How Tess Trotter Built a Digital Marketing Agency on Upwork

When Tess Trotter signed up for Upwork in 2016 as a solo freelancer, she had a clear set of values and a vision for her career. Today she leads CEP Communications, a six-person, all-women digital marketing agency serving some of the world's most recognized consumer brands. Here’s how Upwork helped her build her career and her company.

A freelancer with a purpose

Right out of college, Tess knew the traditional office environment wasn’t the right fit. She wanted a career built around her values: flexibility, autonomy, and the freedom to do meaningful work on her own terms. She started freelancing in 2016, initially sourcing work from Craigslist and Indeed before discovering Upwork.

The shift was immediate. Upwork's infrastructure gave her direct access to quality clients, a transparent system for building her reputation, and a reliable pipeline for new business. Other platforms could get her work, but Upwork could get her somewhere in her career.

She focused on delivering results, let her reviews show her quality of work, and watched her client roster grow. One strong engagement led to another, and referrals started coming in. What began as a search for flexible, meaningful work was becoming something more substantial.

"Upwork has been my primary lead source for the past 10 years," Tess said.

Her agency specializes in social media management, digital advertising, email marketing, SEO, branding, and web design. Through Upwork, she’s worked with globally recognized clients including Indeed, Ralph Lauren Fragrances, and Land O'Lakes, while building a reputation for cost-effective, results-driven services that move the needle on brand awareness and lead generation. For Tess, the Upwork platform was never just a marketplace, it was the foundation her business was built on.

Scaling from solo to agency

For the first few years, Tess ran CEP Communications on her own. She was selective about clients, disciplined about delivery, and intentional about the kind of agency she wanted to build. Upwork's built-in tools made it possible to manage that growth without the overhead of traditional business development.

When COVID-19 shifted business online in 2020, demand for Tess's services surged. Brands that had resisted digital marketing no longer had a choice, and they needed help fast. Tess was ready. She made her first hire that year and began building her team in earnest.

Upwork was central to that process too. Two of her current team members were sourced through the platform and have been with her for over five years. The same tools that helped her find clients helped her find talent. Upwork's candidate profiles, work histories, and reviews gave her a clear picture of who she was hiring before any contract was signed.

"I wanted to foster a flexible, nurturing environment, especially for the mothers on my team," Tess said.

That vision shaped every hire she made. CEP Communications is entirely female-led and female-employed, with a remote structure that gives every team member the flexibility to do their best work. As the business grew, Tess also pursued women-owned and minority-owned business certifications. Those credentials opened doors to new clients and strategic partnerships and deepened her connection to a network of like-minded female business owners who share her values.

The agency Tess leads today looks very different from where she started. But the core has stayed the same, centered around quality work, long-term relationships, and a team built to last.

Why Upwork became her competitive advantage

For Tess, Upwork's value goes well beyond lead generation. The platform's built-in tools have become core to how she runs her business day to day.

Client reviews give her a reliable way to vet prospective clients before engaging. She can see how a client has treated previous contractors, what they typically pay, and what kind of projects they bring. That transparency cuts through a lot of uncertainty and helps her commit to the right engagements, rather than simply the available ones.

Streamlined proposal submission keeps her pipeline moving without the overhead of a dedicated sales function. And Upwork's consultation feature has proven to be one of her most powerful growth levers. Consultations consistently convert into ongoing management clients, generating a steady stream of new business with minimal additional effort.

"I wouldn’t be where I am today without Upwork," she said. "Upwork doesn't just give me clients. The direct client feedback allows me to continuously improve, and the steady demand I receive for my services on Upwork gives me the ability to reinvest in hiring, training, and infrastructure."

The cost efficiency stands out too. Her Connect spend runs significantly lower than comparable campaigns on Google Ads, freeing up the budget that she channels back into her team and the quality of work they deliver. For a founder who has always prioritized building sustainably over scaling fast, that kind of leverage matters.

Tess also runs a strict onboarding process for new clients. She takes at least a week up front to gather branding materials, complete her research, and align on deliverables and timelines. That discipline, combined with Upwork's infrastructure for communication and payment, means fewer surprises on both sides and stronger partnerships over time.

Freedom by design

Ten years in, Tess's definition of success looks a lot like the life she set out to build when she first left the traditional workforce.

She takes extended trips of three to four weeks each year while her team keeps operations running smoothly. She listens to her body, takes breaks when she needs them, and prioritizes her health and family without apology. She runs a business that reflects her values at every level, from the clients she takes on to the culture she’s built internally. That kind of freedom didn’t happen on its own. It was built deliberately, project by project and hire by hire, with Upwork as the foundation.

"Upwork has given me the ability to live life on my own terms," she said. "That freedom has improved my overall quality of life in ways I never imagined possible."

There’s something worth noting in that statement. Tess isn’t describing a lucky outcome. She’s describing a strategy. She made deliberate choices about the platform she committed to, the team she built, the culture she protected, and the clients she served. Upwork gave her the infrastructure. She did the work.

Tess started with a laptop, a clear sense of purpose, and a platform willing to meet her there. What she built from that starting point is a testament to what’s possible when talent finds the right tools and refuses to settle for less than the career it deserves.

If you’re interested in working with Tess or her agency, you can visit her profile or the CEP Communications agency page on Upwork.

"[Upwork has] been crucial to my substantial growth, both as a business owner and an individual."