It is a well-worn adage that change is the only constant in life. But it remains true! This is especially so in the world of product, where the digital transformation of the past 2 years has caused a massive adoption of digital tools in all areas of the market, from the largest corporation down to the individual freelancer making a career remotely. Few companies are as plugged in to that transformation as Upwork, “the world’s work marketplace.” In this conversation, Upwork Chief Product and Experience Officer Samuel Bright talks about how he leads his product teams to successfully navigate that transformation. It starts, he says, with a culture of making the customer win big. 

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On PEX principles

Samuel Bright joined Upwork in November 2020 to lead the product and experience team. He calls this team “PEX.” It oversees all customer touch points. This wide ranging role includes product, design, research, and writing, and more. These include trust and safety, talent, success, community business development, new businesses risk and payments, customer support, and international expansion. Bright highlights the “flywheels of customer insights coming in, and informing how we build products and deliver them into the market, generating more customer insights and response and then going from there.”

Bright has overseen Upwork’s transition from a single product line company to a multi-product line company. The key to that transition, he says, has been in establishing core principles. Teams can rally around these to inform the thousands of micro decisions that they make every day to all be headed in the same direction. The number one principle? Make the customer win big.

Bright says “it starts with culture and embedding that in how you operate. The idea that customer delight needs to be at every touchpoint. When we were writing our team charter, we established what we called PEX [product and experience team] principles. And there were four of them: Make the customer win big, lead with quality, build for scale, and go further together. And those are sort of like the cultural touchstones that we have sought to align around. 


“When we are recognizing team members for promotions, or in various forums, we give out quarterly PEXcellence awards. These are for people who have demonstrated excellence around living each of those values. They then ladder up to the corporate values. 

“And so I start with ‘make the customer win big’ because it’s not just a product concern; it impacts every function, every team, and every decision across an organization. It’s about helping us think and act customer-first. Then, especially in product led organizations, the broader organization is able to organically absorb, embrace, and reflect that philosophy. 

“That has guided us as we’ve been going along this journey from being a single product line company to being a multi product line company, where we’ve launched a series of different product lines, recognizing that needs have evolved in the middle of this like work awakening.”

On adding value to team member careers

Bright says principles and specifically a product vision cause clarity in building products. It also helps in attracting and retaining team members. Building and communicating a product vision and PEX principles, and connections to roadmap and metrics, empowers team members. Beyond that, Bright also wants to set up team members for success throughout their whole careers, not just during their time at Upwork. So an important goal is to add value to team members throughout their time with the company.

He says, “another key element is to really think about the long arc of careers. I really seek to develop folks at Upwork. And not just for their tenure here, but also for where they want to be 10 years from now. Because I’ve seen people grow. I’ve seen people leave. I’ve seen people leave and come back. I’ve seen multiple rounds of boomerangs at different points in time. 

Develop talent

As managers, one of the most precious gifts that our team members entrust to us is their careers. It’s never an ownership. It is a lease. We are borrowing it for a very specific period of time. And the question is, are we adding value in that moment? And so to the extent that that philosophy is key, as we’re hiring talent, that has a lot of value. I want people to think about and feel like that sense of enrollment, pride, ownership. Like, I was part of Upwork PEX from 2020 through x period of time. They know that that commands a premium, not only for the career, but also in the market overall. So I think about that, as we’re hiring talent more broadly. 

“And as I’m hiring folks, specifically for my leadership team, you know – you hire senior people to tell you what to do. So that’s why I’m constantly seeking folks who have strong POVs, who are opinionated, who are data driven, and are really looking to have leadership impact beyond their functional area, but really treat their position on PEX staff as being part of a round table that helps to guide the overall organization, bringing their unique perspectives and brilliance to bear.”

On what makes a great product

PEX is built around a customer-first approach and the guiding principle of making the customer win big. Thus it is not surprising to hear that Bright believes great products are defined by what the customer wants. He says great products are “defined by the customer, not by the team creating it. The customer decides whether or not a product is great.”

Bright continues, “what I will say is that really great products, they’re not only listening to customer pain, but they’re sort of like X-rays. They see pain that the customer isn’t even able to see yet, and isn’t even able to give voice to, and they solve that pain proactively. The customer is delighted before they even knew that they needed to be delighted, or that there was a path for them to be delighted in that particular way. It’s tricky, right? Because sometimes I think that can be used to justify just building something without there being a customer need for it. But if there’s a really deep understanding of what the customer is solving for, then there’s a way to get ahead of where there might be pain points in ways that will delight them.”

About the speaker
Samuel Bright Upwork, Chief Product and Experience Officer Member
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