What Makes Upwork a Fulfilling Place to Be a Salesperson?

The culture, company growth and its mission, said reps.

Written by Alton Zenon III
Published on May. 07, 2021
What Makes Upwork a Fulfilling Place to Be a Salesperson?
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It’s difficult to sell a product you don’t believe in. It’s also tough to fully immerse yourself in a business that isn’t growing or doesn’t provide many opportunities for individual growth. 

Salespeople at Upwork said they don’t have this problem. 

“It can be tough when you’re not selling things that have a higher purpose in the world,” Marketplace Account Manager Nikki Thayyil said. “But that’s not the case at Upwork. I see how my work impacts businesses and people’s lives. And that work means so much more now than when I started because of our growth.” 

Thayyil said she joined the work marketplace three days before its initial public offering in October 2018. The platform — through which over $2 billion worth of work is done annually — has been growing steadily since. According to the company president and CEO Hayden Brown, 2020’s shift to remote work fueled that growth even further. 

In a press release, Brown said that 2020 was a “watershed year” for Upwork because many companies embraced remote work and freelance talent. The company’s revenue for 2020 grew by 24 percent to $373.6 million, over $100 million more than annual revenue in 2018 and $73 million more than in 2019.

As Upwork grows, salespeople say they grow along with it.

We’re all here to help each other get to the next level.”

Thayyil, as well as Regional Sales Manager Meric Bissell and Enterprise Account Manager Sara-Ann George, have been promoted at least twice since they joined around three years ago. George said that while sales is inherently competitive, Upwork’s sales culture is rooted in peer-to-peer support. Team members lift one another by knowledge-sharing, and shunning an “every rep for themself” mentality.

“Our culture is not just upleveling our individual careers but seeing each other do better,” George said. “We’re all here to help each other get to the next level.”

Bissell — who has experienced five upward title changes in four years — said Upwork’s leadership team also facilitates this growth culture because they empower salespeople to take on new challenges. He said he took a non-traditional career path at the company and was worried about his readiness for certain roles, but his managers motivated him to take the leap. 

“At each new step in my career here, I was worried about whether I could perform in these new roles,” Bissell said. “But our leaders recognize our talents and build up our confidence so we can succeed and contribute to a winning team.”

Bissell, George and Thayyil agree that Upwork’s mission-driven growth, paired with its supportive culture and room for upward mobility, make the company a fulfilling place to be a salesperson. 


Upwork team
Upwork sales team

What’s energizing about being a salesperson at Upwork amid all its growth?

George: We’re on the ground floor of this revolution of work. We were doing well when I started in 2017 and there were some case studies on the effectiveness of remote work, but it wasn’t as widespread. Now that we’re all working remotely, the chickens are home to roost and we have to be agile. So as a salesperson, it’s a unique opportunity to be powering that. 

Bissell: With all our growth, it’s fulfilling being on the sales team because of how important we are to the organization and its goals. Every sales function is critical to Upwork’s success and we can stand out as individuals contributing to the company’s goals. We see our work reflected in our earnings calls and stock price. Our sales team is at the forefront of Upwork’s growth and it’s exciting to be part of that. 

Every sales function is critical to Upwork’s success.”


Thayyil: We went public on my third day and now I’m seeing more clients understand our value and I’m helping with their business strategies. We’re seeing so much growth in our marketplace, which is essentially what I came to Upwork for. And 20 years from now, I’ll be proud of the work I’ve done here.


What has your professional growth looked like since you joined Upwork’s sales team

George: When I wanted a promotion, naturally, I spoke to HR and leadership. But where Upwork takes things further is I can identify my gaps in the skills necessary for a new role then go to different members of the team to fill them. If someone is good at discovery or presenting, I can ask them for a hand. And we hire those helpful people that say, “Let me help you and pull you up.” Our culture is not just upleveling our individual careers but seeing each other do better. Everyone is busy but nobody is too busy to help. 

Everyone is busy but nobody is too busy to help.”


Bissell: I started in an entry-level position on the business development team and I was originally trekking the individual contributor route. But I had a great boss and I spoke to him about my interest in a leadership role. So I took my first management position on that team piloting a new way of going to market for account executives. Then I moved to a sales manager role on the mid-market and enterprise AE team. 

My career path wasn’t traditional but it shows how many paths there are at Upwork. There are essentially unlimited opportunities for people to move in the org and change what they can do. 

Thayyil: We also have conversations on a day-to-day basis on topics and with people that are so diverse, which is very stimulating. Since we are not siloed to a specific industry, we have to know how to speak to everyone and anyone because of the variety. It creates an environment where we’re constantly learning by talking to people across different businesses and that makes the work exciting because you don’t know what’s going to come each day.


upwork sales

What is Upwork’s collaborative culture like?

Bissell: Collaboration is very important for us. By putting our heads together, we can get a greater result than we would by operating independently. We’re set up so that one person succeeding doesn’t come at the expense of someone else. This idea is combined with a transparent culture, which allows us to talk about things that aren’t going well. Then we can leverage our different backgrounds and expertise to find a solution. 

Thayyil: The team has a think-tank vibe and our managers are specific about having diverse teams. Upwork has made that a critical goal and core value of our company and I’ve seen the success of it. Diversity breeds success and you can see everyone’s unique perspectives ripple throughout the team.


Upwork sales team

How does leadership contribute to people’s growth and the team’s overall culture?

George: Upwork cares about its employees and a lot of that is driven by our executive leadership team and our CEO. Last year when I was in the dumps, my manager sent me a care package and told me to take time to rest. Many of my peers in leadership speak about how they uplift their team to be successful. 

As an individual contributor, it’s motivating that leadership cares about my well-being, not just revenue or my quota. That empathy impacts my performance and pushes me to try harder. I feel the leaders on my team and at the executive level rally around me and push me to my best.

Leadership cares about my well being, not just revenue or my quota.”


Thayyil: Managers have goals to promote people in their teams. So they care not only about my contributions to the team, but also how that work is benefiting my career and professional development. I can go to bat for myself when I want to take advantage of an opportunity. We’re also encouraged to extend that mentality to new people coming to Upwork. 

The company also puts money on the table to help us on our individual journeys with a learning and development budget, interview prep courses and mentorship programs. 


What’s the most fulfilling part of being a sales rep at Upwork?

George: I feel like Upwork provides quality of work to end clients and quality of life and professional experience to employees.

Thayyil: For me, it’s the mission: creating economic opportunity so people can have better lives. It means a lot to know that my work provides so much value to other people in such a hectic time. And this idea has helped keep me sane during a period of so much uncertainty. 

Bissell: The mission is the reason I joined the company and I believe we can be a massive business one day because of it. Being part of that mission, and having our voices heard in helping the company grow, makes me excited to go to work every day.


Responses have been edited for length and clarity. Photos via Upwork.

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