Vestwell Turns Deals Into Revenue 93% Faster with Docusign and Salesforce

“Most people don't really think of the financial services industry as human-centric,” said Jon Mark, chief operating officer at Vestwell. "But at the end of the day, money is what enables all of us to realize our dreams—whether that means saving for retirement or a child’s college.”

When Vestwell launched nearly a decade ago, it set out to make those dreams accessible to the small businesses that legacy systems had left behind. Today, the New York-based fintech powers retirement savings for 1.6 million Americans, a figure growing each month.

Many of the businesses Vestwell serves had never offered a workplace savings plan before. For most, it’s their first retirement and workplace savings benefit for employees.

But as Vestwell’s reach expanded, the agreements that powered signing up new clients became a bottleneck to its mission and its bottom line. With Docusign, the company built a foundation that could grow with it—cutting onboarding time by 93% and helping more than 1,000 new businesses each month make saving easier for their people.

Getting complex agreements out the door in minutes instead of hours

Retirement plans aren’t one-size-fits-all. Small businesses offering their first 401(k) have different needs than financial institutions managing multiple plans. Every detail—from employer contribution amounts to who can participate in the plan—has to be captured correctly in the agreements that make those plans official.

Creating agreement packages used to be painstaking work. Sales and ops teams had to select the right configuration, manually re-enter client details already stored elsewhere, and remove or add sections based on plan design or the investments being offered in the plan. All of that work fell to revenue-producing teams. 

“It was taking an hour and 15 minutes to get an agreement package out the door,” said Mark. “That just wasn’t going to work for where we needed to go.”

To remove friction, Vestwell connected the Docusign Intelligent Agreement Management platform with Salesforce, bringing data, documents, and decisions into one seamless flow. Sales teams now kick off agreements directly in their CRM, and Docusign CLM automatically assembles, routes, and tracks everything to completion.

The result: What used to take 75 minutes now takes five. Errors from manual edits or outdated templates have virtually disappeared. And by embedding down payments directly into the signing experience through Docusign's Stripe integration, Vestwell reduced post-signature drop-offs by 70%.

Meeting customers where they are 

In his five years at Vestwell, Mark has seen the company's go-to-market approach evolve from a single strategy to one that adapts to each client.

Today, some clients move through a fully self-service experience, configuring their plan and signing agreements without ever talking to a salesperson. Others prefer a human touch to design complex or custom plans. The same Salesforce–Docusign backbone powers both.

“When we first launched Docusign, we were saving 200 hours a month with only a couple hundred clients," he said. “Now, with over a thousand new clients a month, we’re in a spot where if we hadn’t put this solution in place, I don’t know if we could have scaled the way we have.”

Evolving with AI—without losing the human element

The Docusign integration unlocked an unexpected benefit: better customer service. Once Vestwell streamlined how new clients came on board, it focused on helping them get the right answers faster with a generative AI chatbot. Then, the team enhanced the bot by connecting it to agreement data captured through Docusign and stored in Vestwell's platform. 

Now, when someone asks, “When can I  start saving?” or “How much does my employer match?" the chatbot can provide a more personal response based on their actual plan details.

“Customers come to Vestwell when they want a modern experience, and we're so excited to be able to deliver it to them,” said Mark.

A clear path forward

Mark expects AI to change how customers interact with financial services. But some fundamentals won't change. “We're still going to need people to agree to a set of terms at the end of the day,” he said.

Docusign helps keep it simple, secure, and adaptable. Vestwell continues to refine its systems to make saving simpler for everyone. The company is exploring new Docusign capabilities, including AI-assisted tools and embedded signing, to help teams move faster behind the scenes and give clients an even smoother experience up front.