Meet Chong: Corporate Finance to Head of Operations at a Startup

Skillfuler Story

Meet Chong, a Skillful alum and the Head of Operations @, a restaurant technology platform startup. Chong pivoted from finance into tech after joining our Fall 2020 cohort of the Core Sprint! 

To summarize Chong’s career path in 1 line: Bachelor’s in Business Administration ➡️ Product & Investments at BlackRock/TDAM (launched over 30+ investment products!) ➡️Skillful ➡️Strategy & Ops @ Uber Eats (managed day-to-day market operations and helped to service expand hours across Canada) ➡️Head of Operations @

Read on to learn more about the framework that helped Chong make the decision to pivot into tech, why being Head of Ops at a startup feels like drinking water out of a firehose and how the Skillful network helped Chong land not one, but two intros that changed the path of this career. 


What inspired you to want to pivot into the tech industry? 

I’ve always been interested in learning and trying new things. I have a few friends in tech and I’ve always loved hearing their stories about what they do on an everyday basis and the impact they are able to make. I’m also a big fan of Bezos’s “Regret Minimization Framework” (see more here) and I knew I would definitely regret not challenging myself and going into a more disruptive space.

Tell us more about your Skillful experience. 

I found the move from Finance to Tech extremely tough, partially because I wasn’t really sure what I wanted out of tech (other than just being in tech). By joining Skillful, I was hoping for three things: 1) to really understand tech and specifically roles in tech like Business Operations, Chief of Staff and Product Operations, 2) Be able to connect with motivated, like-minded peers and share/learn experiences and 3) ultimately be able to leverage the skills and network from Skillful to find a job (spoiler… 1,000% ROI for sure).

My mentor during Skillful was Charles, who used to be at Uber Eats in the US (and my referral into the company!) who is now at Netflix! The team project was a challenging but fun experience to go through. In the beginning, it was like most group projects I’ve been involved with, differences in viewpoints, differences in energy levels, etc. But we were all able to band together (especially after that mid-point checkpoint) and really come together as a group, enhance each other’s ideas and deliver an awesome presentation :)

Skillful has the most tight-knit, helpful and smart community that I’ve ever been involved with. There’s a lot of value of course in the sprints, workshops and the final group project, but just the community alone, with a diverse group of individuals across the world, all in different industries, roles and seniority levels, is extremely powerful and not to be underestimated. Plus, I’ve never had a community where if I wanted to reach out to anyone, they’re always willing to chat with me and share their experiences.

I can’t tell you how many times I’ve joined programs where people pitched this great product/service, I get all excited, then I feel almost abandoned once I’ve paid. The Skillful team is always supportive, always willing to lend a hand and provide advice and are strong advocates for your career journey. That’s hard to find.

You joined the Strategy & Ops team at Uber Eats shortly after finishing the Core Sprint at Skillful. How’d you land that role? 

I did about two months of job searching before Skillful. After Skillful and completing the team project, I was quickly able to get an interview with Uber Eats (thanks to my mentor Charles for that initial push) and with his and James’s help (another Skillful mentor currently at DoorDash), I was able to successfully break into one of the top tech companies out there! When I was looking to make my next potential move and considering options, one of the jobs that was posted in the Skillful network is what I ended up going with, successfully making the pivot to a seed stage startup called as their Head of Operations.

Chong is onto his 2nd role in tech, <1 year after making the initial jump. Chong stayed involved with the Skillful community even after he landed his role at Uber, which opened up a new opportunity as Head of Operations at 

As the Head of Operations at, a startup, I’m responsible for wearing a number of hats on an everyday basis. Outside of Product/Engineering, I am involved in every other aspect of the business, whether it’s Business Operations, Strategic Initiatives, Accounting and Finance, Analytics, dealing with investors, Customer Success, Legal, Human Resources, etc. At a high level, my job is to keep the WISK machine running and enhance the capabilities of everyone around me to be their very best (and to eventually 10X the growth!).

I found the role through the Skillful network - it was posted on the Skillful job channel. Got an intro directly to the CEO and the rest is history! I met with the CEO and the CTO. They gave me access to data (similar to the Skillful project!), which I analyzed the data and provided actual strategies on how to improve the business. 

What were your first few months at like?

The old adage is “drinking from a fire hose”. Being at a startup feels like drinking from an entire fire truck, if that makes sense! But despite the firefighting, constantly changing priorities and chaotic environment, it’s been an amazing few months so far. I’m getting a chance to put in place a variety of operational frameworks to help drive growth, reduce churn and better enable our team to 1) be more efficient with their day to day and 2) help lead our startup from a seed stage currently eventually to a successful Series A, B etc.

What advice would you give to someone who is embarking on a job search or career pivot?

“It might not be the easiest journey, but hang in there and keep going… you’re smart, talented and deserve the very best. You may face a lot of rejection but that’s their loss… just keep moving ahead and enjoy the ride, you’ll definitely come out a better person from it.”

Lastly, I hate to quote Drake but YOLO. My belief is that life is too short and too precious to spend on something you don’t like and will regret later on. It may seem scary taking a leap of faith, but as long as you keep believing in yourself and trust that you got this, you will have this. 100%

And now, to learn a little bit more about Chong - what makes him tick, what inspires him and what he's currently listening to:

🤣 I love to laugh, have a good time and no matter how tough a situation is, I try to find the positives in the negatives

🤯As someone who made the pivot from Finance to Tech and love to learn, I’m always blown away by the new things I discover on an everyday basis

😑This is my face when I’m dealing with my hundredth fire on an everyday basis, but after a brief few seconds, it’ll then turn to this 😁

🎙My favourite podcast is How I Built This by Guy Raz

🌟 A CEO or leader I admire is Elon Musk

💬An inspiring business quote: “The way to get started is to quit talking and begin doing.” – Walt Disney (strongly believe in action > words)

This interview has been edited for style & clarity.

Interested in more?
Meet Jonathan: Entrepreneur, Professional Athlete and now, Product Owner at a Fintech startup
Skillfuler Story
Meet Jonathan: Entrepreneur, Professional Athlete and now, Product Owner at a Fintech startup
Meet Jonathan, a Skillful alum and Product Owner at Neo Financial, a Fintech startup. Jonathan is an entrepreneur, professional athlete and now, a Product Owner at a startup, after joining the November ‘20 Core Sprint and September ‘21 Product Strategy Sprint. 
Meet Armish Sehar: Corporate Finance at a big Telco to BizOps at a Startup
Skillfuler Story
Meet Armish Sehar: Corporate Finance at a big Telco to BizOps at a Startup
Meet Armish, a Skillful alum and Ops Manager at Sampler, a startup that digitizes DTC product sample delivery. Armish pivoted from consulting into the tech industry after joining the Spring ‘21 Core Sprint.
From Strategy Consulting to BizOps: How Julia Di Spirito Found Her Career Passion
Skillfuler Story
From Strategy Consulting to BizOps: How Julia Di Spirito Found Her Career Passion
When Julia graduated from university with a business degree in hand, she went into management consulting. But after a few years, she came to the same conclusion that so many young consultants do: this wasn’t exactly what she wanted to work on for the rest of her life. There was, however, the small question of what was next?
Skillful logo
HomeOur SprintsHow It WorksOur CommunityOur Mentors