You’re not the one-pager person. You’re the GTM point guard.

Alley-Oop is a monthly newsletter for solo PMMs at Series A and B companies. Every edition covers one real situation we’re up against and how to handle it from 3 different angles: relationships, tactical execution, and enablement.

First one lands November 2nd. Unsubscribe anytime.
Not a Solo PMM but think "ICP" means Insane Clown Posse? You will fit right in.

// You’re in good company

Solo PMMs at companies like these read Alley-Oop.

  • Vector
  • Goody

// What’s inside

What’s on your plate (and mine).

The problems I’m solving right now, so you can borrow the answers.

  • Dig past “can you make this 1-pager?” to what’s really going on
  • Figure out which PMM type you are: strategic, tactical, or enablement-led
  • Win over [redacted] leaders first: every other relationship gets easier after that
  • Write launch SOPs from the ground up, so launch day stops running on vibes
  • Set a consistent GTM meeting cadence to avoid those “per my last email” Slacks
  • Create a shared brain for your commercial team, so you stop being the answer to every “where’s that doc?”
  • Stand up a closed/lost analysis program on the fly, before someone asks why you’re losing
  • Launch an MCP when nobody has written the playbook yet
  • Map out an AI skills roadmap your team will actually be excited about
  • Start a customer program from scratch in a highly regulated space (and survive legal review)

What Every Month Looks Like

Each edition works one problem you’re fighting right now, using my own experience and the vetted PMMs I tag in, so you get what worked and skip what didn’t.

Example: launching an MCP early adopter program, in three moves.

  1. Internal alignment

    Same page, then early adopters

    Everyone agrees on the plan, and your best customer accounts are using it before launch.

  2. Set expectations

    Release isn’t launch

    Realistic pipeline goals, and a team that knows shipping from launching.

  3. Enablement

    Build it once, hand it to everyone

    Customer-facing, technical, and enablement resources your team uses without you in the room.

// Money-back promise

If a month falls flat, let me know.

Each edition gives you at least one move you can run by the following Friday. If one doesn’t hit, tell me why. Alley-Oop is VoC-driven, so what you say shapes the next one.

  1. You reply
  2. I listen
  3. Next edition gets better

// Shout-outs

These PMMs run it back with Alley-Oop.

“Know that friend whose notes you borrowed in college because they paid attention in class and deeply cared? That’s Adam, but now he’s sharing his notes for product marketing. He should find a new hobby to relax after work, but instead he’s writing a newsletter. Crazy? Yes. But do I want those notes? 100%”

Drew GiovannoliFounder, Buried Wins

“Every solo PMM deserves a work bestie. Adam just volunteered for the job (take him up on it).”

Tamara GrominskyFounder, PMM Camp

“Adam’s playful, very human take on the stress of being a founding PMM makes his content the kind you actually look forward to.”

Shannon KearnsPMM Consultant, More Than Said

“Adam does a fantastic job of guiding the conversation - pulling out the best nuggets from his guests’ lived experiences without the extra fluff…”

Allison RonaDirector of Product Marketing, Petdesk

“I met Adam on multiple Zoom calls. He’s not AI – he’s the real deal.”

Zach RobertsFounder, Scope & Sequence

“Adam’s content feels like an HR-approved PMM side-hug.”

Suz KochSolo PMM, Goody

Stop taking requests.
Start running the offense.

We respect your privacy. Unsubscribe anytime, but only after a fridge cig.
Never make big decisions on an empty can.

Adam O’Brien, founder of Alley-Oop, smiling at the camera
  • 5×Built PMM from scratch
  • FoundingPMM Camp guide
  • 4thplace, Marketer of the Year, Greater Tampa Bay Area, 2017

What’s good. I’m Adam.

I’ve built product marketing from scratch five times, which means I’ve been the PMM team, the enablement team, and the person asked to “just put together a quick one-pager” enough times to be considered unstable.

Fifteen-plus years, seed to PE portfolio, and I’ve run enablement for GTM teams from 1 to 250. Alley-Oop is me writing it all down so you can skip the “learning it the hard way” part.

// Outside work

  • 3x dad
  • Vintage millennial
  • Sneaker head
  • Serial podcaster
  • Long-suffering Kings, Giants + Niners fan

// The last shot

Get the playbook to win as a solo PMM

One email a month. Each edition breaks down one real situation and gives you a move to run by Friday.

1st one lands November 2nd. Unsubscribe anytime.
Oh yeah, it's positioning then messaging.