️ ️⚡ Today’s level up ⚡

Today’s edition focuses on insider insights from the top 1% producers who never have a depleted pipeline in strategic sales.

Let’s go!

A better place to set up camp

From January 2018 - June 2021, I won sixteen deals that generated nearly $30M per year in annual recurring revenue (ARR).

Want to know how many of those deals I sourced myself?

Only two.

They also happened to be my first two, and they were critically important to set a new paradigm in my strategic sales approach.

Before we get to that, a little warning! My position will disappoint a lot of people in the sales community. That’s because most sellers fall into two camps:

Camp 1: Think SDRs should source their opportunities for them.

The idea is as they progress in their career, opportunity creation is a function outsourced entirely to the sales development team.

“Why should I do the grunt work?” is the leading thought.

Camp 2: Think, as Account Executives, they should source the majority of their own opportunities.

The idea is that top producers need to find their own opportunities so that their pipeline never runs dry.

“Why would I entrust my pipeline and commissions solely to SDRs?” is how they think.

Sadly, both of these perspectives are dead wrong.

That is if your ultimate goal is to enter the seven-figure annual earners club and own your future on your terms.

There’s actually a third camp reserved for the top 1%.

The majority of opportunities are actually sourced from their executive team.

They’ve put themselves in a position to be the number one trusted resource with their executive team.

“Why wouldn’t I work on the most important opportunities for the company?” is the mantra.

Here’s the secret the top 1% have tapped into

There are massive opportunities that land on the desks of your C-suite all the time.

If they don’t land in your lap, then I hate to be the bearer of bad news, you fall into Camp 1 or 2.

But being in the prestigious Camp 3 is not about luck, politics, or playing favorites, it’s a game of strategy.

The very top performers in sales have amplified their pipeline generation by always being the go-to resource when executives are greeted with an opportunity that comes across their desk.

This is because executives need to have a high degree of trust that their reputations will be protected and confidence that the opportunity will close.

Let’s break down a proven pathway to creating this persistent reality.

The path to landing priority projects and opportunities

Here are five ways to be thought of first when a large opportunity comes across the desks of your executive team. These are especially helpful when you’re starting fresh in a strategic sales role inside an organization.

1. Operate differently

When I was hired as a Strategic Account Director at LivePerson, my job responsibility (along with five others) was to sell $250K “starter packages” to land new logos on our strategic account list and then hand them over to Client Partners to expand the relationship.

These were single use case programs meant to accelerate deal cycles. However, the challenge I saw with this motion was that to successfully navigate, position, and architect an MSA with a Fortune 500 company, it was going to take some time. I wanted that time to have a higher payoff.

Besides, leading with a $250K “problem” would box our company into solving small challenges for their company and limit us to having more transformative-level conversations with their C-suite.

I chose to buck this trend and instead focused my whole approach in showcasing an expansive and broad transformation that could be had (in phases) using our technology.

This achieved three optimal outcomes:

• Increased the ACV potential for net new logo deals

• Created a new blueprint to position our tech to new logos

• Improved our ability to connect higher up in the org, accelerating deal cycles

In my first year, I was the only seller on the team to meet their number by closing two exciting deals I sourced directly through my existing network. This was valuable proof to our executive leaders that when it came to new logo opportunities, my unique positioning was a better strategy.

2. Move fast when others are slow, and slow when others are fast

Speaking of those two opportunities, they were foundational for opening the door to the executive team because I manufactured them entirely on my own.

I certainly didn’t close them on my own (that took collaborating effectively as a team, which I’ll touch on later), but I did generate one through my existing network and the other through an open letter approach that leveraged my extensive experience as their customer.

To achieve this, I took full advantage of the downtime between my old role at a different company and this new role to accelerate pipeline generation by:

• Contacting my network where new opportunities could be harvested

• Learning the product deeply, and more importantly, studying key case studies​

• Prioritizing my accounts and strategizing on creative outreach approaches I’d deploy

The mindset here was that while my peers and company would be intentionally moving slow to onboard, learn, and get acclimated, I didn’t want to waste any time moving straight into having real business conversations with prospects.

This played out nicely in my favor, as when conversations with new logos started happening at the top, they had to be assigned to sellers to nurture. Who do you think they thought of when this happened?

Because I proved my talk track and understanding of the solution was the more advanced than others on my team, within my first ninety days I was already speaking to Aramark and Delta (which I had sourced) as well as Apple (through IBM), Facebook, and American Airlines (assigned by my leaders).

This purposeful decision to move fast out of the gates paid off to accumulate real-world experience with massive brands, land two opportunities, surpass my number, and then get more intentional with who I worked on and move at a slower pace in year two.

3. Enlist the help of your CEO early

I was fortunate to have a hands-on CEO who volunteered to help with strategic deals (as long as we came organized and put him in a strong position to help).

In both of the first-year wins, I pulled him in as a strategic asset. This helped forge a strong relationship by:

• Showcasing my ambition

• Highlighting my interest in large, strategic deals

• Building rapport and learning from his deep experience

A bond was forged over thinking big. This helped me later when Covid hit, and after coming off a strong year in 2019, my pipeline got shaken up because it was centered around accounts that had been hit hard by the pandemic (travel and hospitality).

Yet, when an opportunity arose to develop a net new product (at-home testing powered by Conversational AI) for an existing account, I was the first person the CEO thought of to lead the strategic sales initiative. That opportunity led to several more that landed millions in ARR.

4. Keep your executive team updated often with timely updates

I’m a big fan of writing as a key skill to uplevel all other sales skills. This holds true for keeping your executives up to date on key opportunities (and where you want to go next in your career).

Here’s a five-part story framework you can use (verbatim) from my friend Nate Nasralla of Fluint:

1/ In the Beginning:

Lead with a truth your buyers agree on. A priority they’re already sold on.

Then, describe their current reality in a way that feels crazy accurate.

One that shows that you “get it,” and deeply understand their context and core values in a way others don’t.

2/ Turning Point # 1

Start contrasting “what is” vs. “what could be.”

Make sure the difference between these is as wide as possible.

Your job is to create desire with an exciting vision of the future, then show how your ideas fill that desire.

3/ Middle:

Your storyline has to raise the stakes here.

What’s it all for? Why not just keep living life as it is?

Then continue to alternate what is / could be / is / could be, etc. Constantly creating and resolving tension in your emails, business cases, wherever you’re delivering your message.

4/ Turning Point # 2:

Make a clear call to action. What should people do? Beyond just “signing the contract,” what’s required?

Continue to outline the reward that’s waiting for them if they do.

5/ Ending:

Recap the big idea, and create a sense of calm confidence.

Not all of us see ourselves as strong writers.

So, if you need a little guidance while planning the broad strokes to your storyline, to guide how you craft the rest of the narrative behind your deal, check out this worksheet:

5. Build a reputation as a cross-functional friend

One thing I’ve found executives love more than closed/won deals is your ability to work collaboratively with other departments to close those deals. Don’t burn bridges. Build them.

To do this effectively, know who the specialists are (and do it early). Who’s the master at explaining integrations? Who can explain what’s exciting on the product roadmap? Who’s the mad scientist who geeks out on large language models?

Everybody wants to be a part of the key deals for the company, so pull them in and respect their time and contributions. Like writing an effective narrative update on the progression of the deal, take the time after a deal has closed and post it to the deals Slack channel calling out each individual’s contribution to the win.

When you build a strong reputation with others, they’ll share with their leaders how enjoyable it was to help close the account and work with you. During ELT meetings, this gives your name more chances to percolate to the top as a consistent thread to the best and most exciting opportunities happening inside the org.

That’s a wrap for now. See you next time!