Recurring Revenue in ConnectWise: How to Set Up Agreements That Don’t Break Later

Recurring revenue is one of the most reliable ways to grow your Managed Service Provider (MSP) business. It provides a clearer forecast, stronger customer relationships, and healthier cash flow. But if your agreements in ConnectWise PSA are poorly set up, they can fall apart over time, taking your profit and trust along with them.

In this article, we’ll walk you through how to build dependable ConnectWise PSA agreements that truly support your recurring revenue goals.

You’ll learn how to avoid billing issues, align your service delivery with what’s promised, and make your Service Level Agreement (SLA) workflows smooth and automated.

Why Recurring Revenue Matters for MSPs

When your business is built on a recurring revenue model, you’re creating a foundation that supports long-term stability. Here’s why that matters:

• Predictable cash flow each month
• Easier long-term planning
• More accurate company valuations
• Higher client lifetime value

Managed services typically account for 60% to 80% of an MSP’s overall revenue. That kind of recurring income is what allows your business to grow consistently, even when project work fluctuates.

The key to getting there is setting up the right processes in your ConnectWise PSA system and building strong MSP partnerships. That starts with your agreements.

What ConnectWise PSA Agreements Actually Do

Think of ConnectWise PSA agreements as contracts that drive every part of your MSP’s service delivery and billing. They define:

• Which services are covered
• How frequently you invoice
• How SLAs are monitored and enforced
• What counts as billable versus included support

The way your services fit into the MSP landscape plays a big role in how you structure your agreements. When that’s clear, it’s much easier to outline what you’re offering and make sure your contracts reflect that.

In ConnectWise, that starts with choosing the agreement type that fits your model best:

• Fixed monthly fee
• Time and materials
• Block time
• Per-user or per-device

Most folks don’t think twice about how an agreement is set up until it backfires. Maybe billing doesn’t match what’s been delivered, or SLAs get missed because the fine print didn’t cover real scenarios. Either way, it adds up to lost trust and lost money.

Why Agreements Break

Here are the most common issues we see when agreements aren’t properly managed:

• Billing cycles don’t reflect actual service usage
• SLAs aren’t tied to tickets or boards correctly
• Additions aren’t automated, so billing stays static
• Time entries aren’t mapped to agreements

If you’re seeing gaps in billing or client disputes over coverage, chances are one of these breakdowns is the reason. It’s rarely one big mistake. Most often, it’s small setup oversights that pile up.

How to Create Agreements That Work Long Term

Here’s a simple checklist to follow when setting up your ConnectWise PSA agreements:

Match agreement type to service

Don’t try to force all clients into a single agreement model. Instead, align based on the type of service you provide.

If your services are tied to endpoints or user counts, using auto-additions ensures billing keeps up with growth.

Get billing cycles right

Instead of just monthly invoices, think through:

• Should this be billed annually but paid monthly?
• Are new additions prorated mid-cycle?
• Do you need to schedule usage reviews every quarter?

Make sure your agreement reflects how the client consumes the service.

Connect SLAs to each agreement

Every MSP SLA needs to be enforced, not just promised. You can do this inside ConnectWise by:

• Attaching SLA templates to the right service boards
• Making sure ticket statuses trigger SLA timers
• Pausing timers for client-dependent statuses like “Waiting on Customer”

If your SLAs are just written in a PDF but not wired into your ticketing process, you’re setting yourself up to fail.

Automate agreement maintenance

One of the best features in ConnectWise PSA is the ability to automate agreement additions. That includes:

• Auto-adding users and devices based on integrations
• Adjusting quantities without manual tracking
• Triggering alerts when usage exceeds limits

When combined with billing automation, this creates a tight loop that ensures you're always charging accurately.

Link agreements to service boards

Your support tickets should always be mapped to the correct agreement. If they aren’t, you risk losing billable time. To stay on track:

• Set defaults at the board level
• Assign the right agreement per ticket
• Validate that time entries are flagged correctly

This helps avoid revenue leakage and makes your billing cycle easier to audit.

Monitor agreements after setup

Building the agreement is just step one. Monitoring is what ensures long-term success. You’ll want to:

• Run profitability reports per agreement
• Check SLA performance weekly
• Validate additions against service logs

Using built-in reporting tools, you can view margins, service usage, and potential gaps in real time.

Manage mid-cycle changes

Clients evolve. They hire more people, switch services, or add locations. Instead of ripping and replacing agreements, you can:

• Use the Additions tab to reflect new users or devices
• Modify billing rules mid-cycle without disrupting the rest
• Track changes for audit and renewal purposes

This way, you stay in sync with the client’s growth while keeping the revenue cycle intact.

Use SLAs to drive your service quality

An MSP SLA is a promise you make with real-time impact. When combined with ConnectWise SLA workflows, you can:

• Create escalations before a breach happens
• Stop the clock when you’re waiting on the client
• Highlight recurring delays in your reporting

Your service desk team benefits from clarity, and clients know what to expect. It builds accountability on both sides.

Strong recurring revenue depends on well-structured, actively managed ConnectWise PSA agreements. When your agreements are properly aligned with services, billing, and SLAs, they create a dependable revenue stream that reflects the value you deliver.

Avoiding breakdowns starts with getting the setup right, from choosing the right agreement type to automating additions and linking SLAs. But the real impact comes from consistently reviewing, refining, and adapting your agreements as clients grow and needs change.

With the right framework in place, your agreements will support your business instead of slowing it down. At Bering McKinley, we help MSPs build agreement frameworks that hold up under pressure and scale with confidence.

Schedule a meeting today to make your recurring revenue truly reliable.

Key Takeaways

• Recurring revenue gives MSPs room to plan and grow
• Agreements define what’s included, what gets billed, and when
• Missing a few settings can throw off billing or SLA tracking
• Choose agreement types based on how you actually deliver services
• Automating additions helps billing stay current as clients change
• If time entries don’t link to an agreement, money can fall through the cracks
• SLAs need to follow how your team handles tickets, not just sit in a doc
• It helps to review agreements regularly

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