How Woodruff Sawyer Tackled a Brand Overhaul with a Leading Design Agency on Upwork

Woodruff Sawyer has been insuring client innovation for over 100 years—but lately, it’s gone through some innovation of its own.

When the Bay Area-based corporate insurance firm’s marketing team needed to shift its focus from sales support to a bigger branding initiative, there was suddenly way more creative work to be done—more than they could handle on their own.

That’s when VP of Marketing & Sales Operations, Jeff Fenigstein, turned to Upwork, which he’d been using in other capacities for close to ten years. The team started small, learned the ropes, and today has expanded to create their own in-house creative marketing studio with remote talent and agencies who are helping them shape the future of their brand. Here’s their story.

Upping design bandwidth with flexible talent

The demand for design talent was a constant for departments across Woodruff Sawyer, and this kept the core marketing team busy. “We’re in commercial insurance, so we’re always looking for ways to not just make the data look better, but to make it more understandable.” The team started small, engaging remote talent for design, video production, writing, email, and translation projects.

“We use Upwork primarily in the marketing department, but there are projects outside of marketing that require design and we’ve helped those teams to use Upwork, and created a pool of designers that they can work with for their needs.”

It made a big difference. The additional bandwidth and extended team of trusted freelance designers who required little to no hand-holding meant the core team could focus on more critical projects. “Even projects that aren’t marketing-related need to be on-brand, and they need to be professional,” Fenigstein says. Whether they were creating emails in a marketing automation program or publishing blog posts to WordPress, it could all be done with very little direction.

And where the budget was concerned, flexible talent provided a more affordable way to grow resources when and how they needed without the big financial commitment. It was exactly the flexible, scalable solution the team needed.

Leveling up to pull off a major rebrand

When it came time for the company to undertake a major rebrand, Fenigstein knew it was time to ramp things up.

“Before I joined Woodruff Sawyer, my team was focused mainly on sales support. My job was to grow the brand, grow awareness, and generate leads. That’s a tall order,” Fenigstein says. The first step was a complete rebrand. That included updating thousands of assets: all of the sales collateral, messaging, and an entirely new website, which required more help and coordination.

“I had a marketing team of about two people and one senior designer. There was no way we were getting [a rebrand] done in-house, and forget about doing anything else. We wouldn’t even be able to handle that.”

To keep the project contained and turnkey, Fenigstein turned to an agency on Upwork. “We needed to level up, and needed people who are not only competent but can run a project and also interpret our brand. They see the bigger picture of the world that their project is in. And we needed to make sure who we engaged had capacity when we needed it. We work with individual freelancers too, but it’s a bit more management on our part.”

Fenigstein came across Richmond Concept, a leading design agency on Upwork. The agency provides both the diversity of skills they need and a convenient, single point of contact for Fenigstein’s team. “It’s been really helpful for us to work with an agency on Upwork. The people on my team can send them a variety of projects requiring various skill sets, and the built-in coordination means that it doesn’t have to be a lot of individual conversations.”

Building a better brand and stronger partnerships

The rebrand was a total success, and Woodruff Sawyer has since retained the Richmond Concept team as a design consultancy to carry out more conceptual projects and strategies.

“Now, we have a partner that understands us and our brand and they can scale to support us because they have the experience and expertise. Today, we find ourselves with not only new branding but a more sophisticated identity that helps us connect with the partners we want.”

For Woodruff Sawyer, remote talent and agencies aren’t just a temporary solution—they’re key to their future as a brand. Fenigstein says, “I think marketing leaders need to work with online talent because marketing encompasses so many areas—design, content, technology, analytics, research—and your team will never have all the specialized expertise that you want. Even if your team is really strong in all areas right now, things change quickly. Building an online talent pool really is the best way to have the different specialties that you always wanted to have.”