First job lessons: Seattle tech startup CEOs on what they learned from car washing, delivery, and more

Seattle-area tech CEOs, from top left: Icertis CEO Samir Bodas; Syndio CEO Maria Colacurcio; Qumulo CEO Bill Richter; Remitly CEO Matt Oppenheimer; Outreach CEO Manny Medina; Convoy CEO Dan Lewis; Zenoti CEO Sudheer Koneru; and Skilljar CEO Sandi Lin.

As summer approaches, many high schoolers and college students are off to their first jobs and professional internships across the country. Whether it’s washing cars or making metal casts and everything in between, there are lifelong lessons to be learned from a very first gig.

GeekWire asked a handful of CEOs running some of the fastest-growing tech startups in Seattle about their first jobs out of college, or even before.

Some noted how first jobs taught technical skills which were later applied to their company’s products. Other simply said they learned the value of a hard day’s work.

The main takeaway: there’s something to learn from every job. Here’s what the CEOs had to say (answers edited for clarity):

Icertis CEO Samir Bodas. (Icertis Photo)

What was your first job?

“My first job was as a programmer at National Instruments in Austin, Texas.”

What were your responsibilities there?

“I wrote device drivers for the IBM PC, as well as Apple Mac IIs and SEs.”

What did you learn from it?

“This role grounded my understanding of how computers run. Device driver and E/PROM programmers are closest to the hardware, and that bottoms-up understanding how a computer operates — from booting to loading the OS, to launching apps and beyond — is still immensely valuable, even in the era of cloud and AI/machine learning!”

How have you applied that experience to what you do at your company today?

“I was employee No. 42 at National Instruments (NI). It was one of the first software startups in Austin and the U.S., and NI is now a multi-billion-dollar company! The startup bug bit me then, and incubated for 16 years, giving me a deep appreciation of why grit, hard work, smarts, timing, and finally serendipity are essential ingredients for startup success.”

Icertis background: The Seattle-area startup creates software for contract management. Bodas founded Icertis in 2009; the company is now valued at nearly $3 billion. Bodas was previously CEO of Aztecsoft and Disha Technologies.

Syndio CEO Maria Colacurcio (Syndio Photo)

What was your first job?

“My first office job was in high school, working the phones at a kids’ talent agency.”

What were your responsibilities there?

“I was responsible for calling the parents of the kids who did not get cast. I didn’t get to call the parents of the ones who did get cast, unfortunately. I got yelled at a lot.”

What did you learn from it?

“My biggest learning was how to stay true to a message in the face of adversity. It also taught me — at a pretty young age — resilience and goal setting.”

How have you applied that experience to what you do at your company today?

“Today, I am still pretty great at staying on message and staying focused on what I want to say — regardless of the reaction from the other side.”

Syndio background: Its software helps businesses eliminate gaps in pay disparity. Colacurcio previously worked as a director of retail communications and partner brand for Starbucks.

Zenoti CEO Sudheer Koneru. (Zenoti Photo)

What was your first job?

“My first job was as a software design engineer at Microsoft in the Windows NT team at that time (what is today the core Windows Operating system).”

What were your responsibilities there?

“My role was to develop the “Distributed File System” in Windows. It is very deep device driver level work in Windows which controls how your files are located across the network and optimized for performance and easy access across a large enterprise.”

What did you learn from it?

“I learned to be really detail oriented. This kind of work needs developers to be very precise in development work and to write code that is very optimized since any sloppiness in performance here affects all applications on Windows. The need to measure your performance and be very deliberate in thought on how to best optimize my work was key.”

How have you applied that experience to what you do at your company today?

“This experience really has carried through into all my walks of life and business journey. The habit of being very detail oriented in all aspects of business planning and pushing the organization and leaders for plans that are thought through with deliberation has been a deep habit for me.”

Zenoti background: The Bellevue, Wash.-based startup creates software used by more than 12,000 spas, salons and wellness businesses in 50 countries. It valued at more than $1 billion. Koneru, co-founder and CEO, was previously at Microsoft as a director and product unit manager.

Convoy CEO Dan Lewis. (Convoy Photo)

What was your first job?

“Besides being a newspaper route understudy to my sister, I drove a van in the summer delivering office supplies and pallets of paper all around the Seattle area to help out our family business. This was a job I shared with my brothers, sister and cousins.”

What were your responsibilities there?

“In some ways, my responsibilities were not unlike those of a local truck driver today. I had to understand my drops and design the best route so that I would get it all done in time (we didn’t have smartphones, we used Thomas Guides to navigate); I needed to physically load the van in the correct order for my route, and then unload and unpack the items for each customer; I had to collect signatures to confirm delivery, deal with customers rejecting items, etc. An average day for me was 10 hours.”

What did you learn from it?

“I learned a lot about warehouse operations, logistics workers, and last mile delivery during that time. Everyone buys office supplies, so I got to learn about a broad range of companies across different industries, from biotech to shoe manufacturing to video game developers.”

How have you applied that experience to what you do at your company today?

“While I didn’t drive a big rig, the job did give me insight early on into the challenges that truck drivers face. We’re committed to addressing these challenges and always building a better experience for carriers.”

Convoy background: The digital freight startup facilitates transactions between trucking companies and shippers. It was valued at $2.7 billion in November 2019. Prior to co-founding the company, Lewis was general manager of new shopping experiences at Amazon.

Skilljar CEO Sandi Lin. (Skilljar Photo)

What was your first job?

“Transportation analyst at Cambridge Systematics.”

What were your responsibilities there?

“I helped city and state governments make better use of their transportation dollars by modeling strategic investment scenarios over long range planning horizons. For example, I supported the Florida Department of Transportation to develop its Strategic Intermodal System and mapped database schema for the Pontis Bridge Management System, used by over 45 state DOTs (now known as AASHTOWare Bridge Management).”

What did you learn from it?

“Governments are severely underfunded when it comes to infrastructure. Much of our infrastructure was built in the 1950s with intended 50-year design life, so much is now functionally obsolete or structurally deficient. Plus, even though it’s far more cost-effective to invest in regular maintenance, it’s more exciting politically to replace a bridge after letting it deteriorate. This was frustrating to observe as a taxpayer.”

How have you applied that experience to what you do at your company today?

“Working with governments led me to business school. I believe I can make a greater impact on a faster timeline in the corporate world. I also saw the difficulty in any organization for maximizing for the long term. Just like governments don’t invest in maintaining infrastructure, all too often companies don’t invest in ongoing customer success (Skilljar helps solve this problem!).

From a culture standpoint, my first company was also hierarchical and title-centric. This has led me to prefer flat organizational structures that place emphasis on ownership and results.”

Skilljar background: Lin, co-founder and CEO, originally worked at Amazon but left to pursue a startup that took many forms until it became Skilljar. The company provides back-end tech and software to help companies build training and onboarding programs. Skilljar raised $33 million in funding after the pandemic created increased demand for its services.

Outreach CEO Manny Medina. (Outreach Photo)

What was your first job?

“Tool and casting company — I was an assistant machinist. We made the casts for cola caps and soap.”

What were your responsibilities there?

“I had some experience with metal machines but not making casts because they have to incredibly exact. I had a boss who had the patience of a monk and saw me mess up so many casts. He gave me a task and watched me fail — from sharpening my tool to failing at making the cast — and then he would correct one thing. It wasn’t until my third month that I really got it. He was so deliberate in seeing me fail and try.”

What did you learn from it?

“If you’re going to be good at a job, you have to get failing as part of the job. It’s part of education. You fail, and you make it right, and you learn.”

How have you applied that experience to what you do at your company today?

“I embrace failure as we were building a company. Failure has a place and it should be used. It’s a dog-not-barking problem — you don’t know what your team is missing if there’s no failure. You don’t get to invent if you’re not failing. And in our business, we have to invent.”

Outreach background: The Seattle software company helps sales professionals land more deals. It recently closed a round of funding that pushed its valuation to $4.4 billion. Medina, co-founder and CEO, previously worked for Amazon Web Services and led a division of Microsoft.

Remitly CEO Matt Oppenheimer. (Remitly Photo)

What was your very first job?

“I was a ticket ‘runner’ for a local travel agency in Boise, Idaho. This was back when you had to have a physical airline ticket to board a flight.”

What were your responsibilities there?

“Once a customer purchased a flight through the travel agency, it was my job to hop on my bike and deliver their paper boarding pass.”

What did you learn from it?

“I learned that paper airline tickets are wildly inefficient! But really, that’s when I first started to envision how technology could improve efficiency and customer experience across all sorts of industries.”

How have you applied that experience to what you do at your company today?

“When I started Remitly, I wanted to disrupt the centuries-old global remittance industry. In those early days working as a ticket runner I really felt inspired to find ways to use technology to improve people’s lives. Today, at Remitly, we use technology to offer immigrants around the world more inclusive and accessible financial services. Through technology and innovation, Remitly makes international money transfers faster, easier, more transparent and more affordable for customers.”

What was your first professional job?

“My first job after college was with an investment consulting firm, Cambridge Associates. Most of my clients were endowed nonprofits, foundations and universities, and the returns we achieved for them went back into helping further their missions, so there was a lot of meaning to the work we did there.”

What were your responsibilities there?

“I was a consulting associate so I would help advise clients, usually investment committees, on asset allocation, investment manager selection and spending policy, among other needs. I also got involved in a few special projects related to socially responsible / ESG investments.”

What did you learn from it?

“I learned that purpose and meaning in work is paramount. While my day-to-day activities were very technical, I felt a sense of fulfillment knowing that my work was playing a direct role in helping my clients achieve their missions.”

How have you applied that experience to what you do at your company today?

“Lead with purpose. Life is too short to not do something meaningful that makes a positive difference in the world.”

Remitly background: Its mobile technology lets people send and receive money across national borders. The company reached unicorn level last year and plans to go public. Oppenheimer, co-founder and CEO, was previously at Highway 12 Ventures in Idaho and led mobile banking initiatives at Barclays Kenya.

Qumulo CEO Bill Richter. (Qumulo Photo / Andy Rogers)

What was your first job?

“Washing cars in the neighborhood. $3 for 1 car and $5 for 2 cars.”

What were your responsibilities there?

“They were similar to now. Quality, customer service, relationship building.”

What did you learn from it?

“I learned that I would rather work from my brain instead of my hands. I learned self-reliance and the value of a hard day’s work.”

How have you applied that experience to what you do at your company today?

“I have always believed in the value of hard work. Lucky people work really hard.”

Qumulo background: Qumulo was founded in 2012 and reached unicorn status last year. Its software helps companies manage and store large file data. Richter was previously a venture partner at Madrona and president of Isilon Storage Division of EMC.

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