I was Bored with SaaS. Until I Fell Down the AI Rabbit Hole.
How AI has re-ignited my spark for building in go-to-market
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Hey y’all! 👋
It’s been a minute since my last post here. I decided to pretend to be a European this summer and take a couple of weeks off (mostly), and when I got back, a few consulting projects got busy.
But, I’m here now, and have several posts that have been bouncing around in my head (and are half-baked drafts), that I’m excited to get out into the wild.
Today is one of those posts. It’s an idea that I’ve shared with a few people, and it seems to resonate.
So, I figured I’d share it publicly today — if nothing else, for the cathartic release.
And ideally, I hope it helps re-ignite the spark in a couple of readers.
Alright, let’s get right into it.
I was Bored with SaaS. Until I Fell Down the AI Rabbit Hole.
I was having a coffee with a friend recently and I (timidly) said: "I have been bored of SaaS—and running the same tired sales playbook—for the last few years."
He quickly nodded in agreement.
I went on to say: "But, AI has re-sparked my interest in SaaS over the last 12 months or so, as I've gone down the rabbit hole."
Every month, my conviction in AI grows that it will continue to become a more valuable tool for GTM teams to leverage over time.
My friend related it to "the excitement of the earliest SaaS days for me." And I totally agree.
The Same Feeling as Early SaaS Days
I haven't felt this excitement since the early days of SaaS. I first got into SaaS in 2013. I still vividly remember the first time the concept of SaaS—the magic of it (the scalability)—fully clicked.
It was over a coffee chat in Chicago, with Ari Shpanya. I would eventually, well, four days later, move across the country to share an apartment with him, and work at his company for the next three and a half years (this was my “Master’s Degree” in SaaS/go-to-market). Anyway, Ari explained the concept of SaaS so clearly and simply that it’s still embedded in my core.
He explained that “traditional” businesses (for example: service companies, retail, etc.) are fundamentally constrained. When they get a new customer, they need proportional resources to service that new customer. These businesses scale linearly: onboard a new services client, and eventually you'll need another account manager to handle the workload. Or: sell a widget and accrue x cost to produce said widget.
SaaS, on the other hand, scales exponentially. When you bring on a new client, you do not need to staff anyone else to support that client because it's software. I clearly remember him using the expression: “in SaaS, 1 + 1 = 3.”
This broke my mental model that I had had for the last 22 years.
Even though my first job out of college happened to be at a SaaS company, nobody had explained SaaS to me like this. Nobody made me care. Nobody had shown me the magic of SaaS.
Nobody had explained that SaaS was leverage.
Now, I felt like I had been given a cheat code to business. And, I would go on to exploit every area of this world for the next decade or so. Until the playbook became known, and tired.
The SaaS Burnout
If you're in SaaS and you're bored and you feel like you've been running the same playbook for half a decade now, it's probably because you have been.
I've been bored with SaaS for a few years now.
The thing that got me so excited back in 2012 was this point of leverage. And, that it was something new. Something unknown and under-explored. There was no playbook. We were all just figuring it out as we went along. That was fun to me.
In hindsight, it’s clear that the last few years have lacked that excitement. For me, that showed in my work. I wasn’t using my creativity. I was just doing the same thing over and over again. But, that has changed, slowly, but surely, over the last year or so. Thanks to AI.
The AI Awakening
Fast forward to today, and I have the same feeling as those early SaaS days. Maybe even more exciting! Because I’m aware of the rarity of this moment in time.
There have been 100 sparks that have penetrated my mind and I now see the world in a new way that I can't unsee.
History doesn’t repeat, but it does rhyme: AI is leverage.
AI enables me to scale my work in a way that makes “1 + 1 = 3”
I haven't felt this level of excitement (and intimidation/fear) since those early days of SaaS. I think, in part, because it is something new and exciting. It is uncharted waters. There is no playbook. We’re all just figuring it out together.
That, to me, is the most fun. It's about exploration, digitally. I'm not searching for a remote surf break or climbing up a waterfall to see what's around the next corner. But, it scratches the itch of exploring the unknown. Building, or finding, a trail that has little or no footprints yet.
Building Without a Playbook
Because there is no playbook yet, things are weird and wild and hacky. Experiments often fail. But the ones that succeed give you an advantage over your competitors. Finding this alpha is worth it when you have a lever the size of AI.
The old SaaS playbook may not be entirely broken, but it certainly doesn’t work like it once did. That’s because everyone knows the playbook. And, because there is more competition and noise than ever before. Things are simply harder today than they were five years ago. The bar to succeed has been rasied.
But, AI gives us a tool to get above that bar. It doesn’t come with a handbook or manual. We’re all just using it to see where it works and where it doesn’t.
In September of 2027, there will be a known AI x GTM Playbook. And then, it won’t work nearly as well as it will for the next 24 months. Being early will give you an advantage.
The Transformation Ahead
I have no idea what SaaS is going to look like in two years. But, I think it will look quite different. And that both scares and excites me.
The way we do sales, marketing, customer success, and operations will change a lot over the next 12 to 36 months. A lot has already changed over the last 12 months, which I didn’t realize until I went down the AI rabbit hole.
But the biggest learning for me is that AI is creating leverage. AI is creating something that wasn't possible 24 months ago. It's creating something that 99% of people don't realize is possible today, but it is.
You can do insane things and get incredible leverage with a sprinkle of creativity, a dash of thoughtfulness, and two handfuls of hard work.
Learning Through Experimentation
I'm no expert. In fact, I would say quite the opposite here. I'm still very early trying to learn. And publicly sharing what I learn. That is my goal with this newsletter: to share the things that I’m learning very openly and honestly.
I've said this before as well, but about 9 out of 10 experiments in AI that I run fail. That’s the reality of the current situation. I'm sure there are people that have a higher hit rate. But for me, that's about the outcome that I've seen in the experiments that I've tried.
I have to remind myself that if days, or even weeks go by where my experimenting does not provide a win, I have to keep going. Because eventually, there is a breakthrough that makes it all worth it. That win “pays back the fund” — 10 times over. Or, because of the infinite scalability of AI, 100 times over.
The Magic Moments
The best use cases for AI in GTM that I’ve found are specific to the business. But, when you find one, it unlocks a magical moment that keeps me coming back for more. Like a drug addict.
These moments might look like:
Testing a new prompt in an LLM that generates an answer that is as good, or frankly better, than what I could have written or discovered “manually.”
or
Speaking with Jason Lemkin’s AI bot for 20 minutes; then I go train my own, and it answers questions nearly exactly as I would (and even, sort of, sounds like me!).
or
Connecting two tools that unlock a new workflow that wasn't possible before.
or
Finding a way to categorize companies or people that is correct 99% of the time, and with the click of a button, works across 50k, or even 350k objects (okay, things break at the scale, but you get the point).
or
Building a scraper that finds certain data on a page and “thinks” (reasons) about that data to use it for account prioritization (ie: an intent signal).
These flickers of leverage get me stoked to continue to iterate and build the playbook of the future. A playbook that is not yet known, but is being written in real time.
Most of these creative ideas are found, not invented. My job is to listen to the top reps and leaders, curate the best ideas, experiment quickly, and then figure out how to operationalize and scale the winners.
The Future of Go-to-Market
I believe creative, thoughtful go-to-market will win in the future. And that excites me because that has staying power.
While “standard” signals get commoditized, the alpha will be in the nuance of each business.
AI and automation have, and will continue to, eliminate menial tasks and admin work.
I think AI will force most roles to evolve. Some will grow and expand, while others will become completely extinct.
I don't pretend to have all the answers. I'm just here to explore them. And, I'm excited to be exploring again.
A Moment in Time
This post is not about specific things to do with AI. I'm going to write that post soon, which I hope will spark some creativity.
Instead, this is something I wanted to write to stamp this moment in time, so that I can reflect on it in 10 years when I'm bored of running AI playbooks. :)
Just to know that there was a time when there was no playbook of how to use AI in GTM yet, where we were all just scrambling, running around, trying to figure this thing out together. Where 9 out of 10 of the things that we tried, failed. But that one that did work was magic. It gave us an advantage over our competition. It gave us leverage. It showed us that 1 + 1 can equal 3.
The Call to Action
If this resonates with you, that's great. And I'm excited to be on this adventure with you.
If the boredom of SaaS resonates, and you have not yet gone down the rabbit hole, I would encourage you to do it. Start with something small every day, or every week, that you’re excited to solve, and think AI can help you. You can’t read about it (including this newsletter); you have to personally play with it, hands-on.
This is the biggest wave of our time. This is not my words, but the greatest thinkers in technology are saying this.
I've seen a bunch of trends come and go over the last few years — PLG/PLS, signal-based selling, etc. I have a high degree of confidence that we'll still be talking about AI a year from now. It'll be the biggest topic, and we still will be trying to figure out the best playbook around leveraging it, and building with it.
Almost everything in SaaS is changing right under our noses as we speak. We overestimate what’s possible in a year, and underestimate what’s possible in a decade.
So, I'm hopeful that AI continues to re-energize other people who have been a little bored of SaaS over the last few years.
You have a nearly impossible number to hit and aren’t given any new resources. Look to AI. Lean in. It’s not a silver bullet. And, it’s hard. But, you won’t regret going down the rabbit hole. 🐇 🕳️
That’s it for today. I’m excited for a few more drafts to come to life in the next couple of weeks. Thanks for reading.
Quote rattling around in my head this week:
If you can see it (in your mind), and you have the courage enough to speak it, it will happen.
—Conor McGregor (the power of manifestation)
My favorite pieces of content I consumed this week:
Jessica Chiew of Canva on Building AI-Native GTM Org | The Revenue Leadership podcast with Kyle Norton
How Intercom rose from the ashes by betting everything on AI | Eoghan McCabe (founder and CEO | Lenny’s podcast
Scaling Agents Internally: Inside Atlassian's LEGO Block Strategy | First Round Capital blog
Re-read 1,000 True Fans (oldie but a goodie) | Kevin Kelly’s blog
A Cheeky Pint with Coinbase CEO Brian Armstrong | John Collison, Stripe Podcast
As always, thank you for your attention and trust — I do not take it for granted.
And, Happy Memorial Day 🇺🇸. I’m grateful to all those who served.
See you next time,
Brendan 🫡