Weekly stalled deal nudge for ConnectWise PSA via Gmail

Every Monday at 8am in my local timezone, find stalled sales opportunities in ConnectWise PSA, send each buyer a gentle nudge from my Gmail, and log the outreach back into ConnectWise as a CRM activity so the assigned rep has a clean record.

Step 1: Pull stalled opportunities from ConnectWise PSA. Use List Opportunities to fetch opportunities that are still active, meaning the stage name is not Won, not Lost, and not Closed, and whose lastUpdated date is older than 14 days from today. Page through all results.

Step 2: For each stalled opportunity, look up the buyer. Call Get Company using the opportunity's company id to get the customer's company name, and call Get Contact using the opportunity's primary contact id to get the contact's first name, last name, and email address. If the contact has no email address on file, skip this opportunity and move on.

Step 3: Skip anything we already touched. Call List Activities filtered to this opportunity and only proceed if there is no activity logged against the opportunity within the last 7 days. If a recent activity already exists, skip and move on.

Step 4: Draft a short, warm follow-up email, three or four sentences, addressed to the contact by first name. Reference the opportunity name, the customer's company, and the last known stage in plain language. End with a soft open question that invites them to restart the conversation, for example asking whether anything has changed on their side or if there is a better person to loop in. Keep the tone friendly and human, not pushy.

Step 5: Send the email through Gmail using Send a Message. The To address is the primary contact's email, and the Cc address is the assigned sales rep's email from the opportunity. Use a subject line that references the opportunity name, for example 'Quick check-in on {opportunity name}'.

Step 6: Log the outreach back in ConnectWise. Call Create Activity to create a new CRM activity tied to the opportunity (and to the same company and contact). Set the activity name to 'Follow-up email' and put the subject and body of the email we just sent into the activity's notes so the rep can see exactly what went out when they open the timeline.

When the run finishes, return a short summary I can read at a glance: how many opportunities I had open, how many we emailed, how many we skipped, and the reason for each skip (no contact email, or recent activity already on file).

Additional information

What does this prompt do?

Pulls open opportunities from ConnectWise PSA that have not been updated in the last two weeks.
Drafts a short, personalized follow-up email referencing the deal, the buyer's company, and the last known stage.
Sends the email from your Gmail to the primary contact, with the assigned sales rep on cc.
Logs a Follow-up email activity back on the opportunity so the rep has a clean record in ConnectWise.
Skips deals with no contact email and deals that already had outreach in the last week.

What do I need to use this?

A ConnectWise PSA (Manage) account with permission to read opportunities, companies, contacts, and activities, and to create activities.
A Gmail account that can send messages on your behalf.
Your sales pipeline configured with stage names so we know which deals count as open versus Won, Lost, or Closed.

How can I customize it?

Change the schedule from Monday at 8am to whatever cadence matches your sales rhythm.
Tune what counts as stalled, for example 10 days instead of 14, or skip deals that had outreach in the last 5 days instead of 7.
Adjust the tone and length of the email, or have it ask a specific question tied to the deal's stage.

Frequently asked questions

Will this email my buyers without me reviewing it first?

By default yes, it sends each follow-up automatically every Monday. If you would rather review first, you can ask the workflow author to switch it into a draft mode so the messages land in your Gmail drafts for approval before sending.

How does it know a deal is stalled?

It looks at every opportunity in an active stage (anything that is not Won, Lost, or Closed) and picks the ones whose last update in ConnectWise is older than 14 days. You can change that window to match how your team defines a stalled deal.

What if the opportunity has no contact email on file?

It quietly skips that deal so you do not get errors. The rep can fill in the contact's email in ConnectWise and the next run will pick it up.

Will my rep know the email went out?

Yes. The email is cc'd to the assigned sales rep, and the workflow also writes a Follow-up email activity onto the opportunity in ConnectWise so it shows up on the rep's CRM timeline.

Can I send from a shared sales inbox instead of my personal Gmail?

Yes, connect the Gmail account you want the messages to come from. Any Gmail or Google Workspace mailbox you can sign into will work.