Enterprise Deals Made Simple

Let's face it - enterprise sales aren't always easy.

They're complex, slow, and involve multiple decision-makers.

However, here's the truth: mastering enterprise deals can significantly enhance your startup's growth.

I'll be honest. I've always loved high-activity sales cycles, quick closes, rapid deals, and small to mid-market accounts.

But having sold and managed my share of enterprise accounts, I've discovered a game-changing method: the Pilot Approach.

What's an Enterprise Deal, Anyway?

Enterprise deals are big, complicated 😅 and involve multiple stakeholders.

They typically don't close immediately, taking 6 months or more and involving amounts ranging from $ 50,000 to millions.

Large organisations prefer to test their product in a controlled way before committing fully.

Most of the time, that means closing small deals with small ACVS within large organisations, which results in no success.

That's where pilots come into play.

The Power of Pilot

A pilot is a smaller-scale implementation of your solution, focused on achieving specific, measurable outcomes before scaling up across the entire organisation - also known as a "wall-to-wall" rollout.

You start small and then expand the deal with a no-surprises roadmap to full-scale deployment.

Must-Have Roles in Your Pilot:

It is essential to have multiple people involved from your prospect/client side, like:

• Decision Maker: The ultimate project owner.
• Champion: The internal advocate for your product.
• Economic Buyer: Usually Finance, CFO, or Procurement.

Ensure these roles are clear from the start.

Document everything in a signed Pilot Agreement, along with the contract and its terms and conditions.

Structuring an Effective Pilot

Clearly define the scope and expectations upfront:

• Duration: How long is the pilot?
• Teams/Departments: Who exactly is involved? Why?
• Number of Users: Specify the number of users.
• Features/SKUS: Precisely what's being tested?
• Data & Reporting: Define how data is captured and reported.
• Support & Resources: Outline what support is available during the pilot.

KPIS & Tracking

Set clear, measurable key performance indicators (KPIS) that directly reflect your client's business goals.

Examples:

• KPI 1: Efficiency improvement (%)
• KPI 2: User adoption rate (%)
• KPI 3: Cost savings or revenue growth ($)

Regularly track and openly discuss these metrics with stakeholders to ensure transparency and accountability. Meeting these KPIS should directly trigger the full rollout.

Moving to a Full Rollout

Once the pilot proves successful, move forward decisively:

• Product Rollout: Gradually expand across additional teams in a structured and phased manner.
• Commercial Rollout: Transition smoothly from pilot pricing to enterprise pricing automatically, based on your signed agreement.

This structured process ensures there are no surprises or unnecessary renegotiations.

Why This Matters

Enterprise sales don't have to be slow or intimidating. They should be fun!

A well-executed pilot removes barriers, builds credibility, and creates a clear pathway to larger, faster deals.

Most importantly, stop wasting time on vague trials or unclear next steps.

Adopt a pilot approach, align with your stakeholders early, and close your deals with confidence.

Thanks for reading this far. See you all next week.