The Salesforce instance that got you to $5M in revenue is probably not the one that will get you to $20M.
That’s not a criticism—it’s just how startups work. In the early days, you needed something that was “good enough.” You configured it yourself, or had someone set it up quickly, or inherited it from a founder who watched a few Trailhead videos. And it worked! You closed deals, tracked customers, ran some reports.
But growth has a way of exposing every shortcut, every workaround, and every “we’ll fix that later” decision. Here are the signs that your Salesforce has hit its limits—and that “later” has arrived.
1. Quarter-End Is a Fire Drill
If your team spends the last week of every quarter “cleaning up Salesforce” just to produce accurate numbers, your system isn’t serving you—you’re serving it.
What this looks like:
- Sales Ops manually updating Opportunity stages and amounts
- Frantic Slack messages asking “is this deal going to close?”
- Reports that require exports to Excel for “adjustments”
- Numbers that don’t match between Salesforce and finance
What it means: Your data model doesn’t reflect how your business actually works. Opportunities aren’t structured to capture the information you need for forecasting.
2. Nobody Trusts the Dashboards
When executives stop looking at Salesforce dashboards and start asking for manual reports, you have a credibility problem.
What this looks like:
- “Can you pull the real numbers?” requests
- Dashboards that everyone knows are “directionally correct” at best
- Multiple versions of the same report with different answers
- Key metrics tracked in spreadsheets “because Salesforce can’t do it”
What it means: Either the data going in is bad, the reports are built wrong, or both. Usually both.
3. Your Team Has Workarounds for the Workarounds
Every system has workarounds. But when those workarounds have their own workarounds, you’ve built a house of cards.
What this looks like:
- “Oh, don’t use that field—use this one instead”
- Tribal knowledge about which picklist values actually mean what
- Processes that require checking multiple places for the same information
- New hires who take months to understand how things “really” work
What it means: The system has drifted so far from its intended design that it’s now actively working against you.
4. You Can’t Answer Basic Questions
How many customers do we have? What’s our churn rate? Which product is growing fastest? If answering these questions requires a research project, your CRM isn’t doing its job.
What this looks like:
- “Let me get back to you on that” for straightforward questions
- Conflicting answers depending on who you ask
- Analysis paralysis because no one trusts the data
- Decisions made on gut feel because the data is too hard to extract
What it means: Your data model wasn’t designed for the questions you’re now asking. This is common when businesses evolve—the questions at $2M aren’t the questions at $10M.
5. Integrations Are Duct-Taped Together
You added marketing automation. Then a support tool. Then a billing system. Then a data enrichment service. Now nothing quite talks to each other, and you have five different “sources of truth.”
What this looks like:
- Manual data entry between systems
- ”Which system has the right information?” debates
- Sync errors that require regular cleanup
- Processes that break when someone changes something in one system
What it means: Integrations were added tactically without an overall architecture. Each one solved an immediate problem but created long-term complexity.
6. You’re Paying for Features You’re Not Using
Salesforce licensing isn’t cheap. If you’re paying for Sales Cloud, Service Cloud, and a handful of add-ons but only using basic CRM functionality, you’re leaving money on the table—or spending money you don’t need to spend.
What this looks like:
- Features that were “on the roadmap” for two years
- Licenses for tools nobody has logged into in months
- Workarounds that replicate functionality you’re already paying for
- ”We should really use that” conversations that never go anywhere
What it means: Either you’re over-licensed for your needs, or you’re under-utilizing what you have. Both are fixable.
7. The Person Who Set It Up Is Long Gone
And they didn’t leave documentation.
What this looks like:
- Flows and automations that nobody understands
- ”Don’t touch that—it might break something”
- Fear of making changes because of unknown dependencies
- Orphaned fields and objects that may or may not be doing something important
What it means: You have technical debt, and it’s compounding. The longer you wait to address it, the harder (and more expensive) it becomes.
What To Do About It
If you recognized your company in three or more of these signs, it’s time to take action. The good news: you don’t necessarily need to start over.
Step 1: Assess the damage. Before fixing anything, understand what you’re working with. What’s the data model? What automations exist? What’s actually being used versus what’s just sitting there?
Step 2: Define what “good” looks like. What questions do you need your CRM to answer? What processes does it need to support? Work backward from business outcomes, not Salesforce features.
Step 3: Prioritize ruthlessly. You can’t fix everything at once. Identify the highest-impact, lowest-effort improvements first. Build momentum with quick wins.
Step 4: Fix the foundation before adding more. Don’t layer new tools on top of broken processes. Get the data model right, get the core workflows working, then expand.
Step 5: Get help if you need it. There’s no shame in bringing in someone who’s seen this pattern before. A few hours of expert guidance can save months of trial and error.