A live six-week cohort · 2026
Win/Loss
Foundations
in the Age of AI.
Winnable deals slip away over the smallest margins. In 6 weeks, learn how to unlock buyer intel that leads to higher competitive win rates — and become the person leadership turns to for the real story on why deals are won or lost. You'll do it all with AI in your corner, speeding up and scaling every step, from program design to insight delivery.
- •Founder DoubleCheck Research (acquired by Klue)
- •Cofounder and Head of Win-Loss at Klue
- •Author, Blindspots, The Ultimate Guide to Building a Better Win-Loss Program
- •VP Sales, Gartner and AMR Research; Seller at Forrester
The Program
A cohort built to be practical, focused, and superpowered with AI.
Each week you join a live group session with Ryan and a small cohort of fellow PMMs to work through a specific piece of the win-loss program-building process — then apply it through hands-on assignments before the next session.
You're not just learning from Ryan. You're building alongside other product marketers tackling the exact same challenge, at the exact same stage. Pacing, accountability, real feedback, and a peer group in the trenches with you.
Who it's for
Built for product marketers ready to own win-loss.
New to Product Marketing
Build your foundation and prove your value.
You're new to product marketing and want a clear, credible path to stand out. Learn the win-loss fundamentals that make you the go-to person for buyer intel — and show your organization the value you bring from day one.
- Establish win-loss as a core PMM competency
- Gain confidence talking to buyers and sales
- Deliver insights leadership actually acts on
Seasoned pros
Sharpen your tactical edge.
You've been around win-loss, but you want a more rigorous, repeatable system. Get the mechanics behind a program that scales — from recruitment to analysis — and use AI to speed up every step.
- Standardize program mechanics across teams
- Move faster with AI-assisted analysis and reporting
- Earn trust as the strategic win-loss leader
The Curriculum
Six weeks.
Six superpowers.
One Win/Loss Hero.
Each week unlocks a new AI superpower. By Week 6 you have the full toolkit to become your company's next Win/Loss Hero.
- 01
Readiness
Assess whether your organization is set up to support a win-loss program — stakeholder buy-in, data access, sales dynamics — so you're not building on shaky ground.
AI SuperpowerUse AI to audit CRM notes, call recordings, and past surveys to see what raw material you already have.
- 02
Objectives
Define what you're actually trying to learn, who needs the answers, and the metrics you're aiming to hit — so every step later ties back to a real business outcome.
AI SuperpowerTurn messy stakeholder input into a clear, prioritized set of research objectives instead of starting blank.
- 03
Recruitment
Identify and recruit the right buyers — wins and losses — and get internal stakeholders, especially sales, to cooperate instead of gatekeeping.
AI SuperpowerSegment your CRM pipeline for outreach and personalize recruitment messages at scale.
- 04
Data Gathering
Structure conversations that get past scripted questions and surface-level answers, so you're capturing the real reasons deals were won or lost.
AI SuperpowerBeyond transcription, explore AI-led interviews to scale your program's reach without adding headcount.
- 05
Analysis
Synthesize raw interview data into credible themes and insights — patterns that hold up to scrutiny, not anecdotes people can dismiss.
AI SuperpowerCluster themes across dozens of transcripts, surface patterns a human might miss, and stress-test conclusions.
- 06
Value Delivery
Package and deliver findings in a way that drives action — getting buy-in from sales, product, and leadership, and proving the program's ongoing value.
AI SuperpowerTurn raw findings into polished battlecards, executive summaries, and decks — fast.
Format
A 6-week rhythm that turns lessons into a working program.
Every week follows the same 3-step rhythm: learn the concept, workshop it live, then take action before the next session.
View recorded lesson
Watch a focused lesson from Ryan on that week's win-loss topic — the mechanics, the mistakes, and the AI shortcuts.
Join live working session
Join the cohort live to workshop real examples, get feedback, and leave with a finished piece of your program.
Complete Weekly Assignment
Apply what you learned through a hands-on assignment designed to move your win-loss program forward, week by week.
Time commitment
3 hours per week +/-
A flexible load designed to fit around a full-time PMM schedule.
Everything provided
Worksheets, templates & session recordings
You'll get every lesson, workbook, and template you need to keep building long after the cohort ends.
Meet Ryan
Hundreds of programs. One playbook worth teaching.
I'm Ryan Sorley, author of Blindspots and a win-loss expert with experience across hundreds of B2B programs.
I founded DoubleCheck Research, became the head of win-loss at Klue, and have worked at organizations including Gartner, AMR, and Forrester. Along the way, I've seen what separates a program that simply collects data from one that earns leadership trust and drives smarter decisions.
I created Win/Loss Foundations in the Age of AI to help product marketers, competitive intelligence leaders, and GTM professionals build that kind of program in-house.
The Book Behind the Cohort
Blindspots.
The Ultimate Guide to Building a Better Win-Loss Program. Written for teams tired of CRM reason codes, seller assumptions, and incomplete buyer feedback — and ready to build something leadership actually trusts.
- — Read the framework.
- — Apply the system.
- — Become the person leadership trusts.
Praise from the PMM Community
What leaders in product marketing are saying.
A wall of endorsements from the practitioners, founders, and operators who champion this work every day.
“So proud of my friend Ryan Sorley for launching this. If you care about win-loss done right, this is the book.”
Emma Stratton
Founder, Punchy · Messaging coach to B2B PMMs
“I remember the first podcast I heard Ryan on and thinking — this guy is the real deal. Blindspots proves it.”
Jason Oakley
Founder, Productive PMM
“Just added Blindspots to my GOAT book pile. The playbook competitive and PMM teams have been waiting for.”
Andy McCotter-Bicknell
Head of Competitive Enablement
“I've worked with Ryan Sorley for years. Nobody I trust more on win-loss — and this book delivers every bit of it.”
Elvis Lieban
Product Marketing Leader, Gong
“The best education does not cost $100,000. It costs the price of this book — and a weekend to read it.”
Hattie Brazeley
Hattie the PMM
“My guy Ryan Sorley had a huge week with this launch — and it's easy to see why. Required reading for modern PMMs.”
Mark Huber
Head of Brand & Product Marketing
“It's April 2nd, so no joke: this is the definitive guide to running a win-loss program that leadership actually trusts.”
Talya Heller
Founder, Down To A T
“Why do great companies lose winnable deals? Ryan's Blindspots is the answer — a must-read for anyone serious about win-loss.”
Gabriel Bujold
Product Marketing Leader
“Building an effective win/loss program isn't guesswork anymore. Ryan finally wrote the manual.”
Dylan D'Urso
Product Marketing Leader
“Congrats to Ryan on officially becoming the person the whole PMM community goes to for win-loss.”
Kimberly Bauer
Product Marketing Executive
“Baby Yoda wields the Force — Ryan wields buyer truth. Blindspots is that good.”
Eric Holland
Product Marketing Leader
“Big shoutout to my co-founder Ryan Sorley. Nobody has done more to raise the bar for win-loss than him.”
Jason Smith
Co-founder, DoubleCheck Research
Founding Cohort
Become your company's Win/Loss Hero.
No prior experience required. Seats are limited — applications are reviewed for fit.
Founding Tuition
$2,500
Reserve your seat
$500 deposit