Five things I come back to. They are not rules — they are the shape my experience settled into after two decades of building organizations and the systems they run on.
I often quip that the “T” in CTO stands for therapy, not technology; in so much that much of my responsibility is to promote collaboration amongst everyone in my organization and throughout the company. It’s absolutely imperative I stay heart-centered and in the moment to ensure I’m able to provide necessary feedback, wanted or otherwise, in a manner that can be heard. My goal is not to be nice — everyone should be nice — but to be kind; in short: tell the truth, as I see it, to help ensure everyone is set up for success.
In this regard, I’ve become an ardent student of human psychology in order to get the most of our my teams. While I buttress my actions in a practical understanding of Maslow’s hierarchy as well as psychological safety, I ground myself with applied mechanisms and processes that can be whole-cloth used by any leader within my organizations. This kind of psychological safety creates space for individuals to hone their skills of self-awareness and self-actualization. Only in this way can any of us expect to realize our highest self, and this is why I consider my calling to be heart-centered leadership.
It’s common-sensical to create this kind of place to work as it brings out the best in everyone. And that is ultimately my goal as a leader: foster high-performing teams.
I’ve been fortunate to make a career as a technology executive since 2015 while working entirely from our home in central Washington. As an autistic person, I’ve found that remote work is an absolutely critical ingredient to help me maintain composure for my people. It’s not that I cannot work effectively in-person as I did at companies such as Boeing, Amazon, and Microsoft; but working remotely makes me more effective.
At RealSelf and other companies, I’ve helped transition companies to 100% remote-first.
An article I wrote for GeekWire in response to some of the backlash to remote work. Remote work is not a panacea, but I’ve developed some very practical tips that anyone can use to find their mojo in a remote world.
I wrote this a few months into the COVID-19 pandemic to share my many years of experience working 100% remotely as a technology executive. At the time, everyone was new to remote working and struggling to find their stride.
A companion piece on how to create culture when everyone is working remotely. Maybe not too surprisingly, creating culture in a remote-first environment is not different than in-person, albeit you need to be very conscious of everything you do.
As an engineer and operations manager his entire career, my father was deeply involved in TQM (Total Quality Management). I recall quite vividly and fondly him sharing his thoughts, experiences, and even reading material with me in my very formative years as a pre-teen and teenager. In particular, I recall our discussions on Theory X versus Theory Z, which have played heavily on my leadership philosophy.
Many years later I would work as technical Japanese interpreter at Boeing, working alongside Shingijutsu USA consultants to help mature the Boeing Production System, a variant of Toyota Production System. That year of intense working relationship with our Japanese consultants rekindled in me a passion for lean thinking. After a year as an interpreter, I returned back to engineering, transitioning from aerospace to software engineering where I introduced the very nascent, barely formed ideas of agile programming to Boeing.
Ever since then, I’ve been deeply involved in both working within and creating lean environments and processes. I worked as a senior software engineer in a paired programming environment to launch AmazonFresh. When I was technical program manager overseeing Amazon’s detail pages I reduced our deployment cycle time from 4- to 2-weeks and then to 1-week. I’ve worked inside an Azure incubation team consulting with TechStars’ Andy Sack where I created a dummy company and walked the local shopping mall to interview parents just to garner market signal on possible product ideas. I’ve created entire teams, services, and processes from 0 to 30 people in under a year for Sears, to growing the technology maturity of Varsity Tutors and RealSelf to 100s of technologists all while ensuring my teams deploy multiple times a day.
Lean is in my blood. I do not know any other way how to think or operate.
My academic engineering background spans multiple advanced engineering degrees from computational fluid dynamics and magneto hydrodynamics, technical Japanese with focus on Japanese space development, and software engineering.
My professional career pulls a thread from these in the loosest of ways, having focused on:
At Amazon, I was part of the original engineering team that proved out AmazonFresh in the greater Seattle market. We built our own WMS (warehouse management system), and in the process of proving it out, it was possible to be unit-economic profitable. I subsequently launched AmazonTote, another pilot program in the greater Seattle market before taking over as technical program manager of Amazon’s RCX (Retail Customer Experience) where I oversaw Amazon’s detail product pages (lion’s share of all Amazon traffic).
From Amazon to Xbox to Sears to Varsity Tutors to RealSelf, I’ve been deeply involved in nearly every aspect of supply-demand matching. Especially with the most recent experiences, I’m exceedingly well-versed with demand aggregation, whether through organic or paid traffic, along with applying data-at-scale to do demand-shaping to improve conversion yields.
Not all marketplaces are created equal. Commodity-based marketplaces such as Amazon.com are trivially easy when compared to services-based marketplaces where there is large variability in supply quality, liquidity, et cetera.
Every endeavor first starts with finding signal. Have we discovered an unmet need? Have we created a customer experience that addresses this unmet need? And have we convinced our customers that our experience is the best on the market? Once we have signal, it’s critical we rapidly scale every aspect of the company.
Unfortunately, the attributes that help discover signal are often in conflict with those required to scale. In my over twenty years I’ve spanned both signal and scale. I’m uniquely positioned to help early-stage startups find signal, and once found then ensure they scale to enterprise-grade scale.
There are three areas where I’ve spent the past decade focused on building scale:
Since my days at Sears, I’ve been the key technologist leading the charge to decouple monolithic systems, whether at enterprise- or startup-scale into modern, enterprise-grade cloud SOA (services-oriented architecture). This requires a significant amount of discipline and a multi-year roadmap that takes into account: 1) software development lifecycle; 2) process maturity; 3) operational maturity; and, 4) talent maturity.
Technology is a deeply collaborative undertaking, requiring everyone to be open and engaged in working with each other. More so, even more important than reporting structure is our operating structure. This takes a great amount of finesse to intimately know my people, thus knowing how best to deploy them to the greatest effect. I’ve built teams from scratch and grown to 30 people in under 12 months, and taken teams of 30 and grown them to 150 at a global scale.
There is no greater resource than our people. If we are not investing in them, both for today and the proverbial tomorrow, we ultimately discover they will leave to grow their careers. I take seriously everyone’s career development. I’ve been deeply involved with the career leveling at Varsity Tutors and RealSelf, and consistently have significantly better retention than the industry averages.
Whenever I’m given the chance I’ve spoken to others around the world (wide web) about my thoughts on leadership and technology. I think it’s exceedingly important to be vocal about more holistic and effective means to being innovative.
I covered a few mistakes — what can I say? I’m an overachiever — including my time at Amazon working on AmazonTote and how there is such a thing as “too little UX friction.” We also dig into psychological safety and how COEs (celebration of errors) help create it.
Nell Derick Debevoise interviewed me for a Forbes article on my variant of COEs, or celebration of errors. COEs are a straight-forward mechanism that takes the classic root-cause analysis and turns it into psychological safety, engendering a culture of learning through failure.
Listen to the last ten minutes for my top 5+1 recommendations to being an effective leader. The first thirty cover psychological safety and emotional intelligence, delivering results, building remote-first cultures, and me being autistic and the implications for people leadership.
Listen to the last eight to ten minutes as I speak on my leadership philosophy.
A work-in-progress on the things I keep telling people leaders — the lessons, the uncomfortable truths, a little maths, and what to go read next. 124 pages and counting.
The leadership model I used with a 150-person globally distributed organization, as presented internally.
Nell Derick Debevoise interviewed me in 2021 as part of her research for her book. At the core of her research is authenticity in leadership that connects ourselves and our work to the greater world around us.