Why Your New Sales Hire Isn't Closing (And It's Not Their Fault)

Introduction

You finally hired a salesperson. Maybe your first VP of Sales. Everyone's excited. Pipeline is about to flow. Revenue is coming.

Three months later: Minimal deals closed. The rep is frustrated. You're frustrated. Leadership is asking questions.

What happened?

Here's the truth: Your sales hire isn't the problem. Your company wasn't ready for them to close deals.

This guide explains why this happens at almost every company hiring their first sales leader, what infrastructure you're missing, and how to set realistic expectations so both you and your sales hire succeed.

---

The Pattern: Two Real Stories

Story 1: When Your #1 Seller Can't Close

A company hired their absolute best seller—the #1 rep in the entire organization—to launch a new vertical. Everyone was pumped. This rep had a proven track record. Big deals. Consistent quota attainment. A killer.

The rep brought deals to the table... and hit a wall.

What broke:

Paper wasn't right: The company's existing MSA was designed for order forms. The new customer segment wanted SOWs (Statements of Work) and purchase agreements. Legal didn't know how to adapt.

Operations pushed back: "We can't fulfill that size deal. You can only close smaller deals." But who was operations to tell sales what they could close? Tension and finger-pointing followed.

Deal desk confused: They'd never papered this type of deal before. Everything took weeks to figure out.

Legal blocked: "What are SLAs? We've never done these. How are we supposed to draft language for this?"

Comp got tangled: Who approves what? How does this affect the rep's compensation? Nobody knew.

The reality:

The person who hired the rep ended up spending their time building infrastructure across operations, finance, legal, engineering, and HR—basically every function—just so the company could close business.

Eventually, they closed $10M. But only after months of building the internal machinery that should have existed before the sales hire started.

Story 2: The Systematic Bottleneck

A deep tech company generated tons of demand. Strong market tailwinds. Product-market fit was clear. They hired an awesome VP of Sales to capitalize on it.

The VP couldn't close anything.

Why:

• No clear pricing structure
• No discount approval process
• Couldn't quote without engineering sign-off (which took 1.5 weeks minimum)
• Everything required cross-functional alignment that didn't exist

The frustration loop:

Sales hire: "I'm here to close business. I'm compensated to close business."

Company: "We're not actually ready for you to close business."

Result: Friction. Frustration. Missed deals.

None of the infrastructure was built. The org hadn't done the work to iron out pricing, legal, operations, or approval workflows. They were relying on new customers to provide the requirements—and the sales hire to somehow figure it all out.

---

Recognizing the Symptoms: Your Sales Hire Is Stuck

If you're hearing these questions or complaints repeatedly, you have infrastructure gaps.

Pricing & Approvals

• "What should I quote for this?"
• "Who approves discounts over X%?"
• "Can I bundle these products, and if so, at what price?"
• "Engineering won't give me a quote without 10 days of meetings"

Legal & Contracts

• "The customer wants an SOW but we only have order forms"
• "They're asking for SLAs—do we have standard language?"
• "Legal says they need to review this type of deal, but they're backed up 3 weeks"
• "Our MSA doesn't cover this use case"

Operations & Fulfillment

• "Can we actually deliver what I'm selling?"
• "Operations says we can't fulfill deals this size"
• "Who owns post-sale handoff?"
• "What's our onboarding process?"

Process & Systems

• "Where do I enter this in the CRM?"
• "Who needs to approve this before I can send a contract?"
• "How do I generate a quote?"
• "What's the approval workflow for custom deals?"

If your sales hire is asking these questions repeatedly, they're not the problem. Your infrastructure is.

---

Why This Happens: The Infrastructure Gap

Companies Think

"We just need a salesperson to close deals."

Reality

Sales can't close until organizational infrastructure exists.

What's Actually Missing

• Clear pricing and packaging
• Discount approval workflows
• Standard legal paper (MSAs, order forms, SOWs)
• Operations readiness to fulfill what's being sold
• Product catalog and quoting process
• Deal desk function (or at least clarity on who does what)
• Cross-functional alignment on what you can and can't sell

The Painful Truth

New customers reveal the edges of what you haven't built.

Your first sales hire isn't just closing deals. They're teaching the organization how to fulfill customer demand. They're surfacing all the gaps in your infrastructure.

This takes time. Often 6-12 months to build out properly.

---

The Infrastructure Checklist: What to Build

Before or alongside your first sales hire, you need the following. Prioritize based on your existing infrastructure and capabilities. The parts of your org that are already strong? Great—check those boxes. The parts that are weak? Focus there first.

Also: Start thinking about what's essential vs. nice to have. Your first set of customers will tell you exactly how to prioritize this. They'll show you what's blocking deals and what you can defer.

Pricing & Packaging

• Clear pricing for each product/service
• Defined discount approval levels (who can approve what %)
• Pricing for common bundles or configurations
• Process for custom pricing requests

Legal & Contracts

• Standard MSA (Master Services Agreement)
• Order form or SOW template
• SLA language (if applicable)
• Redline approval process
• Terms that match your new customer segment

Operations & Fulfillment

• Documented fulfillment process
• Capacity planning (can you actually deliver?)
• Post-sale handoff workflow
• Onboarding process for new customers

Sales Process & Tools

• CRM setup and process
• Quote generation process
• Approval workflows (discount, custom deals, etc.)
• Sales collateral (decks, one-pagers, case studies)

Cross-Functional Alignment

• Engineering involvement in quotes (when/how)
• Finance approval requirements
• Product roadmap visibility (what can you sell vs. what's coming)
• Deal desk or point person for complex deals

Compensation Structure

• Clear comp plan
• What counts as "closed" for commission
• How custom/strategic deals affect comp

(For detailed guidance on structuring comp for your first sales hire, see our companion guide: "How to Structure Comp for Your First Sales Hire")

---

What to Do Differently: Set Realistic Expectations

Structure Your First Sales Hire for Learning, Not Just Closing

Compensation approach for Year 1:

• Strong base salary, minimal variable
• OR no variable component at all for first year
• Revisit after infrastructure is built

Why this works:

• You want a seller who will hunt deals AND help you learn
• Their job isn't just closing—it's teaching the org what infrastructure you need
• Removes frustration of "I can't earn because the company isn't ready"
• Aligns incentives: build the machine together

Set the expectation:

• "First 6-12 months, we're building the infrastructure together"
• "You'll bring deals, we'll figure out how to close them"
• "Your value is teaching us what customers need, not just quota attainment"

How to Explain This During the Interview Process

Be honest and transparent. People need to know what they're getting into. If they know, they can decide if they're comfortable with it. If they're not, they shouldn't take the role—and you should be able to filter them out.

What to say:

"Here's the reality: We're building the sales infrastructure as we go. You'll be bringing deals, but you'll also be teaching us what we need to close them. That means working cross-functionally with legal, ops, finance, and product to build pricing, contracts, processes—all of it.

Your first 6-12 months won't be pure quota attainment. It'll be a mix of hunting deals and building the machine. If you're someone who thrives in that environment, this is a great opportunity. If you want a fully-built sales org where you just carry a bag, this isn't the right fit."

Screen for the Right Skills

You're not looking for someone who's just hit President's Club. You're looking for someone who's created change across multiple departments.

What to screen for:

• Cross-functional collaboration: Have they influenced product decisions? Driven change across ops, legal, or finance?
• Customer discovery: Can they gather requirements from customers and translate them into internal action?
• Building, not just executing: Have they built processes, comp plans, or sales infrastructure before?

Green flags:

• "I worked with product to refine our pricing based on customer feedback"
• "I built the first sales comp plan at my last company"
• "I partnered with legal to create our first enterprise MSA"

Red flags:

• "I hit President's Club three years running" (Great! But can you do more than carry a bag?)
• "I'm very uncomfortable with moving goalposts" (This role IS moving goalposts)
• "I just want to sell" (You need someone who can sell AND build)

How to Measure Success in Year 1

Traditional quota attainment isn't the right metric. Here's what to measure instead:

1. Booked revenue / contracted deals

• How much revenue have you contracted for?
• Recognize the goalposts will move throughout the year—be flexible

2. Infrastructure built

• Did we create pricing? Legal templates? Fulfillment processes?
• What can we now do that we couldn't before?

3. Customer learnings

• What did we learn about our ICP?
• What requirements surfaced that we didn't anticipate?
• How did this shape our product or GTM strategy?

4. Cross-functional impact

• Did the sales hire successfully collaborate across teams?
• Are other departments better equipped to support sales now?

Bonus points: Sales hires who've built comp plans in the past. They'll empathize with this environment. They'll understand the challenge. They can even help structure comp for the org based on where it is and where it's going.

---

The Result: A Sales Hire Who Succeeds

What You've Built

• Infrastructure that allows sales to actually close
• A sales hire who understands the business, not just their territory
• Processes that scale as you add more sellers
• Realistic timeline for ramping revenue
• Cross-functional collaboration that didn't exist before

What You've Avoided

• Frustrated sales hire who quits after 6 months
• Finger-pointing between sales and other functions ("Sales won't close" vs. "The company won't let us close")
• Missed deals because "we couldn't paper it"
• Building infrastructure reactively instead of proactively

The Uncomfortable Truth

Your first sales hire will close less than you hope in Year 1.

That's okay. Their job is to build the machine WITH you. Once it's built, scaling becomes much easier.

The worst thing you can do is pretend the infrastructure already exists. Be honest. Hire for the reality. Build together.

That's how you turn your first sales hire into a long-term asset instead of a short-term disappointment.