About

Driven by curiosity, obsessed with systems, and wired to figure things out.

Sheryl Ryan, Operations Integrator

sheryl@infrastructurebydesign.com

I’ve been obsessed with systems design and solving complex problems since I exited the womb. My mother used to love telling everyone how I’d be on my father’s lap for hours, mesmerized by the gears on his watch and examining every element, from the rotating second hand to the intricate clasp. And then, by two, how I’d sit in the middle of the floor fitting together a puzzle too advanced for my age, oblivious to the cocktail party around me.

That endless wonder and extreme focus have served me well over the years, and I’ve always been able to figure out the things others struggle with

Explorer’s mindset

In my personal life, curiosity is how I ended up joining the Marine Corps after college (instead of Wall Street). And how I ended up living/working in Australia, South America, and across the US states. It’s how I learned to build instead of buy, fix my own plumbing and electric, and turn ugly landscapes into neighbors’ envy.

In my professional life, it’s why my resume looks like a Jackson Pollock with crazy smatterings of unrelated industries that, when you stand back and squint, strangely work. How my experience canvas ended up this way is anyone’s guess. I just sort of magnetize random projects and dive in. (And, in the process, build new skills, gain new perspectives, and elevate my ability to solve whatever oddity comes next.)

Snapshot

  • Hands-on exec for early-stage startups, especially post-seed to Series B
  • Solutions architect, data whisperer, and efficiency junkie
  • Trusted partner to product, engineering, sales, marketing, success, HR, and finance
  • Ambiguity translator structuring creative chaos into actionable strategy
  • Zero-to-one builder and connector of dots
Operations generalist & solutions architect

How it manifested

Early in my career, I was managing compensation plans for a dozen or so sales teams at a publishing company. But in my data tinkering, I’d automated away most of my job. The universe must have noticed the gap in my schedule, because before I knew it, I was investigating years-overdue advertiser payments for our Asia office.

A few months later, my boss called to let me know that the APAC GM was able to recover quite a lot of money thanks to my work and finally close the books on this burgeoning A/R issue… and he also wanted to ask whether I’d considered letting him know I was working with this team on the other side of the world (before that was a thing). To which I replied, “Nope”. It hadn’t dawned on me to tell him.

Problem found me, I fixed it. No biggie.

A recurring theme

Later, at my first startup, our analyst stopped showing up. He was farmed out to us from our incubator and was randomly part-time, so no one really noticed at first. Our (quasi) parent company had put him on another project without letting us know, and he wasn’t responding to emails. But our paid search team needed answers, and those reports weren’t building themselves. So, I learned SQL to get the data I needed, HTML to organize it in a practical way within our homespun reporting suite (based on how the team managed their day), and CSS so it wouldn’t look so horrific. (Gratitude, Barnes & Noble!)

When the Ops team heard I’d built a better reporting suite than the analyst who ditched us, they dropped their wish list on my desk. I was architecting all sorts of infrastructure for the company and was swamped. But by this point, I knew the database so well that I was able to squeeze it in. While I was at it, I decided to tie together the rest of the company’s data and build our financials from the bottom up, so our bookkeeper could adequately reconcile with QuickBooks and leadership could have a more comprehensive view of the business.

At that point, my CEO popped in to ask where our analyst was… and whether I’d considered letting him know I’d taken over the role. “Nope.” Hadn’t dawned on me.

Problem found me, I fixed it. No biggie.

Trial by fire

That kind of thing happened a lot over the years, except that, eventually, I learned how to manage up.

I led a highly successful 80-person sales team for a few years, though I’ve never sold anything directly. I’ve stepped in as interim Head of Marketing for ~2 years, despite never having another marketing role (while simultaneously managing post-M&A for a company we’d just acquired and building a new client-facing department to support an impending product launch). I’ve also served as CPO/CTO to lead the development of a new recruiting technology for a legacy staffing agency, despite not having a traditional product or engineering background.

Essentially, I’ve worked within or directly managed nearly every function across an organization, solving the challenges I was hired to solve, plus a ton that randomly found me.

Multiple perspectives when developing solutions; I bring all the lenses.

Jack of all trades, master of many

Generalists are often labeled as “a jack of all trades, master of none“. But I’ve gained a long list of ‘specialist’ experiences and ‘specialist’ skills over the years that allow me to morph into whatever role is needed in the moment and dive deep to figure out the challenge at hand.

Thankfully, this ability pairs well with early-stage startups, where challenges are unpredictable and priorities shift quickly. And with growth-stage teams spinning up new initiatives that require early-stage focus, without distracting everyone from the core business.

I jokingly tell people, “I bring all the lenses.” But it’s true. Being a natural polymath allows me to bring a range of perspectives, see around corners, and tackle challenges that others simply can’t.

What’s brewing at your org? I bet I can help. Let’s hop on a call to see how we might work together.