Meet Holly, The Commons alum and Operations Manager at Instawork. After excelling in the Strategy + Operations Sprint, Holly pivoted into tech when she landed a role on her mentor’s team
Holly’s career path in one line: Bachelor’s degree in business -> Supply Chain Analyst (2 years) -> Operations Coordinator at Instawork (the first Ops hire in Canada!) -> Operations Manager at Instawork
Read on to learn more about Holly’s career journey, her experience working at a startup, and how she made the most of The Commons community to launch and accelerate her career in tech.
Why did you want to pivot from supply chain operations into tech?
I started my career in a supply chain ops role in a massive company where I was one of thousands of employees. I was working on a tiny piece of a massive pie and I was feeling disengaged, especially during the pandemic when we transitioned to work from home and there was not much work culture. During the pandemic, tech was booming and people started talking about it more and I became interested. I initially had my eye on the big tech companies, like DoorDash and Uber, and I saw that The Commons had a good community of people from those companies, so I decided to join to learn more about opportunities in tech.
What was your experience like during the recruiting process, and how did you land the job at Instawork?
I started my job search by applying and interviewing online, sending resumes to open job posts. I found the recruiting process to be really draining. It takes up a lot of your time which can be difficult to manage if you have a full time job going on as well. So I was pretty discouraged after feeling like I was going in circles with recruiting. But then my friend told me about The Commons and I saw that there was this network of relevant people there that might help me out.
After completing the Strategy + Operations Sprint, The Commons helped me create an online portfolio using Notion and shared it with the community. Suddenly, people were sharing my portfolio with hiring managers. It actually worked out that my mentor at The Commons, Alex, had recently started a new job at Instawork and was hiring for his team. I really enjoyed working on his team during the Sprint and he ended up hiring me as an Operations Coordinator, Instawork’s first Ops hire in Canada!
Speaking of mentors, what was it like to work with a mentor in tech?
My mentor, Alex, is a really great mentor. He was the best part of my experience at The Commons. Working with him really resonated with me. He gave very specific and actionable feedback. We always ended our meetings with two to three action items and everything is always actionable, feedback-oriented and objective.
I remember the first week we worked together in the Strategy + Operations Sprint, I presented the first part of my analysis and he gave me some tips on what I could improve and what areas I could dive deeper on and I realized that I wasn't used to getting such constructive feedback. So I went back to my analysis, implemented his feedback and presented my new findings the next week. He was impressed that I took the advice to heart and praised the improvements to my analysis. I remember that making me feel so happy. It was such a nice experience to get specific, actionable feedback, implement it, and then receive praise for the improvement I made.
How did the skills you developed during the Strategy + Operations Sprint help you with your transition to tech?
I remember the first draft deck we presented to our mentor. It had a lot of information on it and I applied what I learned from my business school background. He observed that we spent a lot of our presentation presenting the data and very little on our takeaways and recommendations. He helped us contextualize the problem and let us know that if this was a real project at a real startup, the stakeholder would probably know a lot of this background information and we should spend more time talking through what our hypotheses were and our recommendations. It was a bit of a shock to me because I was so used to spending time reporting data up to senior leaders because in a more corporate setting where they may be more detached from day to day operations. So that helped us understand what it might be like to work at a startup where the leadership is closer to the problems we are trying to solve, and interested in what action items can be taken from the data.
When I was interviewing at Instawork, they asked me, what was this project you did with Alex, and what was the most important thing you learned from it? Based on what I learned in the Sprint I was able to say, “focus on the action items. Develop a hypothesis, use data to prove or disprove the hypothesis, and present the key recommendation”.
Now that you work in tech, what skills did you learn in the Strategy + Operations Sprint that have helped you in your day to day?
Definitely SQL and communicating using data. Being able to have the data at your fingertips when you need it is so helpful for getting things prioritized and aligning stakeholders. It’s very important to be able to communicate data in a way that makes sense to people and provides next steps.
It may seem basic, but I think getting used to many of the tools used in startups was helpful. Like going from Outlook and Microsoft Teams to Slack, Gmail, Zoom, and so many more like Asana, Calendly and Zapier which I’m now obsessed with. I remember when I first joined The Commons and I logged into the Slack, I got like a ping from the team and I'm like, “This is weird. What's going on? What are all these channels?” I didn't know how it worked. It was good to learn about some of those tools at The Commons so that I knew what I was doing when I needed to use them in my job at Instawork.
Since starting my role in tech, I got promoted from Ops Coordinator to Ops Manager in 6 months, then to Launch Ops Manager 5 months later. Getting two promotions in my first year at a company certainly isn’t usual. I will say I don’t think I am extraordinary and it didn’t take hard technical skills or years of specialized experience to get me here. All I’ve done is take the hustle mentality, grit, positive attitude, and growth mindset I fostered at The Commons and applied it to every challenge and task that was thrown my way. Anyone can be successful in a tech role if you have the right mindset and willingness to learn.
Last question: What advice would you give to someone who’s looking to pivot into tech, and thinking about joining The Commons?
Do it, just do it. It's so worth it. If you feel like you are in a rut and you can't make moves in your current recruiting situation, it will bridge the gap. It will fill the white space in your knowledge and grow your network. The community is full of supportive people and you'll be very surprised at how well supported you are by the people in the community, regardless of their title, their seniority, or how long they've been working in tech.
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