A live six-week cohort · 2026

Win/Loss
Foundations
in the Age of AI.

Winnable deals slip away by the smallest margins. Learn to turn buyer conversations into trusted intelligence — and become the person leadership trusts to explain why deals are really won or lost.

See what's inside

Your InstructorRyan Sorley, Author, Founder, Win-Loss Expert

20+years of experience across

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.

Watch · 80 sec

A quick look at what you'll build — in Ryan's own words.

Ninety seconds on why win/loss matters now, what this cohort is designed to unlock, and who it's built for.

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 Superpower
Use 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 Superpower
Turn 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 Superpower
Segment 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 Superpower
Beyond 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 Superpower
Cluster 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 Superpower
Turn raw findings into polished battlecards, executive summaries, and decks — fast.

What's Included

Everything you need to build the program — and prove it works.

Length: Six weeks
Format: Weekly lessons, live working sessions, assignments
Time commitment: 3 hours per week +/-
Materials: Recorded lessons and sessions, workbook, templates, AI prompts and instruction
Cohort: Small founding cohort
Credential: Win/Loss Hero Certificate

Meet Ryan

Hundreds of programs. One playbook worth teaching.

I'm Ryan Sorley, author of Blindspots and a win-loss practitioner with experience across hundreds of B2B programs.

I founded DoubleCheck Research, later joined Klue, and have worked with 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 better 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.

Order Blindspots on Amazon Or join the cohort →

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