My dad would make us kids write down our goals on New Years. 1 year out, 5 years out, 10 years out. At 14 years old, I couldn’t see beyond the next couple hours so naturally, I thought it was stupid (it wasn’t). Fast forward to really since college graduation (2010) - I have been doing this goal setting with some serious disapline, even if they don’t materalize, it’s important to get a white board and write down some goals so you can keep that part of your life organized. New Years and birthdays (summer time for me) always seem to get me in this personal/career planning mood, so here is a bit of a story about the last 10 or so years for me.
![](https://substackcdn.com/image/fetch/w_1456,c_limit,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F1107fd67-072b-4f8d-8a69-65c91560f69d_2048x1536.jpeg)
From Cycling Across America to Leading Digital Transformations
Every career path is unique, and mine has been a ride—literally and metaphorically. Over a decade ago, I captured my coast-to-coast cycling adventure across the United States, and the lessons from that journey still resonate with me today.
The Early Days: Embracing the Unexpected
My career began in retail at an Irving gas station and in the media and tech section of Best Buy. These roles taught me the foundational elements of customer service and the importance of empathy—a skill that has been invaluable throughout my professional life. At Irving Oil, we relied on SPIFFs for high customer service ratings, which worked well until people stopped giving us ratings altogether. This early experience underscored the importance of consistent customer feedback and engagement—a theme that would recur in my later roles.
Building Expertise: The Transition to Tech
Transitioning from retail to technology, I took on roles that allowed me to delve into social media strategy and solution engineering. At companies like Salesforce and Oracle, I not only honed my technical skills but also learned to navigate complex enterprise sales cycles - ya win some, and ya lose some. My time at Salesforce, where I advised on social strategy and spoke at Dreamforce, highlighted the evolving nature of communication and the need to stay ahead of technological trends.
While the transition from Salesforce to Oracle was a decent move (despite leaving lots of stock options on the table… rip) I was a bit naive in thinking the product would be easier to sell just because it was a better product. I really learned just how special we had it at radian6, and then later at Salesforce with our marketing team, despite maybe not having a better product than Oracle, the Salesforce social product was much easier to sell. People loved Salesforce. Not so much Oracle (at the time, 2014-2016).
The DocuSign Era: Leveraging Technology for Efficiency
Joining DocuSign marked a significant shift in my career. I have become much more technical at DocuSign, which was a true goal of mine. I touch many systems now as oppose to just marketing and social media tech from years prior. And now with ChatGPT (if you’re annoyed by all the buzz around ChatGPT I’m sorry but you’re NGMI) you can learn and troubleshoot, and BUILD PRODUCTS, so much faster then before. There is no modern technical challenge that cannot be researched with this tool. Anyway, as a Lead Solution Architect, I design Contract Lifecycle Management (CLM) technology to strategically place vital contracts and data in connected systems, enhancing efficiency and decision-making processes - aka make people’s lives easier, aka, I sell software.
One of the most rewarding aspects of my role at DocuSign was partnering with internal teams and customers to solve complex problems. This has exposed me to various APIs and technologies, reinforcing the value of continuous learning and adaptability in tech roles, and of course, getting the win in the deals — which is nearly as rewarding as winning state championships as a kid time and time again.
Lessons from the Field: The Importance of Empathy and Adaptability
Throughout my career, one theme has remained constant: the importance of empathy and adaptability. Whether managing customer experiences during hands-on workshops or influencing internal teams during technical sales cycles, understanding and addressing the needs of both customers and colleagues has been crucial.
The Personal Touch: Why Customer Service Matters
Reflecting on my journey, one standout memory is from my time at Irving Oil. Our older demographic became our most loyal customers, and we ensured they received the best service possible, often going the extra mile to provide them with the support they needed. This taught me that genuine empathy and personalized service could turn customers into long-term advocates.
Looking Forward: The Future of Digital Transformation
As I continue to navigate the ever-evolving tech landscape (lol) From social media consulting to eSignature and more complex contracting and data management needs, to traditional and now more modern AI, the opportunities to leverage technology for meaningful change are limitless. My goal is to continue building, and researching solutions that not only meet business needs but also enhance user experiences in significant ways.
Here’s to the road ahead and the many opportunities it holds.