CTO Sessions: Kirsten Wolberg, DocuSign

Are there any technologies which you think are overhyped? "I think AI and Machine Learning are over hyped in a big way..."

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What was your first job? I had a paper route. I grew up in Anchorage Alaska and was just 7 years old when I got a job delivering the morning newspaper, the Anchorage Daily News.

Did you always want to work in IT? No. I started my career in product management in the financial services industry for my first "real" job. At that time I never really considered a career in technology and didn't transition into tech until mid-career. I was working at Charles Schwab (a US based online brokerage), and had an opportunity to join the IT division. I looked at my resume and realised it was the only area I where I didn't have direct experience. I'd been in marketing, strategy, finance and operations but not IT, so I took the job. I ended up loving it, and have not left the technology field since.

What was your education? Do you hold any certifications? What are they? My undergraduate degree is from the University of Southern California. My major was Business Administration and my concentration was Finance. I also have an MBA from Kellogg, in Chicago and my concentration was finance, information technology and international business.

When working in banking and brokerage I was a Certified Cash Manager, and held a Series 7 brokerage licence. Both have lapsed as I no longer work in financial services.

Explain your career path. Did you take any detours? If so, discuss. I took a lot of detours… Right out of college, I took a role in product management for a commercial bank, then a role in operations for a savings and loan bank. I then moved into consulting in the financial services industries. I stayed in consulting for 7 years working for two different firms.

Then, in 1997, a group of us from the firm left to be founders of a start-up in the Bay area. At that time everyone was leaving great, stable jobs to join start-ups. Our company, innoVentry, deployed self-service machines, like an ATM machine, convenience stores and grocery stores. Our machines were focused on serving consumers without bank accounts, and provided check cashing and money order services. 

It was a great idea that had a lot of traction, unfortunately the timing was bad. We ran into the crash of the ".com bubble" and the company went out of business.

For my next role, I joined Charles Schwab. Initially, I was an internal consultant in product, before moving into IT. I left Schwab to become the CIO at Salesforce. From Salesforce I had an opportunity to move back into financial services and was at PayPal for 5 years where I COO within the technology organisation.

When eBay and PayPal split into two companies, I led the separation transaction on the PayPal side. After leaving PayPal, my plan was to focus on my public company boards and on advisory roles, but then Dan Springer, CEO of DocuSign called. Dan and I had been on Year Up, a non-profit board together for about 10 years. He lured me to interview for this great opportunity at DocuSign - I loved what I learned about the company and the product so I left my self-described "wave 1 retirement" to come back into an operating role and work at DocuSign!

What type of CTO are you? When you read about CTO's it seems they fall into four different categories. One is the focused on the infrastructure and operations side of tech, then there are those CTOs that are deeply technical and visionaries from a technical perspective. The third are the customer champions and they really lead from the customer angle. The fourth type of CTO is the big thinker always innovating and stretching the boundaries. I am the third type, a customer champion. I think I'm this way because I've been on the business side as the customer and I've been on the technology side delivering trusted solutions. I'm always looking to solve problems through the customer lens rather than from a technical perspective.

Which emerging technology are you most excited about the prospect of? I hate this answer because it is so over-hyped, but it would have to be AI and Machine Learning. I think these technologies are over hyped because we don't have a lot of use cases that people understand. But, if you look at DocuSign Agreement Cloud vision, and the end to end system of agreement, we are starting to use these technologies to help bring a much higher level of effectiveness and efficiency to customers. Ultimately our goal is to leverage AI for smart contracts and we are well on the path to deliver this vision.

Are there any technologies which you think are overhyped? Why? [Laughs] I'm going to give you the exact same answer, I think AI and Machine Learning are over hyped in a big way, because people are talking about it without a) defining it b) connecting it to specific value delivery.

Another one would be blockchain. I started really digging into blockchain when I was in financial services during my PayPal days. I do believe that with blockchain there is a lot of opportunity, but in my view there's still a way to go before it becomes a practical, cost effective, everyday solution. The application of this technology is still in its infancy.

What is one unique initiative that you've employed over the last 12 months that you're really proud of? One of the first things I was able to accomplish when I first came in was to build discipline into the organisation around collaboration and cross functional execution. I think it's just a natural stage in every company's evolution, you get really good within your functional silos and as you grow you then start to have to work across functions, but you haven't started to develop the connective tissue to be able to effectively execute large programs. We are now in the first quarter of the year for DocuSign and we have already released more new products than we released in the last 2 years. I'm really proud of the entire organisation and the capability to bring innovation to market and do so in a collaborative and cross functional way.

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? My team leads our internal DocuSign on DocuSign program. DocuSign provides a digital transformation platform for all companies, and our company is no exception. We work to lead the way to demonstrate to our customers how to move from manual to digital across all their most important business processes. One of the great things about this platform is that it can be leveraged to grow revenue through decreased sales cycle times and improved customer experiences as well as reducing costs through automation and digitisation of back office processes. For my team I don't think about how we balance the two, instead I prioritise based on the specific workflows and end to end processes where we're going to get the most value. Sometimes that's on the revenue growth areas and sometimes that is in the back office, but what's fabulous is to have a platform like DocuSign that makes it so much easier!

What is the biggest issue that you're helping customers with at the moment? We are working to help customers understand that they all have systems of agreements - they just might not think of it in that way. DocuSign's biggest competition is paper and pen. We are helping customers see how they can take their manual end to end agreement processes and automate them in a way that brings a ton of efficiency to back office and even more delight to the customer. One of the great things about working at DocuSign is when I tell my friends I work at DocuSign, the first thing they say is "I love DocuSign!", and it's because the customer experience is so easy.

How do you align your technology use to meet business goals? In the past year and a half, we have moved to an agile delivery methodology. Following the principles of agile, a team has a product owner that often is from the business. The product owner is the decision maker and prioritises all the work that's getting done in the self-managed work unit called a scrum team. Because we have a tight partnership with the business as the product owner our scrum teams maintain a back log and roadmap that's prioritised from to meet the highest priority business goals.  

Do you have any trouble matching product/service strategy with tech strategy? This is a discipline that DocuSign has matured into over the last 2 years. We are now using Geoffrey Moore's zone framework for our strategic planning. Moore's framework breaks company initiatives into four different quadrants, the performance, productivity, innovation and transformation zones.  This framework has helped us align the productivity and systems projects that we're doing with the product innovation we're leading.

What makes an effective tech strategy? It all starts with with the company vision. The tech strategy has to support the company vision and it cannot be technology for technology's sake. It has to be built through the voice of the customer - understanding who your customer is and their needs.

What predictions do you have for the role of the CTO in the future? I think the CTO will continue to be closer to the customer. I think 10 years ago the CTO was a very back office, technology focused role and today and in the future the role will move closer and closer to the business and customer.

What has been your greatest career achievement? This answer is likely biased by the fact that my oldest daughter just got home from her first year at college, but in this moment I feel that my greatest career achievement has been that I've been able to have a very successful professional career and also raise two confident, independent daughters who see their mum as a role model. Could it get any better than that? I don't think so. It's so difficult as a woman going through your career and constantly having to make choices between your career and your family. I always felt so guilty and like I was screwing up. Finally, I've gotten to a place where, somehow, I've achieved career success and I've achieved success as a parent and it's amazing.

Looking back with 20:20 hindsight, what would you have done differently? I spent the first half of my career trying to out-man the men. I'd dress like the men, talk like the men and was aggressive like the men. That strategy worked really well when I was young because I think the men I was working with thought it was cute, but when I got to a more contemporary age, it became the absolute opposite of cute and became very limiting. It wasn't until I started to embrace the fact that I was a woman and stopped trying to be something I wasn't that things started to turn around. Slowly I learned to leverage the inherent skills that I have, both being able to stand up for myself and handle conflict situations, but also showing my softer more vulnerable side. I just wish I'd brought those two together sooner. I hope the women in technology and business today aren't making the same mistakes I did.

What are you reading now? I'm reading the book, Bad blood. It's the Elizabeth Holmes, Theranos story. It is fascinating and very hard to put down. She's a young woman, who is trying to make it in a very male dominated world right here in my backyard, the Bay Area. I'm also reading a novel called The Post Birthday World by Lionel Schiver and it goes back and forth between a person who took path A but the book shows you what life would have been like had the person taken path B. We all have our points in our life when we have major decisions to make and yet you can only take one path. One wonders what life would have been like if I'd taken path B? It's a super interesting way to see human dilemma being brought to life.

Most people don't know that I… I dance and do ariel silks (think circus arts). It is so beautiful when done with great skill, but it is really hard! Part of the beauty is that it looks so easy and yet it is not. It's made me mentally and physically a lot stronger.

In my spare time, I like to…Dance.

Ask me to do anything but… I'm fearless, but I do have a motto -- I'll do anything unless it could kill me.

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