Leader Spotlight: Jumping straight into product leadership, with Ophir Wainer

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Ophir Wainer is VP of Product Management and Growth Marketing at Compass Digital, a digital and technology innovation company within Compass Group. She started her career in law as an associate at Meitar Law Offices, Israel’s leading law firm. Ophir moved into tech while pursuing her MBA at the University of Toronto and joined Platterz (now Thriver) before joining Compass Digital.

In our conversation, Ophir talks about how starting her career in product as a product leader influences her approach to the craft. She shares her experience building zero-to-one products and talks about the benefits of the experimental nature of startups. Ophir also shares how she leverages her team’s skills to be a more effective leader.

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‘How product chose me’

To start, could you say a little about Compass Digital?

Compass Digital is part of Compass Group, which is the largest food services conglomerate in the world. Any large business usually has food as part of their offering, but most don’t want to have their own food operations. A hospital wouldn’t have a head chef and hire employees to run their own kitchen. Compass would come in, put our offer out for a bid, and run those operations. We have tens of companies in the group who do that in different fields and areas. Our prerogative at Compass Digital is to create products in that intersection of food, hospitality, and technology.

Compass Group serves over 10 million meals a day with 98 of the Fortune 100 companies. The biggest companies use us to feed their employees — whether they be a sports venue, corporate office, university campus, hospital, etc. Compass Digital’s goal is to ask, “What would make our guests feel seen and help us provide them with the best food, hospitality, and experience?” This is how Compass Digital works to contribute to this grander vision.

You have a very interesting background having worked in legal early on in your career. How did the transition into product come about?

It’s a funny story because when you start going to law school, you make a choice that has a pretty distinct path. You finish law school, do your articling, get an offer, join a firm and start to build that trajectory to partnership. It’s a very clear path. I was very driven, and when I finished law school, I got a job with the top-ranking law firm in Israel. But when I reached this big milestone, I realized that even though I loved the firm and practicing law, I was using a smaller set of my skills.

I decided to both give law a full chance but also put an egg in another basket. I stayed with the law firm for a few more years and I’m happy that I did. But ultimately, I decided to get an MBA and transition geographically to North America, as well as into the tech field.

In terms of choosing product, I would say it chose me. All I knew was that for my MBA internship, I wanted something different. I ended up joining a startup here in Toronto, which, funnily enough, operates in the food space as well. I was a direct intern to the CEO, essentially acting like an internal consultant.

At the end of the 10-week internship, I said that I was going back to business school full-time but would love to stay part-time. He said, “I have a better idea, Why don’t you take all of product on?” I decided to do it. I had a full-time job as a full-time student, and that was my introduction to product.

Relying on the team’s skill sets

Another interesting thing about your career journey is that you’ve actually never worked as a product manager. Most people don’t jump into product as a product leader. How has that shaped your approach to product development and team dynamics?

I think in some ways, it has made me a better leader because de facto, I’m unable to micromanage. I’m always growing really strong product managers and product leaders under me, and I fully rely on their skills. It’s very clear what my added value as the leader of the team is from a product perspective, as well as their value as PMs.

I don’t think that to be a really good product leader you had to write stories in your past. There are a lot of things that you need to know. You need to be aware of the details and learn a lot about your team and their day-to-day to lead them, but you don’t necessarily have to have done every task yourself to empathize with them. I can lean on their expertise and bring in the rest from my perspective as the leader.

When you’re hiring for your team there are certain traits or characteristics that you look for to round out the overall offering?

I always hire people with strong communication skills. I also love curiosity in candidates, because the experience is almost a given. You have to have the relevant experience to even apply for the job, most of the time. When I interview, I look for those softer things — how do they think about the problem? Are they collaborative? Are they curious?

You’ve expressed a strong commitment to mentoring and developing your teams. How do you think about or promote continuous learning and growth for your team members?

The best way to learn is by doing. Growing your team is about providing opportunities. Mentoring on dry land won’t get you a good swimmer. You have to be doing things all the time and sometimes that means that you invite your team to watch you in what you do. Like, “Hey, this is a really interesting meeting. Come be a fly on the wall.”

I start with opening doors to let people watch what I do and help me with it. When I feel that the person is ready and they’re expressing that they feel the same way, we flip it. They do it, and I watch or help. It’s very much centered around doing because I feel like mentoring and giving advice are not always tangible.

The experimental nature of building zero-to-one products

You’ve been part of a few zero-to-one launches in your experience, both in very large companies as well as more of an early-stage startup. Could you talk about some of the differences and similarities that you’ve experienced?

In a startup environment, you get to break things more. It’s easier to be more experimental. The accountability is significantly lower because you’re out of anyone’s sight — no one’s looking at you. If you fail, there are almost no implications. In a corporate environment, even at that zero-to-one stage, you’re never really an underdog. You’re expected to deliver your first proof of concept to a greater level of refinement than what you would at a startup.

On the other hand, when you’re in a corporate environment, you have significantly more resources. Money is part of it, as well as access to advice and mentors. The fact that you have a lot of people who are very well aware of that industry means you need to know how to ask questions and avoid biases, especially when you’re trying to build something new. But, you can tap into incredible things.

Getting your first users can be easier if you’re an unknown startup versus when you are operating in an environment that’s stable and established. Both have pros and cons, but it’s always exciting to be in the early stage of a product regardless of the environment.

Statistically, a lot of zero-to-one products fail. Do you have an example you could share from any of your roles where you worked on launching something from the ground up and it didn’t work out?

100 percent. When I was working at my MBA startup, I had a side project that was a potential product of ours. It was what made me want to stay on during the school year to continue working in the first place, but it fully flopped. The idea was to create meal cards as an employee perk based on Visa. We were building off those payment rails and added our own rules to say, “OK, you have $10 every day for your lunch or $5 for your coffee. That should be consumed within the radius of your office and work hours,” and so on.

There are a few reasons why the product failed — one was that we were trending to launch in April 2020 toward the start of COVID. However, one of my learnings was that a good idea for a product in and of itself is not a reason enough for you to build it. You have to think about the competencies of your team, the position of your company, the other products you have, and what the resources would be to make it successful.

Being a marketplace technology company going into payments, we didn’t have an unfair advantage in terms of our product scale, engineering scale, go-to-market, etc. We were probably not in the best position to execute a payment product successfully.

That’s why today, when a good idea comes about, I ask, “Is this a good idea?” I also make sure to question whether or not we should be the ones to execute it and make the idea into a product. I’ve found that the number one rule of product is don’t fall in love with an idea.

When you’re growing something from zero to one in an established company vs a scrappy startup, do you find you adjust your leadership style?

Yes, it’s definitely different. As a leader, you need to ask yourself, “What does this product and this team need from me?” One example of something that’s different in a startup versus a corporate environment is communication. It has to be significantly more intentional when you’re in a corporate environment. You want to be much more specific and intentional in how you explain to other teams what you’re doing, how you want them to support you, how they can participate, and what areas they should not participate.

Communication and closed-circuit marketing

At Compass Digital you work at the intersection of hospitality and technology. Generally, you can’t speak too much about the products that your team creates. How do you effectively market something that you can’t talk about?

You could call it closed-circuit marketing. The Compass Group is comprised of hundreds of thousands of people. We find other ways beyond a billboard or an ad to communicate with our potential users — often finding places that they’re already at like internal conventions or leadership meetings — and finding ways to insert ourselves.

In that sense, it’s very similar to traditional marketing because we have to identify where our customers are and how we can communicate value to them. The answers to the questions are more unique because it’s not as simple as just saying, “Oh, our customers on Facebook. Let’s put an ad there.” In a lot of ways, it’s almost more challenging, but also more pure to think about marketing from that perspective.

Do you have any strategies that you’d be comfortable sharing about things you found effective in building intrigue or customer engagement?

Three things come to mind. The first is word of mouth. This is especially important for us as we grow. For word of mouth specifically, we have to think about who is really loud. When we did our last big product launch in October of last year, it was something that we only piloted in pieces. It was rather risky, and we had to make the decision of whether to keep quiet or pilot with a crown jewel type of user. If we were successful, word of mouth would spread rapidly, but if it flopped, we’d get the same effect but in a negative light.

We took the risk because we knew that if we got our first 10 users to feel like this launch was exclusive and had a prestige factor, that would be positive enough and word would spread.

The second thing is that all of our communication is rooted in value. Our pilots are product pilots, but they’re also heavily involved with our marketing team because we are always looking to understand the thing the user is most delighted with. If that thing is value, we get actual impact, and the communication already includes that success story. This compliments word of mouth very well because it goes along with a trusted relationship with other users. It’s almost like a closed community,

That leads me to the third piece, which is that our users are rather close to each other. We have tight industry connections that we tap into and leverage. We ask where the people are at, so whether it’s internal webinars or mini-conferences, we make an effort to be there. That way, we’re able to tell our stories when our users are already gathering.

The ratio of personal and professional growth

It’s clear that you put a value on learning and development. What are some areas that you’re personally working on? Do you have some areas that you’re trying to stretch or expand your knowledge on right now?

I believe that personal and professional growth can’t be decoupled, or at least that they’re a very fixed ratio. What has really helped me grow is anything that has to do with either the arts or sports. These areas help me to expand my perspective on how I do things. In the past year, one of the things that really expanded my perspective is horse riding. I used to do this as a child, but I stopped because one, my brother was better than me, and two, I fell and was genuinely too scared to get back on the horse.

Recently, I was with my dad, who has continued riding. He just kind of poked me and said, “Come on, come ride with me!” and I got back to it. Picking up a new sport as an adult is definitely humbling, and it’s a great reminder of how growth isn’t linear. It’s almost like learning a language. It’s helped me choose to be brave and I think it’s also expanded my perspective.

These are the kinds of things that eventually bring a lot to how I view work. You come in after you have these kinds of experiences, think about them, and you’re like, “Yeah, growth is not linear. I’m going to double down on persistence with this product because it’s possible.” Of course, I keep up with industry trends and the product community, as well as reading professional literature, but I find that I get the best ROI when I draw conclusions that aren’t already spelled out for me.