If you’ve ever felt frustrated by how slow or messy agreement work can get, you’re in good company. 

Insperity, an HR services company with teams spread across the U.S., ran into the same issues. Sales reps were emailing agreements, legal reviews dragged on, and key dates were buried in PDFs.

So they set out to fix it. Here’s the playbook they followed, with takeaways you can put into action today.

Step 1: Stop recreating agreements from scratch

• The problem: Reps wasted hours drafting proposals, scopes, and NDAs manually.

• What Insperity did: They connected Docusign Gen with Salesforce so reps could generate pre-filled agreements directly from deal data.

• What you can try: Look at your most common agreement type. Could you set up a reusable template that pulls in fields from your CRM or system of record? Start with one template and build from there.

Step 2: Get real-time pipeline visibility

• The problem: Leaders couldn’t easily see where deals were stalling.

• What Insperity did: Integrating Docusign with Salesforce gave them end-to-end visibility into agreements, helping them spot slowdowns and keep deals moving.

• What you can try: If you already connect Docusign to a CRM, make sure leaders know how to pull agreement data into their pipeline views. Even simple reporting can reveal bottlenecks.

Step 3: Bring order to complex reviews and approvals

• The problem: Legal, IT, and procurement reviews crawled along over email.

• What Insperity did: They rolled out Docusign CLM to route documents automatically, set approval paths, and track obligations.

• What you can try: Identify the agreement type that stalls most often. Could automated routing or pre-set approval paths reduce the back-and-forth?

Step 4: Centralize agreements into a single source of truth

• The problem: Current and legacy agreements were scattered across teams and systems

• What Insperity did: They used CLM to consolidate agreements into one searchable hub, giving them tighter control.

• What you can try: If agreements are spread across drives, inboxes, or shared folders, start by pulling one category (like vendor contracts) into a central repository.

Step 5: Use AI before signature to catch risks

• The problem: Risky clauses in third-party contracts slowed down legal reviews.

• What Insperity did: With Docusign Iris, they used AI to analyze contracts and flag clauses that didn’t align with company policy.

• What you can try: Even if you’re not using Iris yet, create a checklist of your top three “red flag” clauses so reviewers can catch them faster.

Step 6: Use AI after signature to track obligations

• The problem: Renewal dates and payment terms were buried in PDFs and easy to miss.

• What Insperity did: Iris extracts key metadata, like renewal dates and payment obligations, so they’re easy to search and act on.

• What you can try: Start by tracking renewal dates in a shared calendar or spreadsheet. Building that habit now makes it easier to automate later.

✅ Your move: If you have questions about any of these steps and how you might apply it to what you do, add your thoughts or questions in the comments section below 👇