Jessica Tiwari, Upwork: “It’s important to recognize that you will never be the expert”

Jessica Tiwari, Upwork:

“It’s important to recognize that

you will never be the expert”

Reshaping Teamwork:
Building & Scaling Products
with Distributed Teams

San Francisco
June 20

Here at Miro, we are working on a visual workspace for innovation where teams manage projects, design products, and build the future together.  We are always interested in the ways leading organizations are dealing with these issues, and we hope to gather the best insights for our customers. That’s why we are excited to announce our first meetup in San Francisco dedicated to challenges of building a product in a distributed team. We are also proud to share our intеrview with one of our speakers, Upwork’s VP of Product Management, Jessica Tiwari.

What is your background? How did it bring you to the current point of your career?

I went to school to be a French horn performance major. It’s classical musician training, which is weird in the product industry, but also very appropriate for Upwork because it’s basically like old-school freelancing. So it was a fascinating perspective to develop about what it feels like to be auditioning for your next gig all the time.

I’ve been at Upwork for six years. Prior to that I was in product at an enterprise company that exclusively dealt with project-faced everything: project-faced tracking, project-faced expenses, project-faced performance, project-faced research planning, CRM, you name it. And that has been a very useful perspective, because that’s how freelancers run their lives. That’s how they manage their time and evaluate how they’re going to be successful in the long run.

Can you please describe your role at the company?

At Upwork I’m responsible for two company imperatives: the domestic imperative and the small-business imperative. If you look at what Upwork has done successfully since we started, we’ve been very good at convincing startups, entrepreneurs and sort of risk-tolerant individuals to hire remote freelancers. These are early adopters who are willing to try anything.

With the domestic imperative, what we’re trying to do is attract the more established businesses, maybe more conservative, and get them to test our freelancing. Maybe they’ve never hired remote workers before, maybe not even as employees. They’re not going to start by hiring a freelancer far away, so we’re trying to get them more comfortable with the concept by introducing them to using domestic freelancers.

The small-business imperative is very similar. It’s about trying to shift Upwork from being a place where one user comes to get a single project done to more like a business tool and business partner for established small and medium-sized businesses.

What lessons have you learned over the course of your career as a product manager?

I think the most important one is to recognize that you will never be the expert. And that if you’re at a place where you feel the discomfort of not knowing exactly what you are doing, it means you are learning the fastest. And that’s been a hard thing for me to learn, but I think that growth mindset has been incredibly important, especially as I have advanced in my career. I think there’s this false illusion that once you get to a certain point, it’s because you know everything. That’s completely not true.

Can you describe your team and the main tasks and problems that you’re dealing with day to day?

I spend most of my time coordinating the work that the whole company is doing around these tasks. I’m focused on defining product building. Are we solving the right problems? Are we building the right product? Are we doing it in the right way? And also, how do the marketing efforts accelerate and support what we’re doing in product? And how are operations able to help us tackle the problem that we’re trying to solve? So I spend most of my time aligning all of the different organizations within the company on the common problem and having us all work together to try to solve it.

What are the main challenges you face and how do you approach them?

The biggest challenge that we have is that we’re fully distributed. It’s not the type of remote where you have one collocated bunch of people and then another collocated bunch of people. We have individuals all over the world working together. And things change fast. Our strategy is changing quickly. So when you’re trying to figure out an efficient way of communicating with individuals all over the world so that everyone can understand, it’s really challenging.

To address this problem, one thing that I found to be incredibly important is to have everything written down. The first thing that you lose when you start to have remote team members is the ability to keep someone up to date just by chatting with them. Especially when you’re working with people with different levels of English. You can’t rely on everyone’s understanding of what you said to be the same. So you need the ability for people to go back and comment on a document to make sure that everyone understands.

What’s your “secret sauce” for delivering innovative products, services and customer experiences?

One of the things that’s really driven our success is that we rely on Upwork freelancers to build the product with us. Those freelancers are so invested in what we do, why we do it and how it can benefit their community. That’s one of the challenging things that you have with a remote team: to create that culture and sense of “what I do is important.” We get a lot of that for free because we are using our own platform to help build our product. Everyone immediately understands why what they do matters and how important it is, without having to sell it to them.

What advice can you give to aspiring product managers?

Make sure that you always leave enough time to focus on understanding the problem you’re trying to solve. Is it a real problem? Is it worth solving? What happens when you do? Now that I have been at this long enough, I am spending a decent amount of time unraveling my own solutions to problems that didn’t matter. It would be great to skip that part.

What are your top three tools for remote collaboration?

It doesn’t need to be a specific tool. We are really heavy G Suite users, and I don’t know how I would do my job without it. Since so much of our alignment and collaboration happens asynchronously, that ability to see who’s read it, what they commented, how they edited it is super important. So that’s a really basic tool, but I think it’s incredibly important. And then whatever chat tool you have. It could be Slack, Skype for Business, or we use our own proprietary tool. Real-time communication is incredibly important, so you have to have something.

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