If you’ve got renewals, expansion, or upsell targets (and who doesn’t these days?), you know you can’t just wing it. Your CSMs are already swamped. You need to make upselling and cross-selling a repeatable part of how your team works, not just something that happens if someone remembers. Enter Planhat—a customer platform with the kind of automation that can actually save you time, not just create busywork.
This guide is for anyone who needs to build automated playbooks for upselling and cross-selling in Planhat—without getting lost in the weeds or chasing shiny features that sound great but don’t move the needle.
Why Automated Playbooks Matter (and Where They Fall Short)
Let’s get this out of the way: automation isn’t magic. If your team doesn’t have a clear process, automating it just means you’ll make the same mistakes faster. But if you know what triggers an upsell or what signals a customer might be ready for more, Planhat can help you turn that into an actual, repeatable workflow—so you don’t have to rely on someone’s memory or endless Slack reminders.
What works:
- Automating clear, repeatable triggers (like “customer hits usage threshold”).
- Standardizing outreach (so nobody forgets to follow up).
- Tracking outcomes, so you know what’s working and what’s just noise.
What to skip:
- Overly complex branches and edge cases—keep it simple.
- Automating things that really need a human touch (like delicate price conversations).
- Playbooks that turn into a wall of notifications nobody reads.
Step 1: Get Your Data in Shape (Don’t Skip This)
Before you start building playbooks, stop and check: do you actually have the data you need to trigger them? Most failed automations come down to garbage in, garbage out.
Key things to check: - Product usage data: Are you tracking key metrics (logins, seats, usage, etc.) in Planhat? - Contract details: Is your renewal/upgrade info up to date? - Customer health: Can you spot healthy accounts vs. at-risk ones? - Lifecycle stage: Do you know who’s new, who’s mid-contract, who’s up for renewal?
Pro tip:
If you’re missing this stuff, don’t try to automate upsells yet. You’ll just annoy customers with irrelevant outreach.
Step 2: Define What Triggers an Upsell or Cross-Sell
This sounds obvious, but most teams skip it. Don’t just say “when a customer is happy.” Get specific.
Common triggers that actually work: - Customer hits a usage cap (e.g., storage, seats, API calls) - Consistently high product engagement - New feature released that’s not in their current plan - Renewal window approaching (good time to bundle an upgrade) - Customer requests something outside their current contract
What doesn’t work:
- Vague health scores (“they seem happy!”)
- Random dates (“every 6 months, just ask everyone”)
- The CEO’s hunch
Write down your triggers. Keep it to 2-3 to start. If you need 10, you’re overcomplicating it.
Step 3: Map Out the Actual Playbook Flow
This is where most teams get lost in “what ifs.” Don’t try to solve every scenario right away.
Start with a basic structure: 1. Trigger: What starts the playbook? (e.g., usage > 90%) 2. Action: What should happen first? (e.g., notify CSM, send templated email) 3. Follow-up: If no response, what’s next? (e.g., reminder, escalate) 4. Outcome: How do you know it’s done? (deal created, customer declined, etc.)
Example:
- Trigger: Customer hits 95% of allotted seats.
- Action: CSM gets a task to review the account and reach out with a relevant upsell offer.
- Follow-up: If no customer reply in 7 days, CSM gets a reminder.
- Outcome: CSM logs outcome (upsell, no interest, not now).
Pro tip:
Keep your first playbook as manual as possible. Let it notify humans, not “auto-email” everyone. You can add automation later once you know it works.
Step 4: Build the Playbook in Planhat
Now you’re ready to open up Planhat and actually create the playbook. Here’s what to do:
4.1. Go to Playbooks
- In Planhat, navigate to the Playbooks module.
- Click “Create Playbook.” Name it something clear (e.g., “Seat Cap Upsell”).
4.2. Set the Trigger
- Choose the trigger type (usage, renewal date, support request, etc.).
- Use filters to target only the right customers (e.g., “seat usage > 90%” AND “not already on top plan”).
Honest tip:
If you’re not sure your data is accurate, double-check before turning anything live. You want to avoid embarrassing misfires.
4.3. Add Tasks and Actions
- Assign a task to the CSM or account owner: “Review account for upsell opportunity.”
- Add a templated email (optional): Make it editable so reps can personalize, but don’t force a script.
- Set a due date for follow-up—don’t let things sit forever.
4.4. Automate Reminders and Escalations
- If the task isn’t completed in X days, trigger a reminder.
- If still ignored, escalate to a manager or flag in a report.
4.5. Track Outcomes
- Add a field or dropdown for the CSM to log the outcome: “Upsell Closed,” “No Interest,” “Follow-up Later,” etc.
- This gives you data to improve your playbooks over time (and to show what’s actually working).
Step 5: Pilot with a Small Group First
Don’t roll out to everyone. Pick a few CSMs or a small segment of customers. See what breaks, where the playbook annoys people, and what steps get skipped.
- Ask for honest feedback (“Which steps felt pointless?”)
- Watch for “automation fatigue”—too many tasks and reminders.
- Adjust before scaling up.
Step 6: Measure What Matters—Not Just Activity
It’s easy to pat yourself on the back for “20 upsell tasks created.” But if nobody’s closing, it’s noise.
Track: - Conversion rates: How many playbook-triggered actions led to actual upsells or cross-sells? - Time to follow-up: Are reps acting quickly, or sitting on tasks? - Customer feedback: Are people annoyed by the outreach, or is it relevant and helpful?
Ignore: - Vanity metrics (“We sent 1,000 emails!”) - Overcomplicated dashboards
Pro tip:
A simple spreadsheet tracking “playbook trigger → action → outcome” is often more insightful than any fancy dashboard.
Step 7: Keep It Simple, Tweak, and Repeat
The best teams treat playbooks as living documents. What worked last quarter might flop if your product or customer base shifts. Don’t be afraid to scrap what’s not working.
- Regularly review outcomes: What triggers actually lead to more revenue?
- Prune steps that get ignored or skipped.
- Add new playbooks only when the old ones are running smoothly.
What to avoid:
- Overengineering (“If customer does X between 2-4 pm, but only on Tuesdays…”)
- Letting playbooks get stale. If nobody uses them, kill them.
Example: A Simple Upsell Playbook
Here’s what a straightforward seat expansion playbook might look like in Planhat:
- Trigger: Customer uses 95% of licensed seats for 3 consecutive days.
- Action: CSM gets a task: “Customer nearing seat limit—review for expansion opportunity.”
- Optional: Templated email to customer: “Looks like you’re growing! Want to chat about adding more seats?”
- Follow-up: If no response in 5 business days, CSM gets a reminder.
- Outcome: CSM logs result (“Upsell created,” “No interest,” “Will revisit”).
That’s it. No branching logic, no 10-step sequences. Just a nudge at the right time.
Wrapping Up: Keep It Real, Keep It Useful
Automated playbooks in Planhat can help you scale upselling and cross-selling—if you keep things simple and focused. Resist the urge to automate every edge case or flood your team with notifications. Start small, measure honestly, and iterate based on real results, not wishful thinking.
The key: Don’t let automation become another thing to manage. Use it to free up time for real conversations and smarter growth.