multi-functional role with the President title? 

It was a great experience, because I could steer the ship faster than in my VP of sales role. I originally joined Syncsort as a regional sales leader for the Americas and quickly became VP of sales. It was an exciting time for me. In my executive sales role I always had a bigger influence on the company than just my function. That was partly because I was a very curious salesperson/leader. I wanted to know why customers were making decisions. Why did we lose a deal, for example?

In general, I studied industry trends and knew there was a bigger opportunity for Syncsort in the big data space. I partnered with the heads of product, technology, and marketing to craft what that strategy could look like. When I proposed that strategy to the board, they liked it and asked me to implement it as President. I became responsible for all of the business line functions, including development, support, marketing, business development, sales, and more. You can make decisions a bit more quickly when you have a single leader in charge of the entire strategy.

In my experience, sales leaders have had strong ideas about what I should be doing differently as CEO. Today, is there anything you told your CEO as a sales leader that you now realize was not correct?

That’s a great question. We were always a pretty collaborative leadership team. That continued as I took over the President role. I did not get it exactly right out of the gate. One difference when I became President was a focus on data. For example, when we lost a deal we analyzed why and learned from that. It wasn’t about which function was doing things right or wrong, but what is the data showing us? Then we would adjust the strategy to win the next deal. This resulted in the Big Iron to Big Data positioning of Syncsort today.

Is there one area that you’ve found more challenging as CEO?

I would say that each of the functional disciplines has been a great learning opportunity for me. All are complicated in their own right, so I’m not sure I could hold up one as being the most challenging. Being a liberal arts graduate, you learn how to learn, so that’s what I’ve tried to focus on as CEO. Since I came up through sales, probably my biggest challenge is that I spend more time on the other functions.

Are there areas you would have studied if you’d known you would become a CEO?

Deeper technical expertise would have been useful. In our development process, it would make it easier understand what is and is not possible. Although this has not been a major hindrance for me.

What would people say has changed with you as CEO of Syncsort compared to your predecessor?

That is a dangerous question, considering my predecessor was Lonne Jaffe who is currently on our board of directors! In many ways I am executing a strategy that Lonne put in place. It’s a dual strategy, both organic and inorganic. We have evolved that pretty significantly. The biggest change frankly is that we’ve figured out with a high degree of conviction that the strategy is working. We’ve been able to put significant resources towards it and figured out how to scale those components to execute quickly against the strategy. As a result, we have quadrupled Syncsort’s revenue and employees since I became CEO. We’ve been able to anticipate where the market is going and figure out where Syncsort can help bridge that gap for our customers, using their existing solutions as a base. We’ve also focused the sales force on targeted sales plays where Syncsort has competitive differentiation.

How would you categorize how you spend your time? Internal vs. external facing?

I recently did an analysis on where I’m spending my time: It’s about 40 percent external and 60 percent internal. That is about right. There are times where I’d like to be higher on external. In Q2 and Q3 I am about 50 percent external. In Q4 and Q1 where we are planning for the year, I’m about 60 percent internal. Generally I’d like to run even, but it runs a bit more internal.

On strategy vs. tactical issues, I spend about 25 to 30 percent of my time on strategic issues. I wish it was closer to 40 percent. We made several tactical moves last year to propel our growth, including several transformational acquisitions. That’s why I spent more time on tactical to ensure those larger acquisitions were seamlessly integrated. In the future, hopefully I can shift my time to more long-term strategic planning.

Stay tuned for Part 2 of my discussion with Josh next week!


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