This Move Paved The Path To Earning $1M+ In SaaS Sales

⚡️ Today’s level up ⚡️

Today’s edition outlines an important and purposeful decision I made at the start of my Strategic SaaS sales role that ended up providing a wealth of insights. I turned these insights into $3,843,695 in personal income from 2018 – 2022.

Let’s go!

Level up from Enterprise to Strategic

I joined LivePerson, a leader in Conversational AI, in January 2018.

It was my first time entering strategic sales. I had previously been an Enterprise Account Executive at a late-stage startup for a few years.

It felt like I was entering the Premier League (for any English footy fans out there), so I wanted to make sure I hit the ground running.

In today’s edition, I want to share where I focused my time, energy, and attention in the early days.

I’m glad I did because it created the blueprint for earning a life-changing income in a relatively short period of time and set me up to retire from the corporate world for good.

Find, study, and interview the innovators

Before joining the company, I had provided my old employer with notice in late December. That gave me about a month to decompress from my old role and start getting ready for the new one.

Besides putting out some strategic updates to my network that could be leveraged in my new role, I spent a lot of time reading through the top case studies. I studied them like an MBA student would absorb business cases in order to pass a course.

The one that caught my attention the most was T-Mobile, as the timing of that partnership had materialized a few years prior and LivePerson had a strong foothold inside that brand.

It was an interesting case study because it was the most transformative. Even Harvard Business Review documented their journey, which gave me an eye-opening perspective that directed how I would go about acquiring new business during my four-year tenure there.

What the HBR article gave me was a perspective beyond LivePerson’s own internal case study. Did Marketing give us that, sure, but this was extremely valuable for three key reasons:

1. It didn’t just talk about how T-Mobile used LivePerson’s technology. It outlined the complete transformation of their contact center and how the entire business benefited from that initiative.

2. It highlighted the results, the risks, and the blueprint of how they did it.

3. It singled out the leader inside the organization that led the transformation (Callie Field).

The third point was particularly valuable to me, as, at the time of my hiring, the company was focused on persona-based playbooks. We could talk to those in Customer Service, Marketing, Sales, eComm, IT, and even HR.

A lack of focus is actually a burden that could translate into wasted time and lost money, so I had to be careful.

In addition, I was hired to be a net new logo specialist (along with five other new recruits). Our job was to sell $250K “starter packages” to land the business, hand it off, and allow a Client Partner to expand the business.

I had other plans.

To enable my strategy, I needed to think bigger and, more importantly, get my prospects to think bigger while focusing my attention on the right type of accounts and personas to pursue.

Studying the T-Mobile business case in obsessive detail did just that.

→ I had an ideal persona (heads of Contact Centers)

→ I had a big idea (focus the company around transforming the contact center)

→ I had the plan to do it (create a “Team of Experts” model)

→ I had credibility (T-Mobile went from worst in customer service to first with healthy profitability)

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The cool thing was I wasn’t leading with or talking about our technology. It simply came along for the ride. This perspective allowed me to operate and talk more like a consultant from a major firm, like Accenture or Deloitte.

It also made it easier for me to design a better buying experience (versus blindly following a self-serving sales methodology). Instead of leading with a simple use case (aka the $250K “starter package”) or a drawn-out sales cycle where I spent months trying to discover pain, I knew clearly who I needed to talk to (Contact Center leaders) and what they needed/should aspire to do (create their own Team of Experts model).

My job was to gauge where prospects were very early on: Are you a big innovative thinker who wants to do something bold like Callie Field at T-Mobile and build a legacy? If so, game on. If not, so long.

This maniacal focus made my job infinitely easier, more enjoyable, and more lucrative!

Here’s how to find them

I was fortunate that LivePerson put on amazing customer events where we invited prospects to learn from customers who were doing interesting and innovative things using conversational AI. This one in New York happened to occur during my first week on the job, and I was entranced.

It inspired me to sell new business through the lens of our most innovative customers, as these were the types of engagements I wanted to be a part of.

Maybe your company doesn’t put on intimate, white-glove customer events. But that doesn’t preclude you from stealing a page of out of this playbook. You just have to know where to look and what to ask.

Where to find them:

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