⚡️ Today’s level up ⚡️
Today’s edition highlights how I thought differently as a strategic seller and the impact that made in transitioning to do my own thing on my terms.
Let’s go!
Read time: <7 minutes
If you missed last week, read it here.
A unique perspective
The biggest catalyst to improving my sales performance and accelerating my path to retiring early from the corporate world came from a company that doesn’t even believe in employing a single salesperson.
Let me share the full story.
The Background
A huge leap in my sales career came when I made the jump from Enterprise Account Executive at Revel System to Strategic Account Director at LivePerson back in 2018 (both in SaaS).
I went from selling an iPad-based point-of-sale solution at a company that focused primarily on SMB customers but aspired to break into the enterprise space. At the time, they defined enterprise as brands with 100 locations or more.
However, at LivePerson, they were a public company that had 25 years of history and was designed for the enterprise from the get-go. They defined enterprise as brands with 5,000 employees or more, and further, my focus was on a specific list of 50 strategic new logos across North America, all of them in The Fortune 500.
The results of that move were profound. I achieved the following within four years:
– Made life-changing income in the millions of dollars
– Worked with transforming iconic, global brands
– Promoted to VP with the autonomy of an IC
– Able to retire from corporate life early
However, the first 24 months in the strategic role was a grind.
I was still subscribing to the rules peddled by “hustle porn” bros:
– “You can rest when you die”
– “Go big, or go home”
– “Growth at all costs”
– “Wake and grind”
But that all changed in the middle of 2020…
The Catalyst
After the initial shock and awe of Covid slowing down the world, I went deep within.
I no longer wanted to define my self-worth by status symbols (like leaderboards). I wanted to become more purposeful with my decisions. I desired my work to feel like play.
This internal exploration coincided with being asked to spearhead a future of work initiative at the company called “Project Beehive.” (A contributor to my love for the 🐝)
About 100 volunteers from our 1,300-person company were asked to re-design how our company needed to work as a fully distributed, asynchronous-first workforce, all while I still carried the largest quota in the company.
It was a lot to manage, and I needed a different way to think and operate to make both endeavors successful.
The Discovery
To manage Project Beehive, we chose to deploy a project management tool called Basecamp.
It’s made by a company called 37signals. Their name comes from a catalog of ideas – signals – that drive their business ethos. And you guessed right, they have 37 of them. You should check them out.
When I researched the company, my eyes were opened to a new way of operating that felt very natural to me.
For reference, the company has been around since 1999, and they:
– Have no salesforce
– Have ~75 employees
– Have 100K+ customers
– Have no plans to go public
– Have no investors, no board
– Never want to sell their business
– Make over 8-figure profits each year
– Have made a profit for 24 years in a row
They run circles around much larger, VC-backed businesses with 15 – 30x employees in terms of efficiency and profit margins.
How is this possible?
I dove headfirst into learning about their unique perspective and approach by studying their principles, reading their books (Remote, Rework, and my favorite, It Doesn’t Have to Be Crazy at Work, and listening to their co-founder on podcasts (like this one).
The main takeaway from what I discovered is that the popular rules for growth aren’t the only ways to grow. Being purposeful about doing less can actually lead to better results and healthier margins. Not to mention, feeling more satisfied.
The New Path
For the remainder of 2020, I redesigned my work from the ground up.
I started tracking everything that I was doing and using Thrive Space to become more insightful and intentional with my work. I had long ditched goals in favor of systems, but for the first time, I started to define my “anti-goals” – things I wanted to do less of. I also got more intentional about designing my calendar around deep work.
In It Doesn’t Have to Be Crazy at Work, they talk about building a “calm company.” One that was sustainable – basically one that was work you’d want to do for life on your terms.
Although I had long-term ambitions to do my own thing, just a few months prior to Project Beehive and discovering 37signals, I was totally fine continuing the fast-paced life as a top-producing strategic seller.
However, the forced slow-down of a global pandemic and an introspective period connected me with what I knew was true in my heart. That slow is fast.
I started reading more. I started writing more. I started sleeping more. I started tracking more.
All of these purposeful actions allowed me to understand better what was truly important to me and how I wanted to begin designing my work around my life – not the other way around.
Like 37signals, I started to define principles that were important to me. Like 37signals, I wanted to focus on less (fewer accounts) and deliver more (bigger profits). Like 37signals, I needed to ditch crazy and become more calm.
And the results told me that this new way of operating is the better way:
First 24 months at LivePerson (2018 & 2019):
– 78% win rate
– 5 new logos acquired
– 7 new opportunities won
– Deal cycle average was 7 months
– $11M in ARR delivered
– Averaged ~5 hours of sleep per night
– Worked on average 10 hours per day
Second 24 months at LivePerson (2020 & 2021):
– 78% win rate
– 6 new logos acquired
– 7 new opportunities won
– Deal cycle average was 6 months
– $16.3M in ARR delivered
– Averaged ~7 hours of sleep per night
– Worked an average of 6 hours and 40 minutes per day
Analyzing this from a pure performance basis, my win rate and the number of new logos and opportunities stayed roughly the same. However, my deal cycle shortened, my deal size increased by 48%, my sleep increased by two hours per night, and my time worked dropped by over three hours per day.
By treating myself like a “calm company,” I was able to slow down and deliver more.
Were there macro events at play? Sure, but they worked against me, not for me, like other SaaS sellers benefited from during 2020 – 2022. Because I was focused a lot on the travel and hospitality industry, that industry got decimated when Covid hit. In addition, my pipeline had been completely depleted at the end of 2019.
But, working more deeply, focused, and calmly were key factors to the change. I eliminated the things that didn’t serve me because I became hyper-aware of them through strategic commitments I put on my calendar each year, month, week, and day.
Besides the quantitative improvement, I saw a big qualitative improvement as well. My fitness improved because I was sleeping better and had more energy. My relationship with my wife improved because I was less irritable and working more consistent hours. Those things are priceless in the game of life!
Lastly, because I was doing more reflection and writing, I was able to launch my side business as a project, give it attention, and accelerate my path to solopreneurship (By the way, the 6 hours and 40 minutes per day of work included the side project work).
The Invitation
Why am I telling you all of this?
I’ve spoken with many of you, and I know you, too, want to enhance your sales performance. You have many reasons for doing so – to find more time with your family, to start investing in real estate, to launch your own business, to do your life’s work…calmly.
You’re a contrarian. You’re different. You’re purposeful.
I get you!
But I also know what the chaos is like because I’ve been in your shoes just a few short years ago.
Whether you’re coming off the biggest year of your career or one of underperformance. The chaos right now is the same. You have a new year with a new number on your head. It’s back to 0, and it’s a grind to do it all over again.
But I invite you to take some time before you head into Sales Kickoff this year to reflect on what’s important. Decide what you no longer want to do and design a better way to work and live.
In fact you must, because this way of operating is proven to deliver results and improve your life.
If you need help along the way, you know where to find me.
See you next week!
Here’s how I can help you right now:
1 | Unlock the 7 Figure Seller OS
Learn how to use design and systems thinking to become a 7 figure seller. There are 3 options to allow you to customize your learning journey.
2 | Download The 7 Figure Open Letter
Get the creative strategic selling strategy that landed a $5.9M deal with a top 4 major global airline. Bonus inside!
3 | Book a 1:1 coaching session right now
You can book a 60-minute coaching session with me (although the Pro above option provides access to 1:1 coaching with me at a 70% discount.