Breaking Into Enterprise Sales: Strategies for Targeting and Closing Big Deals

I once worked with a startup founder who landed a meeting with a Fortune 500 prospect. He was thrilled.“This is the one,” he said. “If we close them, we’re set.”

Three months later, the deal was dead.

What happened?

He had one champion, no plan for procurement, no backup contacts, and no visibility into the decision-making process.The champion left. The momentum vanished. So did the deal.

Enterprise sales is not just about getting in the door. It is about staying in the room. Across teams, timelines, and shifting priorities.

Let’s break down how to do it right.

Step 1: Target the Right Enterprise Accounts

Not all big companies are worth chasing. The best enterprise deals come from accounts that are:

• Actively investing in your category

• Aligned with your ICP and proven use cases

• Showing intent or change signals like hiring, funding, or market expansion

How to spot them:

• Use tools like 6sense, Bombora, or LinkedIn Sales Navigator

• Look for accounts similar to existing customers

• Prioritize those with urgency and budget

Step 2: Multi-Thread or Risk Losing the Deal

Enterprise sales means buying committees. One contact is not enough.

Stakeholders to expect:

• VP or C-level approver

• Hands-on champion

• Procurement and legal

• IT or security gatekeeper

What to do:

• Engage multiple stakeholders early

• Tailor messaging to each role’s priorities

• Equip your champion to sell internally

Step 3: Master the Enterprise Sales Process

Here’s how top SaaS sellers structure the journey:

Stage 1: Target and Engage

• Map the org chart

• Personalize outreach across LinkedIn, email, and intro paths

• Show up with insight, not just a pitch

Stage 2: Discovery and Qualification

• Go deep. Enterprise buyers expect you to understand their world

• Ask impact questions:

  • “What happens if this goes unsolved this quarter?”

  • “What’s the real cost of this pain?”

Stage 3: Navigate the Buying Process

• Learn their procurement workflow early

• Align with finance, legal, and security teams before they raise red flags

• Address friction before it shows up

Stage 4: Close and Expand

• Use Mutual Action Plans to formalize steps

• Offer pilot programs to ease risk

• Build post-sale relationships for upsell opportunities

Step 4: Negotiate Without Losing Margin

Enterprise buyers will push hard. You need to hold your ground.

How to win the negotiation:

• Never lead with a discount. Anchor on ROI

• Link pricing to outcomes, not features

• Be flexible on structure (multi-year, phased rollout), not just price

STRATEQS' Perspective: Big Deals Require Big Discipline

You don’t win enterprise by hoping. You win with process.

Here’s what high-performing SaaS teams do consistently:

• Focus on accounts that signal real opportunity

• Multi-thread early and often

• Match the buyer’s process instead of forcing your own

• Sell on value and navigate negotiations with intent

  
  

Let’s Build an Enterprise Sales Motion That Closes

Give me a call to learn more how we could help you win enterprise deals. On our first call, we’ll:

• Pinpoint where your deals are stalling or slipping

• Design a multi-threaded strategy for your target enterprise accounts

• Create a playbook to guide big deals from first touch to closed-won

Let’s land your next six-figure contract with confidence.

👉 [Schedule a call]