CIO Spotlight: Brian Winters, ECI Software Solutions

Name: Brian Winters

Company: ECI Software Solutions

Job title: CIO

Date started current role: May 2019

Location: Dallas/Fort Worth Area

As Chief Information Officer, Brian Winters ensures ECI executes on its promises. He leads the delivery of ECI’s cloud-based SaaS solutions, the constant evolution of the company’s cybersecurity stance and the management of corporate information technology operations. What drives Winters? His focus on the success of ECI’s customers internally and, most importantly, externally. Winters is a seasoned technology executive with a passion for customer delivery. Along with his customer-first mentality, he brings more than 15 years of leadership experience where he has held senior technology positions at companies including Solera Holdings, Top Image Systems, and eGistics. Winters specialises in building and managing the infrastructure and operations necessary to deliver business-critical services securely via the cloud, and in positioning PE companies to maximise value.

What was your first job? I grew up on farm in central Kentucky so my very first job was working on the farm, taking care of the cattle and tending the fields. My first paying job was working at Long John Silver’s when I was 14 – it was the only place that would hire me at that age. My first “real” job was when I started my own business at 20 – back when I thought I knew everything and running a business was easy.

Did you always want to work in IT? No. I thought I wanted to be a history teacher. I developed a love for computers in high school because of video games, and that turned into a career. At that age, I didn’t even know IT was a thing that people did for a living, I just knew I wanted to spend as much time working on and with computers as possible. 

What was your education? Do you hold any certifications? What are they? I have a Bachelor’s in computer information systems and a CISSP certification from ISC2. I’ve held a host of other certifications throughout my career but let them expire as they became irrelevant.

Explain your career path. Did you take any detours? If so, discuss. I took out an SBA loan at the age of 21 and started my own Wireless ISP. I thought I was going to be the next Bill Gates, but after five years competing against the cable and phone companies, I was offered a job at a start-up by one of my customers, so I sold the business to a competitor and started my formal IT career. From there I took a pretty normal run through the corporate ladder from individual contributor to manager, a couple of director and VP jobs and then my first CIO position. Though it didn’t turn out exactly how I’d envisioned, I do think that owning my own business (which I call the school of hard knocks) at such an early age did help me stand out among my peers and accelerated my opportunities to advance in IT quickly.

What business or technology initiatives will be most significant in driving IT investments in your organisation in the coming year? ECI is a cloud service provider, and our customers trust us with their critical business data, so we spend a lot of our time focusing on security enhancements. We’re continuing to move towards a zero-trust model which is driving a lot of our activity now, and into 2022. We are focused on enhancements like expanding our MFA capabilities and continuing to reduce network scope through micro-segmentation.

What are the CEO's top priorities for you in the coming year? How do you plan to support the business with IT? We are highly acquisitive, so we put a lot of thought, time and energy into buying and integrating companies, especially on the technology and security side. We do a good job at this now, but we continue to drive innovation in this area to support the business’s desire to ramp up M&A activity.

Does the conventional CIO role include responsibilities it should not hold? Should the role have additional responsibilities it does not currently include? I think the CIO role is constantly evolving and it varies a lot from company to company. I’d agree that in some companies, the CIO role has scope that doesn’t make sense – which is usually the result of leftover operational scope that doesn’t fit neatly in other areas or that no one else wants to manage. It is unfortunate because it can really distract from the important priorities. As agile and lean have taken over R&D and product teams, and with efforts like DevOps that blur the traditional lines, I think CIO’s must constantly re-define their role in their companies or risk becoming the office of “no” and failing to deliver business value. 

Are you leading a digital transformation? If so, does it emphasise customer experience and revenue growth or operational efficiency? If both, how do you balance the two? We’ve been on a digital transformation journey for several years. If you define digital transformation as “technology being integrated into every facet of the business” then I would argue we are largely there and working on continuous improvement. My approach is to focus on both customer experience and operational efficiency – I find that they very often drive you to the same outcome if you are being transparent and asking the right questions. Usually if those two objectives are at odds with one another it’s because we haven’t properly defined the desired business outcome. Not every service needs five-nines of uptime – and a lot of the operational efficiency and cost reduction we do now revolves around properly understanding the costs for that extra nine and making informed, data-driven decisions on where to invest.

Describe the maturity of your digital business. For example, do you have KPIs to quantify the value of IT? I would say, like any company, we have areas of focus where we have well-developed KPI’s that have been iterated many times and are well understood. On the other hand, we also have areas where KPIs are rudimentary and still being improved and refined. 

What does good culture fit look like in your organisation? How do you cultivate it? ECI has a really strong culture that is focused on our mission of enabling small to medium-sized businesses to run their businesses more efficiently and effectively. I think that mission attracts a certain type of person. We try to avoid tech extremists who feel like there is only one “right” way to build something and, instead, try to focus in on people who want to be part of building something meaningful and who understand that diversity of perspective is important and that sometimes the “perfect” solution isn’t the “right” solution.

What roles or skills are you finding (or anticipate to be) the most difficult to fill? Security roles are the hardest to find qualified people for, and I believe that trend will continue. The CrowdStrike’s and other MSP’s of the world are snatching up all of that talent at crazy “unicorn” salary ranges and in the next five years, I think it will become even more difficult to hire these roles. As a result, many companies, especially smaller companies, will have to migrate largely to an MSP model. DevOps and SRE roles are also hard to find for the same reasons.

What's the best career advice you ever received? What you do in moderation, your team will do in excess – both good and bad. One of my mentors imparted that wisdom one day when I did something silly like came to work wearing shorts and it has stuck in my head ever since. It is 100% true and I think about it constantly.

Do you have a succession plan? If so, discuss the importance of and challenges with training up high-performing staff. Yes, we do.  It’s not as robust as say a company like Toyota where it’s a very formal process, but we do have a training and development office with some of the most amazing people I’ve ever worked with. We have several formal programs for high-performing staff including mentoring and training programs. I think the biggest challenge in succession planning is that the supply and demand of good IT resources has tilted to the point that we’ve moved into an era where people can and do get significant salary increases by moving to a new company every 2-3 years and most companies are still hesitant to match that opportunity for existing employees. So, when an employee is faced with a headhunter cold calling them for an opportunity right now with a 30% pay raise or waiting for someone above them to leave the company to move up with a smaller pay raise, it’s an easy choice.

What advice would you give to aspiring IT leaders? Don’t waste your time working in companies where IT is not seen as a critical part of the business. If you are interviewing, ask the interviewer if the CIO is able to drive change in the business or if they feel like their hands are tied. If the latter, find another opportunity – you aren’t going to learn and grow in that environment and long-term, it will not help build your career.   

What has been your greatest career achievement? I suppose the answer here should be one of the acquisitions I’ve been a part of, the cool cloud delivery capabilities we’ve built or a digital transformation story, but I personally get a lot of joy from the mentoring and development side of the job and I think my greatest career achievement would be the great friendships I’ve developed over the years by helping the amazing people I work with get where they want to go. 

Looking back with 20:20 hindsight, what would you have done differently? I spent my early career chasing salary dollars vs. chasing opportunities that I really felt would help me grow or gain new experience. I would do that differently.