Nobody gets fired for buying IBM.

Problem: Two Champions In Every Deal

We all tend to approach champion-building in our deals with blinders on. Focused only on OUR relationships and not the competition’s.

While helpful for racehorses, who can be distracted by their almost 360-degree eyesight.

It’s not a winning strategy for us.

We need to see the entire field, not just our running lane.

Any deal you’re working on has at least two champions:

Yours & your competitor’s.

But when selling against a Goliath⚔️, you typically face 3+ champions in their corner.

Not just the direct buying team, but also ALL the other people who used the ⚔️ product at previous companies and now work at your prospect company.

A real Jon Snow against the Bolton Army situation.

“But why do they buy the way more expensive tool when we do the same stuff for less?”

All things being equal, consider this:

It is so much safer for champions to just buy the market leader when it’s time for a final decision.

The risk of execution is lower & crucially, the risk of their job security becomes obsolete.

As the old saying goes: “Nobody gets fired for buying IBM.”

So how do you combat that as the Underdog? That’s what we’re tackling today.

Storytime

One of these buyers was nearing a renewal. Their Initial concern: price.

One of these buyers was nearing a 1st purchase. Their initial action: demo with the market leader.

Running this play got me in the door with many reps on the teams.

A few lunches. A little bit of texting. A decent amount of volume.

End result? Rep-level-champions. An ARMY.

Other impacts? Slack messages saying:

“Have you heard of Pickle? You should talk to Junior”

“Junior messaged me today, I was waiting for it to happen!”

My personal favorite: “Check out this cold-call script Junior sent me today. I’m gonna try it.”

I aim to have at least 20+ connections at every company on my target account list.

Prospect Company #1: Nearing Renewal

Prospect Company #2: Nearing 1st Purchase

Solution: Build an Army with ‘The User Gap’

A few market leaders got product-led growth ‘right’ early-on (Calendly, Grammarly, Slack).

But most big players over-emphasize sales efforts directed toward the same buyer level: The Decision Maker

Elite tech companies are built to maximize revenue by appeasing the contract signer. Leaving a huge gap: The End Users

Startups recognized the power of strategic focus on end users. Building better design & experience, ease of use, and faster time-to-value.

Allowing us Underdogs to build an army leveraging what we call ‘The User Gap’.

For this play, a social platform like LinkedIn is your best friend.

The sole goal is to directly message end users.

Seriously. At one account, I messaged 58 reps - not joking about building an army.

Drop them a connect with a note - here are three templates I use:

Here’s some real messages using these templates in the wild:

Insights & Additional Thoughts

Thought #1 - Entire companies were created to take advantage of The User Gap. Think Scratchpad vs Salesforce, Canva vs Adobe, Notion vs Google Docs. Market leaders as a platform are better positioned for decision-makers. Dig in & make the User Gap known. Decision makers want a happy team.

Thought #2 - When you message users, 1/4 won’t ever see it, 1/4 won’t accept it, 1/4 will accept it, 1/4 will accept & reply. It’s a numbers game. That’s the rule of thumb I live by.

Thought #3 - A VP after signing told me, “My team would’ve been pissed if I chose a different software. You did a great job. They are actually excited about the new tech.” Users have a voice too, make sure you help them use it.

Thought #4 - Before you message users, try to find the right ones. That could be tenure in role/company, listed accomplishments, # of mutual connections. The first message I ever sent landed in the DMs of a top rep, as indicated by quota attainment listed on his LinkedIn. From there, he helped me snowball.

Thoughts #5 - After you’ve had positive engagements with users, use their name in future engagements. If you drop more DMs, mention that you talked with other Users (AKA their peers).