The Uncharted Territory Holiday Spectacular
2025 themes, recommended reads and more!
tl;dr - Some reading material for your holiday downtime (if any):
A personal note
Themes to watch in 2025
A (clearly premature) best of list
Some recommended long reads
An invitation to Uncharted Coffee
—
Every revenue leader I know has a love/hate relationship with the holidays. On the one hand, you’ve got the most wonderful time of the year filled with kith and kin. On the other hand, you’re knee deep in the 4th iteration of the plan and your team still has 12 deals in play.
We worked with our teams to get their deals in early to avoid just this situation. Yet here we are. Of course, Christmas falls on a Wednesday this year. It’s the worst! Some signers may even (gasp) take the whole week off! Surely we can at least get a signature on Friday the 27th or Monday the 30th, right? Right??
So we’ll spend our family time with one eye on our phones checking for that Docusign, stepping away from dinner to take a call from a panicked rep or texting that VP who’s skiing in Vail to see if she can please review that final redline.
It’s part of the job. Some of us hate it. Some of us thrive on the pressure. Some of us need the excuse to step away from Uncle Ted’s opinions. Some of us don’t have or don’t want the family time.
Inevitably, though, the holidays do have a bit of downtime so I’ve put together a slightly different format this week. I’ve sprinkled in some 2025 themes, a best of list and some long read recommendations. Kind of the GTM newsletter form of a variety show—aka the Uncharted Territory Holiday Spectacular.
As for me, I spent a good portion of the week after last Christmas at my Mom’s house in what was once my sister’s childhood bedroom1 on Zoom calls with some particularly prickly lawyers and an obstinate CFO. I told myself I was annoyed but there’s also a part of me that loves the chase.2
This year I want to do it a bit differently. I’m 44. My parents are getting up there. I’m lucky to still have them both. They’re divorced but we still get together as a family. They get along fine. They dote on their granddaughter. We carry on some the traditions that date back to when I was her age. There will always be more deals but there won’t be an infinite number of these Christmases. I’m going to do my best to be present.
I’ll be back with another issue on January 8th. Thank you so much for reading. May you celebrate the season in the way that’s best for you and yours. And may those 12 deals that are still in play all close smoothly.
— Hayes
Themes to watch in 2025
I haven’t reached full pundit brain yet where I really think you want to hear my predictions for the upcoming year. However, I do think there are some GTM themes worth watching in 2025:
Things are better but teams will stay small
The year of pricing experimentation
Slow(er) outbound makes a comeback3
Let’s dig in.
RIP bad times, but also big teams
There are reasons for optimism about the economy (fed rate cuts, incoming extremely pro-business policies) but plenty of reasons for caution. Markets are pretty frothy and inflation is pretty stubborn.
However, after one bad year (2023) and one ok year (2024), everyone’s tired of being tired. Lots of companies have made real structural changes to get more efficient and there’s a new tech paradigm to rush headlong into. It’s time for some IPOs, for sales cycles to compress a bit and for CFOs to be a little more lenient on spending.
However, hiring—especially in sales—will lag way, way behind these other things. The era of massive sales teams to drive growth is over (unless you’re Salesforce, see below). The lessons of the past couple years, combined with the judicious use of AI, are going to mean each individual seller can be vastly more productive.
The great pricing experiment
Ok, that thing I said about massive sales teams? The rules may not apply to Salesforce. Marc Benioff is hiring 1,000 2,000 humans to sell AI. Those lucky humans are going to sell it for $2 per conversation and make Salesforce the largest provider of “digital labor” on the planet. Bold moves from the guy who bought his very own chunk of Hawaii with the proceeds from selling seat licenses.
Most SaaS pricing still rests on a simple idea: when more humans access the software, you charge more money. In the past few years we’ve seen certain products move to usage based models (especially in the developer ecosystem)4. AI, however, takes it to another level.
Is AI replacing humans? Augmenting humans? Something else? Regardless, we can’t charge for seats anymore. This confusion is leading to new pricing efforts—generally aimed at charging for outcomes, not access. Kyle Poyer wrote a thorough discussion of this possible transition that’s well worth reading.
This is a great time to experiment with pricing models. You may well stumble on something that works better for you and your customers. I don’t know where it’ll end up, but I do predict that the good ol’ seat license will take a very long time to die.
Slow outbound
It’s no secret that outbound has been stupid hard the past few years. Mostly the response has been to arm the spam cannons and just do more, hoping to squeeze enough meetings out of those 0.05% reply rates. Throw in AI SDRs (and their lies), and it’s miserable to be on the receiving end of this as a buyer. No wonder outbound is perpetually dead.
Where do we go in 2025? We can either absolutely blanket the world in outreach or slow down (a little) and make our outreach really, really good. Jason Lemkin touched on this in his closing remarks at SaaStr—even advocating for the 1 hour email:
Research 100 prospects who truly need [your core capability]. It will take time and it will take more time that just putting in a csv into a tool and using a lookalike audience (which can work to some degree too) but this will almost certainly boost opens if you’re confident that who you’re pitching too has a need for your product.
Spend an hour crafting each email. Yes, an hour. Yes the AI SDR can do hundreds per hour, but most have noted they haven’t closed a single deal yet from an AI SDR. Zero x Zero is still zero. So take the extra time to craft highly personalized outbound.
Aside from my quibble with Jason’s use of “personalized” in the quote (relevance always beats personalization), he’s right. I’ve been harping on these same topics quite a bit. Get fanatical about building your target account list and get super relevant with your messaging, especially with references to existing customers.5
Technology-wise we can either a) make AI SDRs so good that it doesn’t matter that they’re AI or b) use AI to give humans everything they need to do great outbound. I believe in the latter. A truly good account allocation mechanism gives reps the bandwidth to write one hour emails, while a truly good research mechanism makes those emails take less time. Winners in 2025 will figure out how to use “proof of human” to set themselves apart.
Best of Uncharted Territory
Uncharted Territory has only existed for a couple of months but that’s not going to stop me from doing a “Best Of” list!
Are You Behind in AI? - I read a bunch of the GTM AI surveys so you don’t have to. Learn about the current state of GTM AI adoption, use cases, AI spending and where budgets are coming from.
The 3+1 ICP - Win more often by simplifying your ideal customer profile into 3 universal dimensions + 1 unique factor (or factors) specific to your business.
Pipeline Lessons from Vertical SaaS - Vertical SaaS can teach all of us how to generate more pipeline. Learn how these companies nail relevance, build a target account list and systematize account coverage.
When Growth Cools, CROs Feel the Heat - The average CRO lasts just over 2 years but companies that replace their CROs usually struggle. Learn what to do if you’re in the hot seat.
Are You Really Covering Your Territories? - See how to quickly diagnose if your reps are actually working your territories and what you can do if they aren’t.
The Outbound Bottleneck - When outbound isn’t working, we usually try to fix activity and messaging. The real bottleneck? Your account strategy makes relevance impossible. There’s even math to prove the point.
I’ve thoroughly enjoyed writing this newsletter each week and deeply appreciate everyone who takes the time to read and share. I want to make sure I’m writing about the things that matter most to revenue leaders so please let me know if there are topics you’d like me to cover in the future.
Long(er) reads
If you find yourself with enough time to do some more serious reading, here are some books (and one long blog post) that I found worthwhile this year.
Templeton Compression and the Sales Ready Product - Before we had PLG, Don Templeton made a career of figuring out how to compress sales cycles by turning the product into a weapon that quickly wins over decision makers.
Boyd: The Fighter Pilot Who Changed the Art of War by Robert Coram. - John Boyd was an ace fighter pilot, accidental aircraft designer and a brilliant military strategist. He developed the concept of the OODA loop which revolutionized the US military. I gave a talk about OODA loops for CROs at the Pavilion CRO Summit in June.
The Elements of Style by William Strunk and EB White. - Also known as “Strunk & White” this is a tiny book that will make you a better writer. Among other things, you’ll never want to say “leverage” or “utilize” again. Bonus: stick “Use Strunk and White style” in your ChatGPT custom instructions and you’ll get more concise and direct responses.
Invention and Innovation: A Brief History of Hype and Failure by Vaclav Smil. - It’s always helpful to remember that we don’t actually know anything as we live through hype cycles (cough, AI).
Krakatoa by Simon Winchester. - It’s an engrossing history of the eruption and its myriad impacts. The thing that most stuck with me is that the world of infinite real-time information we live in today started with an absolutely insane web of telegraph lines. Those lines allowed an eruption halfway across the world to quickly make headlines in the West.
The Goal by Eliyahu M. Goldratt. - Look, this book is weird—it’s a “business novel” where the protagonist saves his marriage and his factory through the magic of lean manufacturing techniques. But if you want to really understand how to make any linear process more efficient (like, say, a sales pipeline) it gives you all the tools you need.
Upcoming Uncharted Coffee Events
This year, I'm curating 10-person coffee meetups with VP+ revenue leaders in cities across the country. We do these Jeffersonian Style—one single conversation for the whole group where everyone gets to participate in a discussion of topics that actually matter to running a revenue org.
We held first one in Chicago earlier this month with some amazing leaders who gave it high marks. Below is the schedule so far. If you’re in any of these cities and want to join the conversation, please register!
My childhood bedroom is now an office, but that office was occupied by a 7 year old on an air mattress.
I got ‘em done though! Got one on the 29th and one on the 31st. Thank god for great champions.
After all, slow is smooth and smooth is fast.
Usage-based pricing has helped make it possible for Jeff Bezos to spend $1B a year on the scenic route to space and for Frank Slootman to achieve godlike status in enterprise SaaS.
Astute readers might say, “This is just ABM!” And they’d be pretty much right.