How Insperity Unlocked Faster Deals and AI Insights with the IAM Platform

In 1986, two entrepreneurs with a legal pad sketched out a solution to a problem they knew well: How can we free business owners from the administrative drag of HR so they can focus on what matters?

That sketch became Insperity, now a $6.6 billion HR services leader supporting over 100,000 businesses and millions of employees.

Managing that scale requires powerful tech to keep agreements moving as fast as the business. Two key tools in Insperity’s stack: Salesforce and Docusign.

What began with an eSignature deployment in sales has since evolved into an Intelligent Agreement Management platform powering workflows across sales, legal, marketing, IT, and procurement.

How can you speed deals when your sales force is everywhere?

Steady growth took Insperity from a single office in Texas to dozens nationwide, but its sales process didn’t keep pace.

Reps scattered across the country still sent agreements by email or even snail mail, adding costs, risk, and time to every deal.

“When you’re dealing with paper and postage, things can get lost and you have to repeat the process,” said Tosh Harris-Hogues, product manager in IT product innovation. “We started thinking about how we could simplify this for everyone involved, and that’s what led us to Docusign.”

Docusign eSignature replaced pen, paper, and postage with a faster, trackable way to send and sign agreements, marking a turning point for the business.

“It’s made a phenomenal difference in the way we service our clients,” said Harris-Hogues.

Connecting Docusign + Salesforce slashed cycle time from weeks to days

Freeing signing from its paper-based roots was just the beginning.

The real breakthrough came when Insperity automated agreement generation in Salesforce using Docusign Gen. With just a few clicks, reps can generate personalized proposals, NDAs, project scopes, and master service agreements right in the platform they use to manage deals.

Instead of starting from scratch, they launch templates that automatically pull in Salesforce data and adjust terms based on deal details.

“By connecting Docusign and Salesforce, we were able to streamline the agreement process from the time we first talked to a prospect to the point of onboarding,” said Harris-Hogues.

The integration also gave sales leaders a clear view of the pipeline, making it easier to spot slowdowns and keep deals on track.

What started in sales sparked a company-wide transformation

Building on early momentum with Docusign Gen, Insperity rolled out CLM to support more complex workflows across legal, IT procurement, and marketing.

While Gen streamlined document generation, CLM brought structure to everything that follows: reviews, approvals, and staying on top of obligations after the signature.

By centralizing management on a single platform, Insperity gained tighter control and a single source of truth for current and legacy agreements.

Docusign Iris brings intelligence before and after the signature

With all agreements flowing through the Intelligent Agreement Management platform, Insperity’s legal team is unlocking the AI features powered by Docusign Iris.

Before signature, Iris analyzes third-party agreements, flagging risky clauses that deviate from Insperity’s policies to support faster reviews and approvals.

After signature, the AI extracts key terms and metadata—such as renewal dates and payment obligations—and makes them easy to search and act on.

Looking ahead, Harris-Hogues plans to use AI for a project focused on centralizing and streamlining Insperity’s procurement agreements.

“I am truly excited about what we’ll be able to do with Docusign Iris,” she said.