CTO Sessions: Debra Danielson, Digital Guardian

How do you align your technology use to meet business goals? “Using metrics. If you can’t measure it, you can’t change it.”

Digital Guardian

Name: Debra Danielson

Company: Digital Guardian

Job title: CTO and SVP Engineering

Date started current role: April 2019

Location: Digital Nomad

Debra Danielson is CTO and SVP, Engineering at Digital Guardian, where she provides the technical vision and strategic direction for product innovation while overseeing the engineering function for the DG Data Protection Platform, including product development, quality assurance and sustaining engineering. Prior to DG, Danielson was at CA Technologies and has held technical, strategic, operational, and managerial roles over her 30+ year career throughout the company. Additionally, she is a member of the board of directors of Rock Solid Technologies and has advised CEOs, CTOs and boards for more than 10 years on the business of technology.

What was your first job? There are many ways to answer that question. My first paid (non-babysitting job) was at the Dairy Inn, serving ice cream. My first job in technology was a summer internship at the Princeton Plasma Physics Lab, where I had my very first system crash due to a bug in my code!  I tried my hand at independent consulting right after college graduation and working under contract to Panasonic, created a software interface to a prototype Panasonic Optical Disc Recorder for the Consumer Electronics Show in 1983.  (Written in Forth!) My first full-time permanent job in technology was with Applied Data Research in QA.

Did you always want to work in IT? Actually, I tried hard *not* to work in IT.  My father was a professor of Astrophysics at Princeton University, and it was a very natural field for the daughter of a (effectively) mathematician to go into tech. I was somewhat (well maybe more than somewhat) rebellious and wanted to be a fighter jet pilot. Unfortunately, women weren’t allowed to fly in combat when I graduated from high school, so the military option was out. I started in Aerospace and mechanical engineering, but sadly for me at the time (but ultimately happily for the today me), I wasn’t good at it, but I was really good at coding. For the record, I did eventually get my pilot’s license.

What was your education? Do you hold any certifications? What are they? Ha! Well, I referred a bit above to my somewhat checkered path in college. I was a bit of a wild child. I picked courses based on what I was interested in at the time – rather than focusing on a degree – and I wasn’t particularly good at seeking or accepting advice. When I finally had to talk to an advisor about graduating, I found that I was going to end up with a degree in Economics and Applied Mathematics. 

I suppose it took me a while to 'grow up' and become a working professional.

Explain your career path. Did you take any detours? If so, discuss. I have a fairly non traditional career path – particularly given that I have only worked for 3 companies across my entire career. For 15 years I wrote product code, architected product code, and managed product development.  I earned the reputation of the person to take a new project to – particularly if it was new technology. That meant I was always working on the new OS, on the new tech, with the new hardware. Many of those projects failed, and virtually all of the ones that failed – failed because of market timing and user experience. A massive lesson that has stayed with me through my career. Somewhere around here in my career, I was made a distinguished engineer and elected president of the Council for Technical Excellence, with responsibility for coalescing the top 2% of deep thinkers, pre-eminent domain experts and thought leaders across multiple business units into group which could be leveraged by executive leadership for technical guidance in the business and which could foster innovation.

I was then offered a position in the Corporate Development and Strategy organisation leading to a 10-year stint of my dream job (SVP, M&A Strategy and Distinguished Engineer). I had the opportunity to meet and learn about the technology, products, engineering methodologies and cultures of many hundreds of start-ups (and not so start-ups), and to go through the acquisition process with many. It was like getting a PhD in what makes a software company great and what makes them fail.   

That landed me at Digital Guardian. The newly minted CEO knew me from the CA days (indeed he came into the company via an acquisition, so he got to know me well even before joining); knew that I was on the market and offered me the CTO role.

What type of CTO are you? I’m the kind that speaks the language of business and understands that technology is the business, and the business is the technology.    

While responsible for tech diligence at CA, I realised that the engineers responsible for our prior acquisitions had fallen into a trap that’s typical for techies. They’d evaluated the potential acquisition targets and provided technical assessments to the business leaders without a financial or business context. Those thoughtful tech evaluations were effectively ignored, the acquisitions went ahead, and the business cases weren’t achieved. The techies just couldn’t believe it! For the next acquisition, I created a framework to translate individual technical warts into a specific impact on the business case. Inefficient architecture? Increase the COGS and the cost to maintain. No internationalisation? Delay any forecast for non-English speaking geographies and increase the development costs during integration.  

Which emerging technology are you most excited about the prospect of? Fully Autonomous vehicles. My mum is 86 years old, and she just bought her first (somewhat) autonomous vehicle.    

She and I previously discussed how long she was going to be able to continue to drive (she’s still a great driver).  But there will be a point where she becomes less comfortable driving in the dark or on the highway, and her reaction times will slow. Her world will shrink dramatically if she can no longer drive. By buying and gaining confidence in the car as navigator and driver, I expect her to non-trivially lengthen the time that she can live independently and to keep her world as big as possible.    

I also believe that autonomous vehicles will drive a different ownership and user model, particularly for the lower end of the economic spectrum, and that in turn will deliver mobility to many that do not have it today. The ability to have safe, convenient and economical transportation regardless of your physical or mental condition can be a potent opportunity equaliser.

Are there any technologies which you think are overhyped? Why? I have to insert the word “now” when I consider that question. Because every technology is hyped at some point in its lifecycle – the big question is whether an overhyped technology can survive the disillusionment that follows to find a place in the world of productive tech.  I did an evaluation of the impact of machine learning and AI on the start-up ecosystem from 1999 to 2019 which showed the waves of investment across the areas where we take capability for granted today. It was a fascinating analysis of how a technology transformation takes place, and it only very rarely is a straight line.  

That said, I think we’re at a very dangerous point in our technology evolution. Our technological capabilities are growing in leaps and bounds, yet we haven’t fully developed technical, legal and ethical frameworks to ensure that we can identify, curb and punish the criminal and/or deeply unethical uses of that technology. At the same time, our evaluation frameworks are being undermined: Where can you get information you trust? How do you know you can believe it? I recently watched “The Poison Squad” and was shocked at the process that took place while the country transformed from an agrarian to manufacturing base – how ignorance and unscrupulousness intersected to form a frighteningly unsafe food chain.  It took more than 50 years to achieve the certainty that we enjoy today in the United States that our food is safe. I hope we don’t have 50 years to go before we know that our data is consumable without disastrous side effects.

What is one unique initiative that you’ve employed over the last 12 months that you’re really proud of? I’ve been working on creating a culture in engineering whereby people know how their work contributes to the success of the organisation – and where they have an appropriate amount of autonomy in getting there. My philosophy is to create an engineering organisation made up of adult professionals. I treat them as adults and as professionals and they behave as adults and professionals. Our employee satisfaction in engineering has almost doubled in 18 months – as measured by the number of employees willing to recommend working at DG to their friends and professional acquaintances.     

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 delivering DLP from the cloud for almost 5 years, so I’m not sure I can claim the digital transformation there, but I have been driving a modernisation of the engineering processes and pipeline and establishing a data-driven engineering process. I am focused on managing the lifecycle of foundational technologies – the perfect modern solution of 7 years ago can easily become “legacy” if not managed. New technologies, new tools, new paradigms emerge all the time. The balance between jumping on the bleeding edge whenever it arrives or delaying until one day you wake to find your tech stack outdated must be actively managed.  We manage the balance by being explicit about the levels of investment in each and tracking it. I’d like to say that there’s a magic formula for that balance, but it’s both art and math.

What is the biggest issue that you’re helping customers with at the moment? The pandemic has increased the number of companies with full or hybrid WFH workforces. It happened to us at Digital Guardian, as we moved fully to WFH a full year ago. That transformation puts a renewed emphasis on providing effective and coordinated data protection on the endpoints that employees use every day.

Many customers tell us that even after the pandemic subsides, they plan to maintain a hybrid workforce. So, we are focused on helping our customers update their security strategy to encompass the realities of permanent work-from-anywhere (WFA) employees. For example, WFA employees will continue to leverage collaboration for effectiveness but this model of collaboration can increase the risks of data egress. We recently launched new capabilities that extend our endpoint DLP across prevalent collaboration software like Microsoft Teams, Slack, Zoom, and Skype.

How do you align your technology use to meet business goals? Using metrics. If you can’t measure it, you can’t change it.    

Do you have any trouble matching product/service strategy with tech strategy? Not trouble. This is the fun part of the CTO role. It’s a puzzle that needs to be put together by looking at the potential tech trajectories and seeing which one best supports the product strategy. Ultimately, architecture and technology are the infrastructure which delivers value to the customer. If you ever get that backwards, only supreme luck can rescue you from disaster.

What makes an effective tech strategy? Results. At the end of the day, the success of the tech strategy is measured by the cost-effective delivery of a compelling value proposition to the customer.  

What predictions do you have for the role of the CTO in the future? Increasingly technology is becoming the business, and the business is delivering technology. For two years, I’ve been on the board of Rock Solid Technologies, principally framing technology issues in business terms. More and more companies are looking for technologists for their boards, reflecting the importance of technology in governance of the business. The CTO isn’t just the dude who knows about tech, he or she is a business leader with a specialised skill that’s critically important to running the business.

What has been your greatest career achievement? While it’s hard to pinpoint one, achieving the Distinguished Engineer (DE) recognition is one that stands out as far as a personal career achievement (versus an impact on an organisation). Distinguished engineer is the highest level of technical contributor at CA. It was executive level, carrying an SVP band and authority. I was one of the first 7 people in CA to be given the Distinguished Engineer label and the first woman. The Distinguished Engineer was not a job, but a recognition, and it followed wherever you went in CA. I was President of CA’s Council for Technical Excellence and Distinguished Engineer, then SVP, M&A Strategy and Distinguished Engineer. To put it into perspective, CA had about 5000 engineers. The DE isn’t just about technical competence, but it required someone who understood the business implications of technology, and was recognised inside and outside of CA.    

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