The Uncharted Territory Summer Extravaganza
Crack open a cold one and catch up on some sweet GTM content.
It’s unseasonably cool here in Austin. We’re barely cracking the mid 90s. I’m used to hitting a string of 100° days before we end Q2 and start making adjustments for the 2nd half.
Temperatures aside, those mid-year adjustments are plenty familiar. The plans put in place during the cold winter and launched at SKO have now gotten punched by reality. That, combined with summer slowness, makes July a time reflect, reevaluate and adjust for sales teams.
I might as well do the same for Uncharted Territory.
I started this newsletter last November. Since then I’ve published 32 weekly posts and it’s grown to just over 1,500 subscribers.
Beyond the numbers, I’m proud of the content. Several of you have taken the time to personally reach out and share when something lands and I deeply appreciate it. I may not always hit the mark, but these words are pure, unadulterated human effort. In a world overflowing with AI slop, that counts for something.
Thank you so much for reading.
Given that many of you in the States will be OOO enjoying the long July 4th weekend, I’ve got a different format today to help while away any downtime between grilling and fireworks. Here’s what you’ll find:
Some new ways to use Uncharted Territory content.
A short survey to help me make this newsletter better.
A round-up of posts that seem to have resonated with folks so far this year.
Read on for more.
Get more from Uncharted Territory
This is a pretty basic newsletter for CROs—I’m not exactly running a media company over here. That said, there are a few other ways to experience the magic that is Uncharted Territory.
Ever wanted to chat with all this content? No? Well too bad, now you can! I collected all my posts, interviews and presentations into NotebookLM and made it freely available. It’s a smarter way to search, summarize and contextualize stuff I’ve shared.
If you’d prefer to skip the AI and chat with me directly, hit me up on LinkedIn, Substack chat or come to one of our events. There’s also a YouTube channel with interviews and a few public talks if that’s more your thing.
Help me improve
It’s really awesome that folks seem to be enjoying the content but I want to see if we can take this whole thing up a notch. I’d really appreciate it if you would take this short survey so I can make this newsletter as useful as possible.
Some summer reading
I have no doubt that all of you read this newsletter the moment it hits your inbox and never, ever, miss an article. But in the event you’re a normal person who does not do those things, I thought I’d share a few posts that seem to have had an impact. A long July weekend might be a good time to let some H2 ideas percolate.
Pipeline, pipeline, pipeline
We had our best Q2 ever at Gradient Works. One thing that’s helped us immensely is a revised approach to pipeline coverage.
We went all in on the recommendations from Dave Kellogg and Paul Stansik that I talked about earlier in the year. We’ve been using that approach to help us track pipeline and set our forecast. As a result, we’re much better at calling our shot.
There’s more where that came from. See below for posts about pipeline coverage, measuring pipeline production and diagnosing pipeline problems. Interestingly1, 3 Outbound Metrics CROs Need is my top post of all time according to Substack.
ICP, accounts and territory
We’re heading into Q3 with a record amount of pipeline. I hope you are too. In case it helps, one change we made at the beginning of 2025 was to dramatically shrink our universe of prospect accounts down to a target account list of about 600 accounts.
We focused on a few core ICP attributes and then used AI (+ some manual effort) to get to the ones that weren’t simple firmographics. Naturally we managed these using small, focused dynamic books and high-quality human outbound.
See below for a few articles that describe the approach we’re taking—one that’s working for us and many of our customers.
AI and the 10x Sales Rep saga
Back in May I published The 10x Sales Rep. It was my attempt to reverse engineer what would have to be true to for AI to turn a “classic” mid-market SaaS rep on a $1M quota into a $10MM quota-carrying machine. It went viral on LinkedIn and garnered quite a lot of feedback—some of it positive, some of it… not.
Since I’d clearly struck a nerve, I decided to turn the whole thing into a talk at the Pavilion CRO Summit in Denver.
The conference was super interesting and a great opportunity to hear how 150 CROs are thinking about the big changes underway in sales. I shared what I learned in a post called Are CROs OK which quickly become one of my top 3 most viewed.
Finally, AI in general has been a huge topic. It’s impacting everything from day-to-day work, to how teams get structured to the future of RevOps. Below are a few articles that dig into those topics:
What I’ll be reading
There are lots of great GTM folks sharing wisdom with the world. Dave Kellogg’s Kellblog is a must read. If you’re an operator—especially in PE—you should be reading Paul Stansik’s Hello Operator. Kyle Norton has amazing interviews with sales leaders. And, if you want to understand the (slightly) more technical side of AI in GTM, you should check out Brendon Short’s The Signal.
Enjoy the 4th. 🎇🇺🇸🎇
To me, at least.