Client on $150 monthly maintenance. One conversation. Now paying $550 monthly.
Here is how to upgrade existing clients without being pushy.
THE SETUP:
6 months into maintenance contract. Invoice processing running smoothly. Monthly check-in call scheduled.
THE CONVERSATION:
Me: "How is everything running?"
Her: "Great. Invoices are handled. Life saver."
Me: "Glad to hear it. What is taking up most of your time now?"
Her: (pause) "Honestly? Expense reports. My team submits receipts and I spend hours organizing them."
Me: "How many expense reports monthly?"
Her: "About 60 across 8 employees"
Me: "How long does processing take?"
Her: "Maybe 12 hours total"
Me: "Want me to automate that too?"
THE EXPANSION PROPOSAL:
Added expense report automation to existing system
Same tech stack (Make.com plus PDF Vector)
Builds on infrastructure already in place
Setup: $800 (discounted from $1,200 for existing client)
Monthly increase: $400 (from $150 to $550)
Annual revenue increase: $4,800 plus $800 setup
THE PSYCHOLOGY OF EXPANSION:
They already trust you
They see results from first project
Adding more is low risk for them
You understand their business
Implementation is faster (systems already connected)
THE MONTHLY CHECK-IN FRAMEWORK:
Every maintenance call, ask these 3 questions:
1. "How is the current automation performing?"
(Opens conversation, shows you care)
2. "What is taking up most of your time now?"
(Identifies new pain points)
3. "Anything else you wish happened automatically?"
(Plants automation seeds)
THE EXPANSION OPPORTUNITIES:
Invoice processing clients often need:
- Expense report automation
- Purchase order matching
- Vendor onboarding
- Contract tracking
Form processing clients often need:
- Follow-up automation
- Data validation
- Reporting dashboards
- Multi-location rollout
THE PRICING FOR EXPANSIONS:
Existing clients get 20-30% discount on setup
Monthly increase matches scope
Package deals for multiple expansions
This keeps them loyal and increases lifetime value.
MY EXPANSION STATS:
Maintenance clients: 12
Expansion conversations: 12
Expansions sold: 7
Average monthly increase: $280
Total monthly revenue added: $1,960
THE EXPANSION SEQUENCE:
Month 1-3: Deliver excellent service on original project
Month 4: First expansion question in check-in
Month 5-6: Proposal if pain point identified
Month 6+: Ongoing monthly expansion conversations
THE CLIENT LIFETIME VALUE MATH:
Without expansion:
$1,800 setup plus $150 monthly times 12 months = $3,600 year 1
With expansion:
$1,800 plus $800 setup plus $550 monthly times 12 months = $9,200 year 1
Same client. 2.5x revenue.
YOUR HOMEWORK:
List all current maintenance clients
Schedule monthly check-in with each
Ask the 3 questions above
Identify one expansion opportunity
Send proposal within 48 hours
Your next $400 monthly is probably in your existing client base.
What current client has another pain point you could solve?