The Path to CIO: The Building Blocks of a CIO


“When I grow up, I want to be a CIO”, said no child...ever! Fireman, policeman, doctor, just about anything...but not CIO! Isaac Sacolick wanted to build...bridges, buildings, trains. His love for erector sets eventually led him to Radio Shack and engineering of a different kind. By the age of 12, he was on a path, doubtful he knew it at the time, but he was on...The Path to CIO.

I started following Isaac after he was named to the Top 100 Most Social CIOs by Vala Afshar (a list to which I aspired, but never quite made it...come on Vala, give a brother a break!). As I read more of Isaac’s posts (he blogs at Social, Agile and Transformation on topics for CIO), I found myself agreeing with just about every concept he shared. I was thrilled when he agreed to be a part of this series.

Jeff: Isaac, thank you again for taking the time to be interviewed for this series. You credit your father for your interest and passion in computers. How did he influence you and start your down this path?

Isaac: I grew up in the Atari 2600, Intellivision generation and with some of the older tv console game machines. But my dad was an engineer and saw the games as expensive and of limited educational value. He bought me a Commodore Vic 20 and later a Commodore 64 to learn programming in Basic and other computing basics. I learned how to program and how computing systems functions, but what grabbed my attention the most was dialing into various Bulletin Board Services (BBS). I eventually got my hands on some software and opened a couple of my own including a BBS for dungeons and dragons playing and another for Commodore enthusiasts. One had a rudimentary dating site that a handful of people paid for access. I was 12.

Jeff: So, at the age of 12 you set the foundation for THAT truly is a different path to CIO! I can hear your acoustic coupler modem from here! Seriously, I find it fascinating, this is the third profile in this series and the common theme thus far is...Commodore 64. A zillion years ago, I had one as well. I wanted to learn machine language but couldn’t afford an Assembler, so I wrote one...but I was in my 20’s, not 12!

Many people who spend a career in IT are eventually faced with a ceiling of sorts. At some point they are faced with the decision to “stay technical” or move into managerial roles. Was this a conscious decision on your part?

Isaac: After grad school, I was hired as an engineer to join a team of five working on commercial genetic analysis software. I stayed almost two years developing software that enabled comparing genetic samples. It was a great experience, but when the company went up for sale, I went looking for new opportunities.

I made a decision that I liked working for startups and that the internet had huge growth potential, so I joined a startup that was helping newspapers build websites to search classified ads online. I was the second technologist hired and offered the role of Director of Software Development.

Being in a startup in the early days of the internet, I was able to be technical, managerial, and develop business skills. One day I might be configuring servers, the next day designing new search algorithms, and the last day working with product management on the next set of features.

Jeff: As you moved more into management, what were the influences on the management style you adopted?

Isaac: I had many influences. Hands on managers that knew how to do the work, improve process and organize teams. Marketing leaders that knew how to collaborate with engineers to get optimal solutions. Business leaders that knew how to handle difficult transitions and transformations when there was strong conflicting viewpoints. CIOs that developed enterprise solutions and developed practices and governance so that business unit teams elected to adopt them.

Jeff: Was there a moment in your career when you knew you wanted to be a CIO?

Isaac: When the founding CTO, Ian Lintault decided to move on a few years after I joined, I knew I wanted the role. It was a big step because we had just closed a strategic round of funding and there were a lot of questions from newspaper executives about how the internet worked, how we would scale, how much funding was required, and ultimately how we would develop digital products that complimented their print offering.


I knew few other CTOs at the time so he was and remains one of my early influencers.

After another round of startups, I decided to try bringing startup speed, agility, innovation, and digital capabilities to the enterprise. I went looking for enterprises looking to transform and joined McGraw Hill as a business unit CIO first at BusinessWeek and then with McGraw Hill Construction (now Dodge Data and Analytics). There were a good number of people who influenced me at McGraw Hill on being a CIO including Keith Fox who was BusinessWeek and Construction's President, Linda Brennan who who VP of Marketing and Operations at these businesses, and Adriaan Bouten who was the CIO of the Information and Media sector.

Jeff: Thinking back over your career, what key learnings or discoveries about yourself did you uncover and how did you use those to propel yourself into a leadership role?

Isaac: I learned to trust my instincts. There is no definitive guide on how to partner with business leaders and run efficient technology teams that can execute an agenda of transformation and product innovation. I stuck with several basic principles and have evolved them over time and experiences:

        • Build an agile practice.
        • Challenge business and technology assumptions and provide new solutions
        • Develop a data driven culture and technical capability
        • Enable experimentation to get more innovation.
        • Develop transparency around project portfolios, investments, status, and KPIs
        • Take steps to learn client needs, workflows, and opportunities
        • Collaborate and share what you’re thinking.

Jeff: Those are great principles. Building blocks, if you will. Sounds like you still like to build! What advice would you have for someone considering a career goal of CIO? What new skills should they hone to be a CIO in 2020 and beyond?

Isaac: A CIO needs to lead through a variety of experiences in order to be successful, so those aspiring to the role need to make sure they are always learning, taking on a variety of new challenging responsibilities, and demonstrating wins. In doing so, aspiring CIOs have to develop a playbook of how they will lead organizations, manage people, and enable transformation. For me I applied practices like agile development, self-service BI programs, and innovation practices to be successful in a number of CIO positions.

I firmly believe that CIOs need to have a technical foundation and have the ability to architect and communicate solutions. They need to be able to review platforms and make technology investments that can be applied to multiple business needs. They then have to be a consultant to business stakeholders, listen to their needs, consult with them on options but most importantly, sell them on a solution. This is essentially how CIO can “learn the business”.

But learning and partnering isn’t sufficient because today’s CIOs are expected to lead transformational efforts. To do this successfully, it takes a whole new set of skills to master starting with understanding industry dynamics, customer needs, and competitive factors. CIOs then need to be able to challenge the existing operating model and propose new ways to deliver solutions that customers value.

Jeff: Isaac, I noticed you mentioned marketing several times in our conversation. I find that interesting, in so many cases IT and marketing are almost adversarial. You’ve broken those walls. Case in point, you have really embraced social media. In fact, you and I actually met in the Twittersphere. I have really enjoyed reading your blog and have implemented some of your ideas in my own shops, so first of all, thank you for sharing your insights! As a final question, how did you come to embrace social media in general and blogging specifically?

Isaac: I founded a travel social networking company and then developed a link sharing product at BusinessWeek. Both products required a strong understanding of how to develop social networks by providing value to contributors, participants and consumers. To understand the dynamic, I decided to embrace social networking first by creating the blog Social, Agile, and Transformation and then by being an active contributor as @nyike on Twitter and other networks.

I use the blog to share knowledge and insights on agile, business intelligence, digital transformation and other topics. I have almost 300 posts over ten years of blogging, and have also contributed to other websites and publications. On Twitter, I share what I am reading and participate in various conversations. I’ve met some very special people through these interactions and it’s a great way for CIOs to share their knowledge.

The series, “The Path CIO” explores the careers of CIOs from around the globe in a variety of industries. Each month we will feature the story of their journeys and answer the question, “How DID you become a CIO?” (If you have held the role of CIO and are interested in telling your story, please reach out to me via the links below!)

Jeffrey Ton is the Executive Vice President of Product and Service Development for Bluelock. He is responsible for driving the company’s product strategy and service vision and strategy. Jeff focuses on the evolving IT landscape and the changing needs of our customers, together with the Bluelock team, ensures our products and services meet our client's needs and drives value in their organizations now and in the future


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Published on Categories IT LeadershipTags , , ,
Jeff Ton

About Jeff Ton

Throughout his career in business, Jeffrey Ton has developed and fine tuned his leadership skills to become a business focused leader who drives results. Extending the role of the CIO to encompass a strategic view of the business, he identifies innovative approaches to achieve the business objectives by leveraging technology where and when appropriate. Adept at building and leading teams, both in-line and cross-organizational, he has been a catalyst for change across the businesses he has served. Ton has industry expertise in information technology, non-profits, commercial real estate development, manufacturing, warehousing and distribution, supply chain, green/clean technologies, finance, insurance and consulting. Expertise: • Strategic Planning – Business & Technology • Organization & Management Reengineering • Merger & Acquisition Integration • Divestiture Decoupling • Business & IT Alignment • Enterprise Architecture Strategy • C-level Relationships • International Staff Management & Acquisition • Global Enterprise Implementations • Fiscal Management • Governance & Risk Management • Business Process Optimization • Vendor Relationship Management • Outsourcing(Offshore/Near-shore) & In-sourcing • Technology Portfolio Management • Regulatory and Compliance Management • P&L Management Specialties: Architecture, infrastructure, applications, application development, telecom, e-Business strategy, web development, knowledge management, integration, EDI, SAP, business intelligence, outsourcing, insourcing, contract negotiation, commercial real estate development, manufacturing, warehousing and distribution, supply chain, green/clean technologies, finance, insurance and consulting, keynote speaker on leadership, green and other topics, LEED AP BD+C. Read his blog on, Intel's IT Peer Network and LinkedIn.