Issue #79

Enterprise Sales Engagement Plan

This week I am going for the jugular, let me know if this hits for you, I appreciate your feedback on what you like.

This is a five step plan for getting into a medium to large company, based on 15 years experience doing it for DHL.

And 10 years having it done to me, when I was in ops and procurement.

Objective: Get into a targeted account, position your solution as high-value, and drive the deal to close.

Step 1: Qualify the Account Properly (No Wasted Time)

Most enterprise sellers waste months chasing bad deals. You need to know three things before engaging:

1. Find out if they have budget.

Check job postings (hiring in a department = spending in a department).

Look at public financial reports (growth = money to spend, decline = money problems). Unless you specifically help companies with finance issues, steer clear of the second type.

Ask: How do you typically evaluate and fund initiatives like this? (If they can’t answer, there’s no budget.)

No budget means you will have to get them to create one, which adds another quarter (at least). That means the go int he low priority list.

2. Find out if they have a real need.

Search for pain signals (new regulations, competitor pressure, leadership change).

Ask: What’s stopping you from hitting your next big goal? (If they struggle to answer, no real need.)

3. Find out if they’re open to change right now

Ask: The last time you brought in a new solution, what drove that decision?

If they can’t name a clear trigger, they are change resistant and you’ll waste time.

We know how I feel about wasting time…

If they say it was a CEO mandate, find out if that CEO is still there and how to get to them.

Step 2: Get in at the Highest Level Possible

Reality: If you start with middle management, you’ll spend months educating, only for the project to get vetoed by someone higher up.

Get a warm intro (if possible).

Use LinkedIn: Who in my network knows someone at the target company?

If not, find a customer or colleague who used to work there and ask them for intel.

If no warm intro, force your way in with value.

Don’t send a generic outreach email. Instead, attack a specific problem:

[Industry trend] is killing [companies like yours” here’s what’s working instead. (Attach a great case study if you have one.)

Call: I’ve worked with [Company A] and [Company B] on solving [specific challenge]. You’re likely thinking about this too, worth a quick chat?

If stuck at a lower level, don’t stay there.

Ask: How does your executive team view this challenge?

If they dodge, ask: Who has final sign-off if we find the right solution?

If they refuse to connect you, assume they are blocking the deal (they are not a real champion).

Step 3: Control the Buying Criteria

If you let an incumbent supplier define the criteria before you arrive, the deal is already lost. You need to shape the criteria in your favour.

Introduce a missing metric.

Example: If they’re focused on price, shift them to long-term ROI or time related savings.

Say: Most companies I work with start by looking at cost, but they realise the real problem is [X]. Have you looked at it this way? X is a factor that goes deeper than cost, such as profit erosion, customer retention, product fit or a business model weakness.

Turn their existing process against them.

Example: If they’re using Excel instead of automation (yes, it is still rife), ask: How many hours does your team spend on this per month?

What happens if that person leaves, who owns the knowledge?

Frame your product as eliminating risk & inefficiency.

Control the framing in competitor comparisons.

If a competitor is in play, don’t attack directly, instead, reposition them as out of touch.

Say: They do a good job for companies [bigger /smaller] than you, but don’t really know how to handle your particular needs. What’s your take?

Step 4: Make it Easy for Them to Say Yes

Enterprise deals die when the buyer feels the decision is too risky or complicated. You need to make it easy for them.

Offer a no risk start.

Pilot: Most companies start with a 90-day test before rolling out. That work for you?

Phased deployment: We can start with just [one department /business unit/ region] then roll out to suit your own pace.

Remove internal friction.

Find out who will lose out from the deal or who’s life will be made less convenient by the project and get them on board asap.

If procurement are involved, find out what process they say they have to use. Then get it in front of your customer coach and let them deal with it with you. They will most likely keep them happy for you.

Give them a simple decision.

If they hesitate, say: We can tweak X or Y, but otherwise, this is a strong fit. Should we move forward? Let’s schedule the steps.

Step 5: Close & Lock in the Account

Winning the deal is just step one, you also need to defend the account from competitors later.

Get a signed agreement with a kickoff date - letters of intent and award notices are not legally enforceable.

If they agree but delay signing, say:

Let’s lock in the agreement so we can hold your spot for implementation and funding from your side.

Immediately schedule a “success plan” meeting.

Get them to commit to the first result to hit in 90 days?

Expand the deal.

After success, active contract management can optimise the profitability of the relationship by finding cost savings, further roll outs and upselling additional services.

What Makes This Plan Work?

You’re qualifying hard early (so you don’t waste time).

You’re going straight to decision makers (so deals don’t stall).

You’re controlling the criteria (so competitors don’t frame the sale).

You’re making the decision easy (so they don’t feel overwhelmed).

If you want to know more about how your buyers think, try this:

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In the meantime, remember to copy and paste this into your next presentation to your boss, it will get you promoted...

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If you are ready to take a step up in your sales career I can help - you can get my foundations course here or drop me a line to discuss personal or team based projects to increase your revenue.