Welcome to the Weekly Wrap-Up, where I share interesting links and thoughts from the past week.
Before we jump in.
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Dynamic Range
The path from $1m - $50m ARR is a graveyard for sales leaders.
The average tenure for CRO / VP of Sales is under 18 months.
You almost never hear of the same sales leader leading a company from $1m to $50m+.
Why is it so rare for sales leaders to level up as the company scales?
The "$0 - $1m" sales leader struggles to get to $10m.
The "$1m - $10m" sales leader struggles to get to $50m. And so on.
You see so many examples of this across the B2B SaaS industry.
I struggled with this throughout my career as a sales leader.
My path from first sales hire, to Head of Sales, to VP of Sales, to Chief Revenue Officer is uncommon.
It took 10 years to get through all of that growth, but it all happened at one company: Levelset.
I don't know any other sales leaders who have experienced a similar career trajectory to the one I experienced.
Even the best leaders tend to jump to new opportunities within 3 or 4 years, for one valid reason or another.
So why was my experience at Levelset an exception to this rule?
I was lucky. I had a CEO that believed in me and invested in my growth.
Of course I had to meet half-way and build my skills. I also had to chase the number, grow revenue, and provide a ton of value to the company and its culture.
I was able to grow my skills and leadership ability to to level that the company needed.
I've heard this trait called "dynamic range" and I believe its crucial for early stage execs across any function.
It helped that the executive team around me was filled with other leaders who had the same dynamic range. They were pushing themselves to grow and learn in the same way.
Let's be clear, I probably could have been fired or could have left for another opportunity many times throughout the 10 year journey.
But I didn't get fired. I didn't leave. I never even looked for a different opportunity, seriously.
I just kept leaning into the opportunity with Levelset, trusting the team around me and trusting my CEO to make good on our commitment to each other.
And it worked for me. It's one part luck and who knows how many parts hard work.
I'm a totally different person and professional than I was when I started my career in sales leadership.
From playing jazz to playing in an Orchestra
Working in an early stage company is kinda like playing jazz.
Everyone member of a jazz band has their speciality, but the music comes from how they improvise and push each other to play.
As you scale, the company looks more like an orchestra than a jazz band.
Each section of an orchestra is highly specialized.
The music is structured to blend each section together to make a sound - a symphony.
Sure, a jazz player can learn to play in an orchestra. But it is rare.
In the same way, the $0-1m sales leader can learn to be the $10m or $50m leader.
But this kind of personal growth is uncommon.
It requires a level of self-awareness and a commitment to learning that most people don't have.
It also required dynamic range - the ability for a leader to improve their skills to match the stage of the company.
When you have a leader on your team who shows dynamic range, invest in them.
Give them the opportunity to learn how to play in an orchestra.
- B2B SaaS is in trouble
What's going to happen to all the SaaS companies?
I'm paying close attention to the topic lately, because I believe the industry that I built my career in (B2B SaaS) undergoing a sea-change that will impact how I should be investing my time and money.
AI is driving down the cost to build software.
Companies (like Klarna) are opting to build internally instead of renewing their licenses with Salesforce and Workday.
Tom Tunguz recently posted a new essay today about the challenge to SaaS orthodoxy:
"How good of a CRM could a software company build with a $10m annual budget & with AI?"
Sam Lessin and the crew at Slow Ventures have been talking about the end of the SaaS era for a while.
"If you can build software today that allows you to operate basically any 'real world business' 20% - 30% better than it is operated today, use that leverage and take over those businesses... take the wins, get the growth, use the margin expansion to dominate your competitors in the actual business."
Hard to know where this leads to over the next 10 years, but it's sure to be different in many meaningful ways.
Who else is talking about this? Where can I learn more?
- A Manifesto by Sir John Hegarty
This year I have been working on getting better at copywriting, advertising, creating content, and creative marketing.
I've gone down the rabbit-hole of copywriting luminaries like the Boron Letters, Ogilvy's Confessions of an Advertising Man,
I've even taken copywriting courses like Copy That. I read from modern copywriters like Creative Samba and Marketing Examples.
This week, I came across this poster inspired by legendary ad man Sir John Hegarty. It's a manifesto, or a set of rules to inspire you.
Some of my favorites:
#2 Remove the Headphones - the world is full of inspiration. Listen.
#4 Read Shit - Read good things in the hope it will rub off. Also
#6 Respect, Don't Revere - Admire ideas, not people. They don't let you down.
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Have a great weekend!
Martin
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