Rachel Wong: Uber Eats City Manger & Co-Founder of Monday Girl

Could you tell us a bit about your career path and how you navigated that from when you graduated Western to now? 

Definitely not a linear journey. If you told me five or six years ago, when I first graduated that I would be where I am now, I’d probably think you’re crazy. I came from Western’s MIT program. It was a really interesting program in the sense where I could really hone in on my writing skills and my communication skills, but very vague in terms of its actual application. At the time, I was thinking that since I had a degree in media, I should go into media, and so I took a dive at Much Music in Brand Partnerships.

I noticed that start-ups were then also on the rise, and everybody was talking about unicorn start-ups. Uber always really stood out to me as being innovative and disruptive, and so I applied cold. I got the offer of a 3-month contract, and I was one of the very first people on the sales team there. I got to travel a bunch, I got to speak to a lot of restaurant owners, and I essentially became one of the founding members of what we now know as Uber Eats. The first three years I was selling and then after that I got to manage a team out west. Most recently, my role is a City Manager! 

Alongside my day job, I have been running Monday Girl for the past 5 years. To address part of your question of how I navigated my career after graduating, quite frankly there were a lot of gaps and moments of loneliness coming out of that university community. Our team at Monday Girl thought there had to be a better way to address those gaps rather than just mentorships and advice from cold LinkedIn reach outs. So we created an all-in-one career platform and in the past 6 months we created the Monday Girl social club with over 300 members, hosting events with partners from Microsoft, Google, and a bunch more really cool brands in Canada. 

Throughout these past 5 years, how has your personal definition of success changed from when you first graduated to now, if at all? 

When you’re younger and in school, a lot of it feels like a race. You think about “is this where you are supposed to be?” because this is where my friends are at and this is where I am. Then you graduate and you realize it is not like that at all. 

The mind shift for me after graduating was difficult because we were trained mentally that comparing ourselves to others was the way to see success. But as I worked, I realized that every single challenge or opportunity that you have is a chance to really learn. A lot of the non-tangible pieces of a challenge and a bad situation is the patience and grit you develop from that. I am not saying that anyone should ever have to put up with a bad or toxic environment, but I am saying that a challenging work situation where you are put up against something you might not know you can handle, take a deep breath and think about how during that process you might be gaining something so much more valuable in the long-term. 

For myself, early in my career I had to wear many different hats and thank god I did because I was able to exercise that in the current roles that I have now where I have to be more encompassing. It is interesting how early in the day, despite being just in sales I had to advise on strategy and a lot of other kinds of tasks.

What is your favourite part about Uber and what is it about the firm that makes you want to stay everyday? 

You are around people who are big foodies! But all jokes aside, it is the people. I am surrounded by incredibly smart people who are pushing both themselves and others to be their best self. The culture is such that everyone can learn from their peers. 

We often think of Uber Eats as a tech firm. How would you describe being in a sales role at a tech firm? 

Good question. I love the idea of getting more women into sales. I always joke when I interview someone for a sales team that most people do not grow up saying they want to be a salesperson. I think a lot of it has to do with the connotation of it and tech as a field is still relatively new so there are a lot of career paths that people are not aware of that are very real. There are so many routes you could go after becoming an account executive because it is kind of the first step of getting your foot in the door in a really cool tech firm. You get to learn about so many parts of the business.

In my team at Uber, I work with small and medium businesses, and so these are local favorites that you likely know and love to dine at. When we bring them onto the platform, it makes sense for them because it can help them expand and grow their business incrementally. 

Do you find that there is a big difference from sales at a tech firm than at another firm? 

It depends from start-up to start-up. I think tech has become this generalized term because everything is tech now whereas back in the day it was this hot thing. I would say that for sales in general, you’re working directly with people and the right customer needs this product or solution to help them. For me, I’m always going back to one of my core values of helping people. I do that with Monday Girl and with sales, I see and hear that all the time. You bring on a small restaurant and maybe before, not many people knew about them because they were tucked away in a small plaza. But after you bring them on to Uber Eats, now they have access to thousands of new customers. Suddenly it increases their brand awareness, revenue and maybe 6 months down the road, they are able to expand because of the additional revenue they bring in - thanks to Uber Eats. 

What makes a good salesperson? 

People think the best salespeople are good talkers. But that is not necessarily true. When you get into the industry, you realize the best salespeople are good listeners. There are many variations of the 80/20 rule, but in a strong sales conversation, the client or prospect should be speaking 80% of the time because they should describe all their pain points and walk you through their entire journey so that you can recommend them exactly what they need.

What has been the biggest challenge that you have noticed for women in this industry? 

It goes back to the connotation. I can speak for myself coming from an Asian family that sales does not fit into the version of what our parents want us to be. It should be seen as a really exciting opportunity for someone that is a new graduate to get their foot in the door and get the basics of a start-up. It is unique in that you get what you put into it and at the same time you get to learn all the ropes for the other sides of the business.

Pivoting to Monday Girl, what was the biggest thing you learned from working in an all-female team that you may not have necessarily learned in other teams, if any? 

As women, we experienced the problem of how it is really isolating and hard to start your career, especially as a woman. We are building the solution we wish we had when we first graduated and so it is very easy to understand the marketing plan, strategy, operations, etc because we are building for ourselves. 

Starting entrepreneurial ventures can be so difficult because you do not know so many things. Could you describe your starting journey with Monday Girl and how you were able to move past challenges of not knowing? 

It is crazy because when I started Monday Girl 5 years ago, it was a very different business in terms of strategy and what it meant to us. It evolved with time as we understood and validated the issue with more and more women. A lot of persevering through your business is making sure that you are addressing a real issue that needs to be solved and that can be hard without feedback. We are lucky to be in a business where we are always talking to our customers. The other piece is having an amazing cofounder! 

What kind of last advice would you give to those starting either their careers or their own entrepreneurial venture? 

Don’t do it alone. Join Monday Girl social club!