My Career To Date
I admit, my career path is more of a career wandering. Here I outline my roles, the lessons I learned, and how I've navigated from support to engineering to operations and back again, twice.
I was faced with the “What do I do with my life?” question all soon-to-be college graduates face. In 2008. At the height of the Great Recession. With a math degree. Before data science was cool. I decided to snooze that decision by approaching one of my professors for a letter of recommendation to Michigan State University’s Master of Industrial Mathematics program. The program sounded like fun, had an incredible job placement rate, and it would buy me two years to wait for the economy to get moving again. I did not expect his response. “That will be a waste of your talents. I will only write you a letter for a PhD program. Besides, those programs will pay you to get a degree.” So, I applied to a few of those instead. After graduating with my baccalaureate, I spent a few years working toward that goal – going as far as my talent alone would take me. It turns out, math isn’t fun when I have to work at it – which is why I have a Master of Applied Mathematics (universities tend to give you one of these along the way) and mark myself as ABD: I’ve completed all the courses and all the tests; I just didn’t write a dissertation (and I never will).
As it happens – that four year “snooze” was fortuitous not just for the economy, but also for the skills I developed. During my time, I refined my talent for writing code – specifically high-performance algorithms, but also some custom VBA code in Excel. (Actually, for the engineers reading this, I didn’t learn what a breakpoint was until half-way through…so I got really good at mentally interpreting how code functions.) I also developed training skills, and patience, working as a teaching assistant and tutor.
Leaving the PhD program, I got a job at a local mid-stage software startup: Expion. I started right as that organization was shifting from a rather boutique operation, focusing on local brick-and-mortar companies, to a more enterprise-grade solution – landing Hilton, Mattel, and several other big clients shortly before I started. I initially applied and was hired to the Sales Engineering role – Anything with engineer in the title will work I naively thought – but they created a new role on my first day with the rather ostentatious title of “Critical Care Technical Engineer” (I relabeled this on LinkedIn to make to more SEO friendly). Essentially, they needed someone who could work with the Customer Success Team to translate customer issues into technical tickets for engineering, then validate the fixes once they were deployed. Expion being a startup software company, I was a busy person. I became good at working with customer-facing teams and engineering teams at the same time, in no time.
A management role opened several months later, and my initial successes made me an ideal candidate. I was offered, and accepted, the role of “Marketing Insights Manager”, and kept my IC responsibilities as well. (My LinkedIn profile injects another role between the first and second, but that was not an official title. I added it to show a progression of responsibilities…and to align with a substantial merit increase.) This was my first role that included real “management” responsibilities – specifically career pathing and development. I was lucky that it did not require hire/fire decisions as the team was already established – with great team players – and we were able to keep up with the company’s growth by injecting efficiencies in the service offering. This helped me establish my management style without having to cope with these more challenging scenarios. Evidence suggests, and I’d like to think, I did well in this role – the CEO asked my manager, the Director of Customer Success, to let me run the QA Department. In Engineering. At the same time. After being a manager for less than six months.
So, I ran a second team. I identified a strong performer within Marketing Insights, with a strong customer focus and sense of ownership, and promoted him to Team Lead. I did the same within QA – a strong customer focus being paramount for this role as well. Decentralizing the day-to-day management duties was the only way I saw to keep up with such disparate orgs. This freed me up to think more about strategy which, in turn, led to the establishment of a 24x5 Technical Support Team – as there was a strong need for this as we went global. We created an amalgamation of product support and [AWS] system monitoring – writing bug reports and testing deployed fixes in production and using proprietary tools to handle systems issues that occurred overnight.
During the time we were building this support team we were interviewing for a Director of Production Engineering to oversee myself and our DevOps Manager - who also ran corporate IT. After a couple of interviews (the CTO, CEO, the DevOps Manager, and I interviewed these candidates), I approached the CTO. “I can do this job. What do I have to do to prove to you that I can?” That reads a lot more confrontational than it was; in conversation it came across much more sincere. I wanted the role and felt I could do it; I wanted to prove I could do it. He spoke with the CEO, and they told me, “If you can do the job for six months without the title, it’s yours.” My approach to this was to work much more closely with the DevOps Manager and his team, an organic transition given we were continually refining the Product Support Team’s tools and adding to the list of system’s issues they could directly address.
I wanted to understand the DevOps work as best I could, foremost because it was interesting and I knew almost nothing about it, but also because having a baseline allowed me to provide another perspective on the problems they were solving. This, in turn, led me to ask a lot of questions – intrinsically giving them the authority – and making only occasional recommendations – rarity making my ideas inherently more valuable. After a few months, the DevOps Manager was approaching me for advice on matters before the CTO. I’ve adopted this approach to taking on new teams ever since.
Within a year Expion was bought by Sysomos. My team and I spent the next several quarters resolving some of the issues that come from startup expansion – homogenize production environments, automate maintenance steps, stabilize systems, etc. I, or the DevOps Manager, went from getting an after-hours call once a week to once a quarter. (Brief aside: these rarely impacted the customer by the time we were called but would have if we weren’t.) I also built out a QA Automation program during this year, and established several professional development practices. Otherwise, it…was…boring. By and large, the Sysomos leadership let Expion languish and did not provide clarity to our executive management team on the direction and strategy of the overall company.
Which is why the Expion CEO spent a few months planning and negotiating with Sysomos’ private equity owners on a new direction for the company: Expion leadership will be better for Sysomos. The CEO called me on a Saturday and asked if I could meet him at his house. I drove over, and he showed me his plan for the takeover – and he showed me the gap in the team: Vice President of Operations, along with the teams this role ran (Sales Ops, Deal Desk, Business Intelligence) that were not going to report directly to him (Customer Success). “I don’t have anyone to run this team. Can I count on you?”
“I’ll get it done.” I then left his house and went home to look up, "what is sales operations". Fast-forward one year, admittedly one of the best years of my career, and we were in final talks to have Sysomos acquired by Meltwater. (Backing up a moment, our responsibility – as dictated by the private equity board - was to make Sysomos a sellable asset within twelve months. We did this through R&D efficiencies and improved GTM strategies – and a few other things.) A condition of the sale was to make Sysomos a profitable company or rather, detail what steps were to be taken after acquisition that would make Sysomos a profitable division. Many of the details are confidential, but one of the items was to reduce our Business Operations headcount by two. A resignation solved one, with one left. I chose my seat, as it was redundant in a merged organization. I could have displaced one of my direct reports, but I didn’t see the morality in that decision – I opened myself up to new opportunities on LinkedIn.
Someone at a local startup named Surprise HR reached out. The concept sounded interesting, and the problems challenging, so I joined. Despite the connections I made and the skills I picked up, I consider this to be the worst decision of my professional career (and I accidentally crashed a server servicing one of Expion’s largest clients…in my first year…so I’ve made some impressive mistakes). The then-COO-turned-CEO established the most top-down management style I’ve ever seen and had a mind-bendingly mercurial temperament. This was largely irrelevant for me in my first couple of years as he mostly ignored customer operations – customer success, which I worked closely with, and customer service, which I built and ran. We also ran Customer Service out of a different office for a couple of years, allowing me to establish what I felt was a decent culture within the team (albeit intense given the economic constraints of hiring Support Agents in the US). I didn’t realize the level of micromanagement the CEO exhibited in areas of the business he cared about, for want of a better term, until he tapped me to run Demand Generation.
“We’ve spent months looking for someone who understands our business and is great with numbers, and I have that resource right here. Will you be our Director of Growth?” At the time my exposure to Marketing was through managing the Marketing Operations Specialist at Sysomos, which is to say I knew the theory and I understood the numbers, so this sounded like a great opportunity for me to learn things and experiment with digital marketing while making a huge impact. Wrong. It turned into an opportunity for me to learn Marketing Operations on-the-fly so I could implement the CEO’s ever-changing ideas, or rather the ideas of the Chairman - who directed all business activities. Thankfully, after only a few months of 16-hour days, these two decided they liked the tangibility of Sales (AEs and SDRs) over the amorphousness of marketing. (Paraphrasing their beliefs – which I do not share, “I want to know exactly who is receiving our messaging and exactly why someone bought our product, or it doesn’t matter. We can't do that with marketing.”)
And so, the Director of Growth morphed into a Director of Sales Development into a Director of Sales Operations which, in retrospect, I’m very happy for. Single-handedly setting up a rigorously tracked and tallied multi-channel digital marketing program is, for me, a multi-quarter endeavor…at least (time I would have appreciated and maximized but was not allocated). Doing the same for a multi-channel SDR team is, for me, somewhat trivial. Establishing the Sales Automation tools (Outreach, ZoomInfo, LISN, 6Sense), and the cadences and messaging therein, was old hat by this point in my career. The sales operation at Sysomos was much more established than the marketing presence – having three distinct GTM motions in sales and a relative shoestring budget in marketing. But after a while I grew quite bored with this function. The company was small, and the niche offering was going to keep it that way. The culture was brutal and was seriously impacting my mental health. I had to get out; I had to reset.
Around the time I made this decision, a friend of mine was discussing a company he’d invested in – Scinovia. “Why don’t you talk to them? They might not need you right now, but it will be good to make a connection and see what they’re working on.” And, in truth, he was right; they didn’t need me right then. But the tech was fascinating, and I was itching to learn something new. (For the coders reading this, I learned C++ in a week and CUDA in 30 days.) They were able to match my compensation, albeit as a contractor, so I left Surprise HR (which had rebranded to Surprise.com but was otherwise the same) to become Scinovia's first professional engineer hired outside of the VP of Technology.
I really enjoyed my time at Scinovia. Granted, there were only three of us, with a handful of interns at any given time, and I didn’t manage anyone – in truth, it was an enjoyable paid vacation. I accomplished a lot, and learned a lot, but after the first six or so months it became monotonous. Every day was grinding on computation algorithms. Try this. Try that. Try this and that. Try that and this. Try some other things. Then mix those things with this and that and try again. It was not fulfilling. I’m not cut out for research; if I was, I’d have completed my PhD. Sure, I’ll experiment for a few weeks, perhaps a couple of months, but after a year my mind was going numb. Compounding this professional frustration were fundraising challenges; I felt it was time to move on.
Welcome to Clipboard Health (CBH)! I applied to the Director of Strategy and Ops role at CBH and was presented with a thought experiment – a pricing problem. Part of CBH’s interview strategy is to send a homework assignment as the first step of their recruiting process (after they read your application – I assume, but before any interviews). Conveniently, I had just contracted COVID, so I had time on my hands. I put together a compelling slide deck and supplemental spreadsheet detailing my thoughts and landed my first interview. The Head of Product opened the interview stating they’d just filled the position (a fortuitous event, all things considered) but that he still wanted to talk. That interview was followed up by a call with the President later that day, then another with the President that same day (he had a meeting in between as I understand it), then another with the President the following day. (I stress the title because I only spoke to two people, and the first for 30 minutes.) “So what are you looking to do? I could see you helping in Sales, in Marketing, in Support. We could use you in any of those.” My response was simple. “Put me where your biggest fire is.”
During my tenure at CBH I was the only experienced operations professional at the company, among between 800 and 1200 people. (This is a bit hyperbolic. There was a Salesforce Admin on staff when I first joined, but they resigned effective a few weeks into my time there. And I believe they were considering a DevOps group around this time as well that was established shortly before my parting. They also established a Sales Ops team of sorts, more data entry specialists, toward the back half of my tenure.) Initially, I chalked this lack of operational hygiene up to a radical growth curve that caught the company unawares. However, after observing the Strategy and Ops team focusing purely on product strategy – often ignoring scalability concerns – and the Sales Ops team being built by tenured account executives (with no background in Salesforce, Analytics, or Sales Ops) and after seeing several of my initiatives fail to gain traction at the executive level (the primary reason being the lack of ROI, as support initiatives were measured against R&D initiatives in the form of raw dollars) – I began to see it as the consequence of deliberate choice.
I could speak at length regarding my perspective on the role operational strategy plays in long-term company growth. For now, I’ll state succinctly that second-, third-, and nth-order factors need to be considered as much or more than first-order factors (and first order and first principles thinking should not be conflated). My time at CBH left me with a genuine appreciation for systems-based thinking, and how it is decidedly more difficult to articulate than I expected. It also reinforced my leadership principles as well as my understanding of the role leadership plays in an organization. I’ve also come to appreciate the intuition I’ve developed over my career is not commonplace, and that detailed writing is the most effective means to align on objectives when this intuition is not shared.
In the end, my approach to problem solving and the broader organization’s approach to problem solving were too different – often diametrically opposed (e.g. jack-of-all-trades vs separation of concerns) – and my leadership approach of decentralized authority was not shared by executive leadership. When my manager, the Head of Customer Operations, was tasked to reduce support costs – which had ballooned over 2022 – my role was eliminated and I was laid off. In many ways it was an enjoyable experience but, in the end, the outcome of my time at Clipboard Health was a refined understanding of self and a renewed appreciation of my values.