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Selling to Executives

Don’t Start at the top!

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Here’s proof.....
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Best Practices
1. Systems Integrators should always be involved in large technical deals.
2. Bring a CS into the implementation phase and assign one during the sales cycle
3. There should be an SOW written highlighting which milestones you are planning on hitting based on company goals. Highlight how you typically do implementations. Something that speaks to the prospect based around what they want accomplished by which dates and who will be involved.
4. Find a way to unearth insights and shed new light on high priority problems and quantify the impact they can have on a customer’s business. It can take weeks to come up with a single value prop for a new prospect because you have to do lots of research.
5. Get executives involved early - beginning of the sales cycle. You need to get the engagement of the company’s top brass.
6. Prove value early to avoid a small deal
7. Suggest Proof of Concept, Proof of Value to justify the large investment the customer needs to make to achieve the desired result
8. Avoid procurement commoditizing you and driving the price down by developing relationships with key stakeholders during the sales process

Crushing your Exec Meeting


Community Wisdom

David - “Prep a ton, try to find 2-3 compelling narratives you know they will care about. Pretty easy for public companies, harder for private. This is where prepping with a champion to understand that executives hot areas is key.
Then very early on set the table with why you are there, story on outcomes driven other places, the business opportunity for them, and then gain their perspective on what a successful call would look like for them. Then proceed to deliver that call.”
Nate Nasralla - “First, the pre-meeting must-do’s.
1/ Write out a compelling narrative with your champion.
Focus on bigger priorities like:
- Seismic shifts in an industry
- Looming and existential risks
- Massive, untapped opportunities
If the exec isn’t intrigued by a high-level narrative, they won’t go
deeper on how to operationalize it (with a product).

2/ Cut your full narrative down to a 2-sentence soundbite.
3/ Follow the 25% rule for material prep. Materials should take
roughly 25% of the meeting’s time, to let execs go off agenda.
4/ Lock down the exec whisperer’s support. One of a few
people who hold a "no-questions-asked" level of trust.

5/ Attach a short memo to your invite as a pre-read.
- Set the calendar invite to start at :05 after. -
Attach a 1-page business case to the invite.
- Let their EA know there's a pre-read in the invite.
- Join the call at :05 after and dig in together.
It tees you up to drive toward what's most important.
Not every exec will be a fan, so check with an assistant or your champion.

Now, a minute-by-minute guide during the meeting.
(:00 - :05) Deliver a Non-Obvious Insight
Earn and hold their attention by sharing something like:
Most believe ___, but actually, ___. Your pre-read can help here.
(:05 - :10) Adapt to Their Quirks
Every exec is a little odd in their own way.
They develop a style of working over the years. Understand and adapt to this.
:10 - :20) Correct or Confirm Your Narrative
Secure feedback on your core message. They’ll either: (1)
Confirm what resonates, or (2) Correct what they disagree with.
(:20 - :25) Frame Up the Decision Path
Execs think in terms of choices & tradeoffs. Your risk is they
prioritize an altogether different project over yours.
Do they believe the cost of the problem you solve / its payoff
is greater than the cost / upside of competing priorities?

Last, two steps to follow-up on your meeting.
1/ Send a forwardable email. Exec-level meetings kick off a
bunch of internal communications you want to help shape.

2/ Use No-Response-Needed Updates:
“< Executive >, we’re continuing to make good progress on X.
We also have Y planned next week, and will update you after.
No reply needed here — just keeping you in the loop.”

John - “My prospects are software engineers and developers, so from their perspective the get little value from talking to sales people. Often times they flat out don't like us.
But, here is the value in talking to me that even resonates with them:
I talk to people in their position everyday, hearing the challenges they face and how they overcome them.
The software I sell is something new to them that could potentially help them. At a minimum, they will learn something new or confirm that what they are doing today is the best option”
Nathan - “I use a "value-based sales" approach. So, by the time I'm on the CXO's calendar I've hopefully had a meeting with some of their reports to quantify the size of the problem they're having and the size of the proposed solution. Most of my solutions are providing $1M + in value per year, so my $100k price tag seems reasonable.
But if I haven't done that work the price tag can seem high. If it's the first meeting, then I use the "Nobody cares how much you know until they know that you care" approach.
I use the first meeting to let them tell me what problems they're having in my space, and I use it to do the quantification. Then I get to the end and let them know I'm going to work on the $xxM problem they have and get back to them with a solution in the next two weeks.”

Executive Discovery Questions

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Must have an OTE of $200k+

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