90-Day Sales Scorecard: Is Your Head of Sales Fit for Purpose?
You hired a head of sales but you're still missing targets. Five measurable metrics to evaluate whether the problem is your sales leader, your product-market fit, or both — before you make an expensive mistake.
You hired a head of sales, but you’re still missing sales targets and wondering: “Is it the head of sales or our product-market fit?”
If you’re asking this, the answer is probably both.
I assess five measurable metrics in any B2B sales process to clarify whether your head of sales is fit for purpose — and what to do about it.
The Five Metrics
1. Quality of Meetings
Are you getting meetings with decision-makers at companies that match your ideal customer profile? A red flag: meetings with companies outside your target, or with people who don’t have the problem you’re addressing. (This is why narrowing your ICP accelerates results.)
Volume of meetings is easy to fake. Quality is harder. One well-qualified meeting with a genuine economic buyer is worth more than ten with enthusiastic middle managers who can’t sign a contract.
2. Progression of Leads
Are leads moving through the funnel — from initial discussions to product demos or POCs — or stagnating at early stages? When there’s a real problem and you’re talking to the right people, even large enterprise companies move quickly. Stagnation is a signal, not a patience test.
3. Depth of Discovery Calls
Is your head of sales asking questions that uncover meaningful pain points, or waiting for you to do all the talking? Our MEDDIC framework provides a structured approach to evaluating discovery quality.
The best salespeople identify specific challenges instead of staying at a surface level. If you’re not impressed with the questions they ask when you’re in the room, they’ll do an even worse job when you’re not.
4. Building Relationships
Are they fostering trust and rapport with potential clients? Consistent follow-ups and strong connections result in engaged prospects. Weak follow-ups leave clients disengaged — and create the impression your company isn’t serious.
5. Proactive Feedback Loop
Do they actively seek feedback from clients and your team to refine their approach? A strong performer constantly adapts. A lack of feedback-seeking often indicates rigid or ineffective methods — and someone who’s managing their own narrative rather than improving.
The Most Important Two
As you scale, meeting quality and lead progression matter most. You can coach discovery technique. You can improve relationship-building with training. But if someone is consistently booking the wrong meetings with the wrong people, and those meetings aren’t progressing — that’s a hiring problem, not a coaching problem.
How to Use This Scorecard
Step 1: Agree clear metrics with your head of sales in advance. Track them weekly — yes, weekly, even in enterprise sales. Weekly tracking doesn’t mean micromanagement; it means you catch problems before they become expensive.
Step 2: Agree on shared definitions. What does “decision-maker” mean — verbal confirmation they can sign off on the required budget? What does your ICP look like in terms of company size, industry, and buying process? What does “good progression” mean — expected weeks from first meeting to demo, demo to follow-up?
Step 3: Ask your head of sales to self-assess against these metrics. Push for specifics. Don’t settle for fluff. How a salesperson talks about their own performance tells you as much as the performance itself.
Step 4: Focus on Meeting Quality and Lead Progression as your leading indicators. Everything else follows from these two.
The Hardest Part
Most founders wait too long before having this conversation. They give benefit of the doubt for 6–9 months because firing a senior hire is uncomfortable and expensive. But the longer you wait, the more runway burns, and the more you confuse “head of sales underperformance” with “product isn’t ready.”
Set expectations at 30 days. Assess at 60. Decide at 90.
Unsure if your sales challenges are a leadership problem, a PMF problem, or both? This is one of the most common diagnostics we run at VECTOR. Apply to work with us — or read The Founder’s Guide to Senior Hires before making your next hire.