The Career Jungle Gym: How The Commons Mentor Nick May landed at the forefront of Product Operations

Mentor Spotlight

Welcome, Nick! Can you tell us a bit about who you are and how you’re involved with The Commons?

My name is Nick and I’m a Staff Product Operations Manager at Tonal and a Product Sprint mentor at The Commons. I’m based out of Toronto.

So, you started your career in theatre and in restaurants - can you tell us a bit about that?

My career has certainly not been linear in any stretch of the imagination. I like to say that it's been more of a jungle gym than a ladder. I studied Theatre for post-secondary education in New York city and like a lot of people in the performing arts, I found myself working in hospitality. I became the General Manager of a number of different restaurants, both in New York City and then Toronto. A few of those restaurants were ’concept restaurants’ that pushed me to flex a lot of my operational skill set. One of those restaurants was a not-for-profit social enterprise that supported new entrants into the workforce, another was the world’s oldest LGBTQ+ Bookstore that added a cafe/restaurant as a secondary revenue stream. 

What prompted your pivot out of hospitality and eventually into Shopify? 

Working in restaurants can be really exciting and fulfilling, but the world of hospitality can also be really tiring and 70+ hour work weeks aren’t uncommon. It wasn't something that I saw myself doing for the rest of my life. So, I dabbled my feet in the not-for-profit sector for a while. At one point I was also a buyer for Blockbuster Canada, and at another point, I found myself working at Shopify.

I knew a lot of people that worked at Shopify already. And while there wasn't one specific role that I felt was the best fit for me at the time, I just knew I wanted to work there. I had heard great things about the culture and so I applied to and started working in Merchant Success -  which was a good fit because working directly with consumers and helping solve their problems was something really familiar to me.

I thought that was a great way to learn a lot about the product and get involved with the company. Shortly after starting I transitioned to a role called an Expansion Pack, which supports leaders in the company with different strategic initiatives that they need extra eyes or hands on. Largely, the work that I found myself doing in that role was related to Product Operations, which didn’t have a clear place in the company yet. I knew that there was an opportunity to help support our teams in a new way. And, as the company started to invest further in Product Operations as a discipline, I knew that I wanted to help carve a space for myself in this high impact role. By the time I left Shopify, there were probably ~50 folks working in the product ops space, compared with the two or three when I first started.

What did you take away from your experience scaling the Product Operations team within Shopify? 

Through building out the org, it helped me to see the impact that Product Operations was having across the company, which was really exciting for me. It was particularly fulfilling to help define what ‘good’ looked like in the Product Operations space and to be a thought leader within that. As I started to dive a little bit deeper and understand how other companies defined Product Operations, I realized that no two companies viewed the role in the exact same way, which further propelled me to have a stronger voice in defining the discipline, not just at Shopify, but in the Product Operations space as a whole within tech.

I started networking, meeting others that were exploring Product Operations, and creating relationships within small different online forums and slack workspaces.

It’s one of the things that attracted me to coming to The Commons - so that I could share my experience, the best practices, but also learn from others as well and hear about what they’re doing in the Product Operations space.

After Shopify, you made the pivot to Tonal. What attracted you to that role?

When I made a transition from Shopify to Tonal, I was the very first Product Ops hire at Tonal. They were interested in optimizing their product org by driving efficiencies and improvements with best practices, systems, rituals, et cetera. I loved the idea of taking what I learned at a very large company and applying it to a much smaller one, knowing that not everything was going to work perfectly.

There were also opportunities to identify new ways to support our product teams on a much smaller scale and learn about the different pain points that a growth-stage startup goes through.

When you think about your pivot from acting and hospitality into Product Operations in tech, what skills were you able to leverage from your non-traditional background? 

I would say in hospitality, especially in hospitality management, you wear a lot of different hats and you're interacting with a lot of different people, whether that be with other peers, coworkers, customers or other stakeholders.

A few of the restaurants I managed operated with a Board of Directors, which meant having an added layer of governance in how we reported on our financials and key deliverables. Knowing how to engage with the board is very different from how you would engage with the Head Chef, or even a customer. So knowing how to flex those different communication styles is an important skill that I took with me. In tech, and Product Ops in particular, you deal with a lot of different stakeholders. Really knowing your audience is incredibly important in gaining trust and being successful in the role. 

Given the nacency of the function, how do you determine what it means to be successful in Product Operations?

It's tough when you have a blank slate in front of you. You can throw any sort of paint at it and it's going to look a little bit different, but is that good?

Efficiency is one of the biggest things I lean in to - making sure that our teams are operating at a rhythm that is comfortable for them, but also supporting them with what they need. Really knowing that the Product teams are getting what they need to gain alignment quickly is a way that I help measure my own success. For example, can we remove ambiguity, can we increase awareness of what they’re doing to drive faster alignment and approvals? And do our teams have the right tools to do their job effectively? You essentially want to keep finding ways to ‘out job’ yourself, by making sure the team has the right tools and rituals in front of them to enable them to move quickly. You want to make sure the team members have what they need to get through day one, two, three, etc. Then, you can come back and iterate to make an even stronger system.

And those efficiencies also apply to senior stakeholders as well - success for me also means making sure that audience receives the right level of information at the right times - including being looped in to help support teams through discussion around prioritization and resourcing to unblock and mitigate any potential roadblocks.

Ultimately, I want to make sure teams feel confident and comfortable, and that they're operating efficiently, knowing that unnecessary barriers have been removed. 

How might Product Operations teams vary company to company?

When you look across companies, no company builds products in the exact same way. For example, when you take something like an agile framework for building products, nobody follows it exactly. In my experience, people take the best pieces of it and leverage what’s going to work for them in their circumstance. That means we end up with a lot of different perspectives on what the product development process or lifecycle should look like. Helping to codify that process so that there’s one framework that people can approach across the company is really helpful for teams. They can then understand where they fit into the puzzle and how they can help move through that process successfully. 

How that ‘codified process’ will look company-to-company will be different based on their expectations, size and scale. Ultimately, Product Ops needs to be agile themselves to make sure that they're helping to fit the needs of the product teams, stakeholders, and ultimately the end-user the product teams are serving as well.

Can you talk about Systems and Product thinking and how those are important skills in Product Ops?

System Thinking: Having a really good sense of system thinking is an important piece of getting into Product Operations. That means understanding how an overall system works, how you can influence it and help change it, to make sure that you’re constantly iterating and making it better. But you also need to understand how it all fits into a bigger, broader system. It's easy to say ‘this is a process that we're going to implement’, but you also need to know how that process fits into the other systems. There will be other ways of working that are happening across the org, so it’s like trying to put together the perfect puzzle. It's not always going to be clean. And sometimes you're going to have to do things that are a bit piecemeal to get there. But having an end state in mind where one process or system flows into another is an important way to think about the work itself.

It's really easy to tackle really specific problems, but if you're only thinking about going really deep on something, you're not thinking about the broader picture all the time.

Product Thinking: Having a really good understanding of product thinking and how product itself works is important. Product Operations needs to understand Product Management. The two can’t work in isolation; they need to be joined at the hip to make sure that Product Operations is helping to support the needs of Product teams rather than just implementing change. Product Thinking helps to maximize the impact of Operations-focused teams. A friend of mine mentioned in a LinkedIn post that the best internal teams (Ops, Talent, Marketing teams, etc.) think and act like Product teams, which really resonates with me. For example:

  • They are clear on "why" they need to build or create something. They discover and diagnose issues and root causes. 
  • They design out solutions and they think about user experience and the best way for their ‘product’ to be used.
  • They test and iterate. They get feedback to understand what works. 
  • They are clear about what "success" of their solution looks like and they measure the performance of its ‘launch’
  • They iterate and adapt their "products" regularly

So what’s the difference between Product Management and Product Operations and what’s your take on the landscape for Product Ops roles?

Product Management needs to go really deep in their area of focus. They need to understand the way that product works inside and out. In contrast, Product Operations needs to be able to take a step back to understand the 10,000 foot view of the company, who all of the different stakeholders are, and what people across the company are doing. Their goal is to be a force multiplier and to do that, they need to connect the dots in order for everyone to have clear visibility into the path ahead

This is a really exciting time for Product Operations. There are a lot of companies that are starting to hire for this role and there are a lot of companies that don't really know what they need out of it, but they've heard of it or have seen Product Ops people be successful in supporting the growth or optimization within a company. That means there’s tons of opportunity to step into these types of roles and choose your own path in terms of where you put your energy and how you can have an impact. For those ‘choose your own adventure’ type people, it’s a great path to be on because there's nothing but an upwards trajectory in terms of what type of value you can bring to a role like this.

Let’s dive into mentorship - tell us more about this not-for-profit restaurant. How did it guide your views on mentorship?

The restaurant was called Hawthorne Food and Drink. It helped to provide on-the-job skills training and career mentorship to folks that had experienced systemic barriers towards finding employment - anything from being a new entrant to Canada or folks that experienced disability. We would tailor the training program to the individual to make sure that they were getting the most out of their experience. 

It’s an experience that really introduced me to the idea of mentorship and getting people really excited about the opportunities that were in front of them. I think that there's no one size fits all when it comes to mentorship or when it comes to how you work with other people. Being able to help develop and flex those different skills in that environment is something that I still bring forward with me in everything that I do.

Plus, the jungle gym approach to my career wouldn't have been possible without the mentorship of people that really believed in me and what I was capable of doing. Sometimes they played a more formal mentorship role, other times it was a little bit more informal, but knowing that there were other people that I could rely on and leverage to help upskill myself was an important way for me to help see what could be next for my career. They would help me dive into questions like - what were the things that I wanted to optimize for in life, or what are the ways that I could do things better?

Across all industries that I've been in, I've always found supporters of me that were willing to give me the time and energy to help with that. Mentorship is extremely valuable to me and being able to give back in a way to make sure that I'm sharing what I can with other people about my experience is important to me.

How do you think, from a mentorship and community perspective, The Commons can help people grow?

I think that there's value in understanding a lot of different people's lived experiences. With The Commons, you’re getting different perspectives. You're getting one-on-one mentorship time with people that you're directly connected with through your Sprint teams, but you're also part of a broader community which gives you the opportunity to learn from many others. That's something that I really love because my experience is unique to me and I think it's valuable when you put that together with the experience of others to create a well-rounded perspective for everyone in The Commons’ community. 

Outside of The Commons, how might you recommend people find mentors - should it be their boss?

I would say that having your boss as a mentor is a tricky situation to be in, and that's not the route that I would often recommend that people go down. Not to say that it can't work, but I think somebody who doesn't have a stake in the game is an important aspect of a mentor. You want somebody who's going to give you their unbiased opinion and feedback.

In terms of how to find that person, it should be somebody that you really connect with. You might have seen them talk somewhere, or you might have had some sort of engagement or connection with them - formal or informal. You need to find someone where you’d think: ‘Hey, I like this person, I think that they could get me, or I could have a really honest conversation with them’. Or, they could be someone whose career trajectory inspires you and you want to better understand how they were able to navigate it.

Additionally, it needs to be a high trust relationship. It needs to be something where you can be candid about your thoughts and feedback. It doesn't mean you need to find people that look like you or people who are doing the same thing as you, but people that you can just have a good conversation with. Those are the people you should be reaching out to. 

Lastly, be honest about your intentions. You should share what you really want to get out of the experience - more so than them just being a mentor - and ask if they’re really interested in supporting it. It’s a partnership really. 

How can someone make the most out of their mentor?

Plan ahead. If you have dedicated time for a session or with a mentor, share information in advance, come prepared and have questions ready. Know what you want to get out of the session and make sure that it's time well spent. Like I said, it's a partnership between two people, or even a group of people, and you really want to make sure that you're maximizing your time to make both parties feel like it was valuable. If you want someone to provide really good feedback on things, provide something for them to read in advance so that they can prepare for the conversation.

Honesty & transparency. If you're having a conversation with a mentor or mentee and you don't understand something, take that time to ask those questions and go deeper. It's really easy to say, ‘oh yeah. Okay. Thanks’ and feel like you got something out of it, but if you didn't truly understand something, ask more questions. It doesn't help anybody to just appease and act like you understand something if you really don’t.

If you’re interested in the red-hot Product Operations field and learning from mentors helping to define the discipline like Nick, join The Commons Product Sprint.

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