Vol. VI ★ No. 27 Austin, Texas ★ 2026–27 Edition

Drew Crichton

Today's Feature The Rep Who
Went Upstream
Austin, Tex. B2B SaaS Since 2020
★ At a Glance ★

Six years carrying a quota. Now I build the strategy behind it.

I spent six years in B2B SaaS closing the deals marketing teed up, and learning exactly why they closed. Now I'm building the go-to-market strategy upstream of the call: who to target, what to say, and how to prove it worked.

Seeking: Product Marketing & GTM Strategy roles · May 2027

Selected Work

Case01Fall '26
Social Enterprise vs. an Unmapped Market

Goodwill NYNJ

Leading go-to-market for a mission-driven security-staffing venture: who buys, why, and how to sell to them.

4Sectors segmented
Read the Case →
Case022026
AI vs. the Empty Funnel

Squire

Put AI to work on research and segmentation so the prospecting got sharper, not just louder.

+30%Top of funnel, MoM
Read the Case →
Case032020–22
Field Marketing vs. Sales Silos

Rackspace

Analyzed 300+ commercial accounts and got field marketing and sales aiming at the same ones.

$400K+Pipeline generated
Read the Case →

Career at a Glance

★ Career Numbers ★
6+
Years in B2B SaaS
5
Companies
120%
Best Year vs. Quota
50+
Enterprise Accts Managed
Year-by-year results
CompanyRAXRPTRSQTHRSQR
Years'20–22'22–23'23–24'25'26–
Result$400K110%104%101%120%

Point of View

Column · AI in Marketing

AI Made Outreach Cheap. That Makes Strategy Expensive.

At Squire I used AI tools to lift top-of-funnel activity about 30% month over month. Here's the part nobody puts in the press release: when anyone can generate a thousand "personalized" emails before lunch, the email stops being the advantage.

AI can write the email. It can't decide who should get it.

The advantage moves upstream. Which accounts are actually worth it? What can we say that's specific and true? What would prove it worked? Those are segmentation, positioning and measurement questions. They get more valuable as execution gets cheap.

That's the bet behind my pivot. I've watched the downstream get automated from the seat of a quota-carrier, so I'm moving to where judgment still decides the outcome.

How This Program Was Printed

I built this site with Claude Code, directing an AI agent the way I'd brief an agency: the concept, the copy, the edits. It's plain HTML, CSS and a little JavaScript, deployed on Cloudflare Pages. I shipped it at 70% and I'm tuning it as I go, the way marketing actually works now.

One More Thing

A Firmly Held Opinion

Pineapple Belongs on Pizza and Should Not Be Controversial.

After careful review, the ruling is in. Sweet against salty isn't a stunt. It's one of the most proven pairings in food: salted caramel, kettle corn, chicken and waffles.

The Hawaiian pie has been selling since Sam Panopoulos put canned pineapple on one in Chatham, Ontario, in 1962. Six-plus decades of repeat purchase is not a fad. The product was never the problem.

The positioning is. Add jalapeño, call it "sweet heat," and watch the complaints stop. No further appeals will be heard.

RuledFinal · No Appeals