
You closed the first 20 customers yourself. You know the pitch cold. You know which objections to expect, which prospects are serious, and how to handle pricing conversations without flinching.
The problem? Your team doesn't. And instead of fixing that, you've quietly become the person every deal runs through.
A rep needs to offer a discount: they Slack you. A prospect asks a technical question on a demo: they add you to the call. A new lead comes in from an enterprise company: they wait for you to decide if it's worth pursuing.
This isn't a team problem. It's an architecture problem. And it's costing you growth you can't see on any dashboard.
At this stage, you're big enough to have a sales function, but small enough that most of the institutional knowledge still lives in your head. That's the trap.
When you were selling alone, your judgment was the process. It worked because you were fast, context-aware, and accountable. But when you hired your first two or three reps, you never fully transferred that judgment. You transferred tasks — go prospect into this segment, book demos — but not decision-making frameworks: here's how to qualify a lead, here's when to offer a discount, here's when to walk away.
So your team executes the easy, visible parts of the job. And escalates everything that requires judgment — which is most of what actually moves a deal forward.
The result: your calendar fills up with deal reviews, quick questions, and approval requests. Your reps feel stuck waiting. Deals slow down. And you, running between strategic planning and a call with a prospect at 5pm, wonder why growth feels so hard with a team this size.
Check how many of these apply to your current week:
If 3 or more of these are true, you are the bottleneck. Not your team, not your market, not your product.
For one week, keep a simple log. Every time a rep comes to you with a question or approval request, write it down: what was the question, what was your answer, and why.
At the end of the week, you'll have a list of 15–30 recurring decisions. Most of them follow a pattern. Those patterns are your starting point for documentation.
Example: If you keep getting asked whether to give a prospect a 15% discount, your answer probably depends on company size, deal size, and whether they're in your core ICP. Document that logic. Turn it into a one-page pricing authority matrix: who can offer what discount, under what conditions, without needing your approval.
Most B2B teams have an ICP that reads like a LinkedIn filter: SaaS companies, 50–500 employees, using Salesforce. That's a target segment, not an ICP.
A real ICP gives your team enough signal to make a call. It includes firmographics (size, industry, tech stack, geography), situation signals (what's happening at the company right now that makes them a good fit), disqualifiers (what makes someone a bad fit even if they look right on paper), and 3–5 qualification questions your rep must get answers to before a deal moves forward.
Put this in a one-page document. Train your team on it. Make it a required field in HubSpot before a deal can move to Demo Scheduled.
You don't need to write a 40-page sales playbook. You need to capture what works and make it accessible. Start by recording your next 5 discovery calls (with permission). Pick the 2 that went best. Identify the 3–5 questions you asked that opened up the real conversation. Write those questions down in a one-page discovery call guide.
That's your first asset. It's not a script. It's a framework your reps can use to run calls with the same depth you bring — without being you. Add to it over time: your best objection responses, your go-to framing for pricing conversations, your close sequence.
Right now, HubSpot is probably a graveyard of deals that haven't moved in 60 days and contacts that were never properly qualified. That's not a HubSpot problem — it's a process problem. But HubSpot can help you fix it.
Required fields per pipeline stage: Before a deal moves from Lead to Demo Scheduled, require ICP tier (A/B/C), budget confirmed (yes/no), and decision-maker identified (yes/no). This forces your team to qualify before they advance, not after.
A Zombie Deal view: Create a saved filter showing deals in stage 2 or higher with no activity in the last 21 days. Review every Monday. If a deal can't be revived in one touch, close it as lost. A clean pipeline is a trustworthy pipeline.
A qualification score property: Create a custom property called ICP Score (A/B/C/D), required before a deal moves past qualification. This lets you report on deal quality over time, not just deal volume.
Right now, the default is: when in doubt, ask the founder. That needs to flip: handle it, document it, then tell me.
Write a one-page escalation guide covering what decisions a rep can make unilaterally (small discounts, demo scheduling, proposal wording), what needs team lead approval (larger discounts, non-standard terms), and what needs founder approval (strategic partnerships, deals that change your positioning, large contracts). Put it in Notion. Reference it in your next team meeting. Then enforce it.
There's a version of this story that ends well: the founder extracts their knowledge into systems, the team executes with real autonomy, and the founder finally works on the business instead of in every deal.
There's another version where the founder stays the bottleneck until they burn out or hire an expensive VP of Sales who also can't fix the problem — because the problem was never headcount.
The difference between those two versions isn't talent or market. It's whether you treat how you sell as something that lives in your head, or as something you've actually designed.
Where are you right now — is your sales process something your team runs, or something they ask you to run for them?