Most sales leaders at $10M–$50M companies think enterprise lessons don't apply to them yet.
Wrong.
I scaled business units at Vocus from $10M to $400M. The problems that broke teams at $100M were the same problems we ignored at $30M. We just had more people and more revenue when they finally forced us to fix them.
Here are six lessons that worked at scale. You need them now.
1. Make Your Product Easy to Sell
If your product is hard to sell, people stop selling it.
Not because they're lazy. Because they have 50 other things to do and bureaucracy saps their will to live.
Here's what happens: One deal goes sideways. Legal freaks out. CFO wants new approval processes. Technical team adds three new sign-off steps. Suddenly a deal that took two weeks now takes six.
Your reps don't complain. They just quietly start selling the easier product. Or they leave.
The fix: Get ruthless about quantifying risk.
When someone wants a new approval layer, make them explain the actual cost of the problem versus the cost of slowing down every deal. One bad contract isn't worth killing velocity on 100 good ones.
Your job is to keep the bureaucrats from turning a one-off issue into permanent friction. Explain it's manageable. Promise you'll watch for patterns. Then move on.
Speed matters more than perfect process.
2. Understand Profitability
This sounds obvious. Most companies still get it wrong.
They understate the profitability of their best product and overstate the profitability of their worst. Then they wonder why revenue grows but profit doesn't.
I get it, exact profitability is hard. Multiple product lines, shared costs, allocation assumptions. But hard doesn't mean impossible.
Here's the test: Can you get finance and technical teams to agree on a profitability model?
If yes, you're probably close enough. If no, you're guessing.
And if you're guessing at profitability, everything breaks:
- Your incentive plan rewards the wrong behaviour
- Your discounting guidelines aren't anchored in reality
- You scale revenue that doesn't make money
Fix this before you hit $20M. After that, the wrong incentives are embedded in 30 people's comp plans and you're stuck.
3. Business Rules Are Your Special Sauce
Business rules are how your company actually operates:
- What reps can discount
- How products get configured
- What terms you'll sign
- How deals get approved
Most companies keep this stuff in people's heads. Terrible idea.
Business rules only work if they're:
- Written down
- Findable
- Used
- Enforced
If they're not documented, you can't complain when people don't follow them. If they're documented but not enforced, they're not real.
I've seen companies lose millions because the discount policy lived in one person's email and nobody else knew it existed. I've seen reps sign terms that gutted profitability because "that's how we've always done it" and nobody wrote down why we stopped.
Your business rules are as real as you make them. Make them real.
4. Align Incentives to What the Business Wants
I see this constantly: Product A has 80% margin. Product B has 30% margin. Sales team earns the same commission on both.
Insane.
Your reps will sell what's easiest or what pays the most. If you pay them the same for low-margin products, they'll sell low-margin products. Then you'll wonder why revenue is up but profit isn't.
The fix is simple: Pay more commission on what you want them to sell.
Higher margin? Higher commission. Strategic product? Higher commission. Longer contract? Higher commission.
Your incentive plan is a signal. It tells your team what actually matters. If the signal doesn't match your strategy, the strategy loses.
This isn't complicated. But you'd be shocked how many companies get it wrong.
5. Avoid Clawbacks
Clawbacks poison culture.
Yes, you need the ability to claw back commission if a deal falls apart. But if you're clawing back regularly, you've built the wrong process.
Better approach: Document commission rules that minimise clawbacks before they happen.
Work out every scenario where finance might ask for a clawback. Then write down what happens.
Example: Sales rep sells a 24-month deal. Customer uses it for 7 months, then goes out of business. What happens to the commission?
My rule: If the rep operated in good faith and followed all the business rules, they keep the commission. It's a business problem, not a sales problem.
Your rule might be different. Fine. Just write it down and get finance to agree before anyone sells anything.
Make commission eligibility clear:
- CRM filled in correctly
- Deal qualified properly
- Contract signed
- Business rules followed
No eligibility until those boxes are ticked. No surprises later.
Clawbacks create paranoia. Reps start gaming the system, hiding information, closing deals that barely qualify just to hit a number before you change the rules.
Build commission rules everyone understands. No surprises. And if you really do need to claw back a payment, take it out of the next commission check, not six months later.
6. Goals and Values Drive Alignment
Fast-growing companies either align around clear goals and values, or they turn into chaos.
At Vocus, I spent huge amounts of time making sure every person on my team understood:
- Where the company was going
- How their role helped us get there
- What behaviours we valued along the way
This wasn't motivational poster stuff. It was operational.
When everyone knows the goals and values:
- They make better decisions without asking you
- They row in the same direction
- You don't have to micromanage
When they don't:
- Every decision comes back to you
- People pull in different directions
- You spend all day firefighting
The difference between a $10M company and a $100M company isn't complexity. It's alignment.
You can't scale by making every decision yourself. You scale by making sure your team makes the same decisions you would.
That only works if they know what you're trying to build and how you want to build it.
The Point
These aren't enterprise problems. They're revenue problems.
Ignore them at $10M and you'll be fixing them at $50M with 10x the people and 10x the pain.
Fix them now. You'll thank yourself later.