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Career CloseUp: Director, Customer Advocacy


My name is Michelle Sawa, I am the Director of Customer 360 Advocacy at Upwork. What I do day to day at Upwork is I'm overseeing all of the qualitative research that comes in. So any of the feedback that our users are leaving on our site, in any NPS surveys, any surveys that they're doing, that is being funneled over to my team. And our job is really to try to understand what are the trends, what are people saying, are there issues, bugs, points of friction, points to celebrate, praise that people have coming to our platform. And so my team is really–we’re overseeing all of the insights. So we do things like send out the newsletter to the company to help everyone understand the different trends that are happening. And then teams are also coming to us to say, hey, we want to understand more about this specific market or these specific users, what data do you have?


And so our team is looking at all of the human stories and qualitative feedback to piece together that picture and share those insights that can help product teams or other teams at the company design for our users. Let's say we have thousands, maybe 3,000 pieces of data coming in every single day, one person can't possibly read that all so how can we use tools and automation to make that easier to understand and track trends? And that's really what my team is working on now with our natural language processing vendor: is how can we categorize all the feedback that's coming in so that it's easier for our team to act on it. And it doesn't require a ton of manual work to try to understand what people are saying at scale.


The most fascinating part, maybe surprising, about customer experience is that it really is like a chief investigation, right? You're trying to figure out what are the numbers telling us, what are the people telling us, what are the employees telling us and how can we triangulate this picture of the true customer experience for teammates and the experience that we're delivering with the marketplace? What I love about my role and probably not something that you would see in a job description for a customer experience role is really just, you know, trying to deeply understand the way that an organization works. 


My background has been a winding road and my background is advertising and business and I worked at an entrepreneur center when I was in college and I loved it so much. The experience that helped me the most in my career was teaching. When I first graduated, I was working in email marketing and just thought you know what, there has to be more to life than just sending emails. So I became a teacher and it was just an amazing experience. I taught in a charter school system in Houston and wow what a humbling year. I say it was, it was my boot camp here, the hardest year of my professional life.


You just learn so much about human psychology and how to really give all of yourself to help the kids around you learn and thrive and grow. Afterwards I realized, whoa, that was also the most transformative because now I'm taking all those lessons into the business world where people don't know, they haven't had this experience of needing to stand up in front of 300 kids every day and redirect behavior, get people to feel passionate, engaged and listen. And I think that is one of the most valuable skills that I now bring to the business world is just that interpersonal communication: how to teach, move people and bring them along with whatever you're trying to do.


Then my partner who was my boyfriend at the time, who is my now husband, had an opportunity to move abroad to Rio de Janeiro, Brazil and so he said Michelle, do you want to come with me? And I was like, oh yes, I'll do anything. This has been really hard for me, I need to like, you know, find myself again. And I remember my school being like Michelle, you don't have to go with him and I was like, I think this time I do, I think I need to follow my heart. I’m such a fiercely independent woman that I thought for sure I was going to be the one like charting all the places that I would live and all of that. And I think it's been surprising and delighting in ways that I couldn't even imagine. It's almost like every time we've moved, it's been an opportunity for me to reinvent myself and take the things that I learned. And I think it's given me such a degree of confidence. 


Something that really helped me was before I went to Brazil, I had connected with someone who was a freelance writer. She was a yoga teacher and I saw her at a marketing event and I was like, hey, I took your yoga class, tell me more. And she had the coolest life, she was teaching yoga, she also was a freelance writer. And I remember meeting at a coffee shop and I was like, okay, you have to tell me everything. How did you make this work? Tell me about the legal side, about taxes, about all these other things. And it was like the confidence and the lessons that she shared with me, I was like, okay, if Carly can do it, I can do it.


And so I think that's the most beautiful thing about sharing your story is that you can inspire other people in ways that they never thought possible. I think about how many people in my life are like, wow, you're choosing love over your career. Like you could be further in your career if you just stayed in one place and as someone who has kind of like a wild streak and rebellion in me, I was like, no, I'm going to figure this out. I didn't have a work Visa, I couldn't speak the language, I had to think about, okay, what are my marketable skills? And I didn't want it to be the end of my career and I know there's a lot of people who choose and they say, all right, I'm gonna be a tag along spouse, I'm gonna volunteer and I will just, you know, fill my time in that way. And I was like, no, I'm going to make my career work. 


So I thought about my marketable skills. I reached out to companies, a company that I had previously worked for and another company that I was considering working for years ago and just said, hey, I'm a freelance writer now, I've always loved writing, I can write blogs, press releases, anything that you want. And so people said, all right. And it was just such a fun year where I had total flexibility and freedom in my schedule. I was able to do things locally, like go to the beach and go out to lunch and learn Portuguese. And then I had, you know, a couple of great hours of writing and work time, which is like the perfect schedule for the deep work that I needed to do. 


One of my clients was a financial advisor and he said, Michelle any money that you invest in your action, getting a master's, taking certificate programs, that is going to pay off tenfold. So my advice to you would be okay, if this is the path that you want to do, think about the things that you’re passionate about, learn as much as you can, that's how you can truly innovate your career by being the person who's in the room who has the solutions, who has the connections and network. And it's not necessarily having the answer in your head, it's having the resources and the resourcefulness to go and find, where does this already exist? Am I looking at you know Harvard Business Review articles, am I getting connected with the certificate program, am I reaching out to a mentor that I met through this network? So that would be my advice: lean on all of the education and the education system that already exists and invest in yourself and your future.


I ended up running a website for moms with one of my clients and then with one of my other clients, I had said you know what, I think this is the year I'm going to write a book and he said wait a second, I want you to write my book. So then I spent the rest of my year writing a book and you can get it on Amazon, it's called Car Dog Millionaire and it is a marketing book for car dealers. After that year that I spent working on all these projects, we moved back to the U.S. and I said you know what, this is a lot of fun. I had made more money than I was– than I did when I was teaching and I was just having a ton of fun. I just could not imagine a more flexible life for me. So I got connected with the startup ecosystem in Houston and I just started working for some of the startup companies. So they would come to me and say, hey can you write my website? And something near and dear to my heart is qualitative research and really deeply understanding humans. And so I would say all right, I'm gonna write your website but first let me talk to some of your existing customers or people that you're trying to sell to, I want to see how they would explain your product and what you truly do.


And so I would start all of my engagements with this qualitative research. I would give them this insight summary, do a presentation with them, share these insights, and they ended up being more valuable than the copy. I would then show them how to use these like the pain points and the words that they used to create marketing copy that really resonated and I was having a blast, it was so, so much fun. From there, one of the startup companies that I was contracting with brought me on full time. That was a transformative experience. So I spent four years there just building so many different teams for the company, helping them with marketing, positioning, and helping them with onboarding, product marketing. And then landed in customer experience and that led me to where I am today for Upwork. You know, we're working, our marketplace is freelancers and clients, which is a world that I already know. And just really digging into understanding: what are the human insights that we gather from all of our users, what's the story that they're telling us, how can we use that in our marketing and our product development, in all parts of our business to get closer to the people that we're designing for?


Something that I think has been really valuable for me and something I've learned over the years is that no matter where you are right now, nothing is permanent. Everything is temporary. It's something that you're moving through right now. So even if you feel like you're stuck in a place in your career where you're like, this is not what I want to do. Like when I was teaching, when I was in it, I was like this is not what I want to do, right? But I stuck around, I did it, I did the hard thing and only after could I look back and see, oh my gosh, that was the lesson.