Jay Leader, CIO of Rocket Software, discusses his interview strategy and transition to the job in 2014.

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Our interview with Jay Leader, who became SVP of IT & CIO of Rocket Software in 2014.

How did you first hear about the CIO opportunity at Rocket Software?

I heard about it through an executive recruiter. I was in transition at the time, and every opportunity I heard about came either through a contact I had or an executive recruiter. Most of the serious opportunities came through executive search firms.

What did Rocket Software find most attractive about your professional background?

I have worked in software companies before and most of my professional experience is at high tech companies. So it was a good industry match, but the most important element was the stage Rocket was in at the time. It had grown beyond its infrastructure and there were major gaps to fill gaps in security, compliance, and program management. They saw that I had already done exactly that in previous roles. They liked that I had lived this journey before.

What else was the company looking for in their new CIO?

Founders are particularly interested in cultural fit. Do your values align with ours? Will the way you go about doing things fit with the way we operate? Culture is the most important thing at founder-led companies, and it can’t be changed.

“We are not power driven. If you can go help in another area of the business, go do it. It won’t be an intrusion. In fact, it is invited and encouraged.”

What piqued your interest in the CIO opportunity at Rocket Software?

The real driver was the ability to be impactful not just in IT, but in other places at Rocket. I could tell right away that the culture was one of collaboration and openness. We are not power driven. If you can go help in another area of the business, go do it. It won’t be an intrusion. In fact, it is invited and encouraged.

As an example, I am the executive sponsor for customer experience at Rocket. I am the CIO, but I also have strong influence over the entire customer lifecycle – initial awareness, sales, support. Everything.

Besides your resume, was there any professional branding that helped position you for the role?

There are a bunch of artifacts out there if you Google me. But I think that most of it was driven by where I had been and the kinds of companies I had worked in. We each have a brand. Mine is high technology environments where a very high value, and high expectations, are placed on technology.

No one should underestimate the incredible power of LinkedIn, and the importance of understanding how to use it. I had a good friend who is very fluent with LinkedIn help me tune my profile so that I would show up for all CIO searches in Boston. In retrospect, I don’t think I interviewed for a single opportunity where, through LinkedIn, I did not find a way to connect with someone in that company. It was instrumental in getting this job because of the level of confidence it instilled.

How did you prepare for your interviews?

I prepared my pitch. I internalized the key points I wanted to get across after researching the company: this is who I am as a leader, my strengths and qualifications, and the points that showed my affinity with the company. Several times in my mind, I went over a concise explanation of how my background was a fit the company, and the most relevant things I wanted to highlight.

Were there any surprises during the interview process?

Part of the process included a phone interview with a private equity partner. I hadn’t been part of that type of interview before. He was more focused on qualifications rather than culture and soft skills. Afterwards I felt like I had been in a prize fight, but he was just doing his job. When we met the second time, it was face to face and it was very different. I had time to reflect and prepare and, in person, there is the benefit of body language and eye contact.

One thing that blew me away was people’s willingness to help me. During this job search, people went to extraordinary lengths to help me out. It so far exceeded my expectations that I was shocked. I talked to one guy I hadn’t spoken with in 20 years and he was so enthusiastic and helpful. People genuinely want to help.

Who do you report to?

The founder and CEO.

How did you prepare to start your new role?

I spoke with one of the two directors I was inheriting. I started drafting a 100 day plan, but it wasn’t focused on project objectives. I decided I would start with an assessment to identify the major gaps, my stakeholders and their business priorities. It was a good thing because, when I arrived, my boss asked for a 100 day plan.

From day one, what are some of the concrete steps you took to learn the business and build relationships across the enterprise?

Learning the business is evolutionary. We are a software business. I have been here a year but there are things I haven’t learned yet about Rocket. But I did take steps to learn about the key stakeholders and what was important to them. At the end of the day, that drives what we do here.

Did you find anything that was 'on fire' and needed to be dealt with right away?

We had some things in flight that I stopped because I thought they would not succeed. The management team had a few misconceptions about the effectiveness of some of the things we were using, so there was some level setting that had to be done early on. It wasn’t the software that was the issue, but processes and people.

What organizational changes did you implement?

I was hired to fill critical gaps which meant standing up new functions in IT that Rocket had never had before: program management, enterprise architecture, security and compliance capabilities. Also, the leaders of the applications group had left the company, and the positions were kept open so that the next CIO could hire them. So that group has been rebuilt. The infrastructure group was, and is very strong, and didn’t need any fixing.

Have you made any significant changes in the technology?

No, I didn’t have to rip anything out. The tools are solid. It is how we operate them, the processes. That is where the maturation and scalability has to happen.

What does ‘digital transformation’ mean at Rocket Software?

I would have to say ‘customer intimacy.’ It is all about our customers, what they think, want they need, how we interact with them, how we drive a most productive customer experience. Much of our business is in legacy environments, so it’s important that we keep our existing customers. We need to be a key strategic supplier. Outside IBM, we know more than anyone else about mainframes. There is no reason we cannot be a host and a gathering point for mainframe people.

What advice would you offer to someone about to embark on a CIO job search?

What I didn’t understand is that networking is most valuable if you do it before you start looking for a job. A lot of people only network when there is a reason, like when you’re out of work. It’s hard to start from zero. You have to nurture your network in good times and bad.

About Jay Leader

CIO_Rocket_Software_Jay_Leader_125Jay D. Leader is Senior Vice President of IT and Chief Information Officer at Rocket Software. Prior to Rocket he was VP & CIO at Rapid7, a developer of Vulnerability Management and Penetration Testing software and tools, and SVP and CIO at iRobot Corporation, the leader in consumer, industrial and government robotic products and technologies.

Leader is the former Chairman of the Boston Society for Information Management CIO Roundtable, and was named the 2010 Massachusetts CIO of the Year by the Massachusetts Technology Leadership Council. He was also named one of Computerworld’s 2011 Premier 100 Leaders in IT. Mr. Leader is a graduate of Clark University, Worcester, MA, where he earned a BA in International Relations and an MBA.

About Rocket Software

Rocket Software is a global software development firm that builds enterprise products and delivers enterprise solutions in the following segments: Business Information and Analytics; Storage, Networks, and Compliance; Application Development, Integration, and Modernization; and Database Servers and Tools. The company is headquartered in Waltham, Massachusetts, USA.

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