B2B Sales School

A membership program to help SDRs/BDRs accelerate their path to Account Executive. And for AEs serious about leveling up their sales skills and income.
A Few Current Members
  • Jason and his team at Outbound Squad have many years of experience in B2B sales, this is evident in their process-oriented approach to helping sales professionals exceed quota. From my own experience, I've hit 200% quota as a BDR with their expertise and frameworks!

    Ming is on the fast track to becoming an Account Executive

    - Ming Fei Li, BDR at VMware
  • As someone who invests a lot of time into reading LinkedIn content and sales books, I have to say there has been nothing better than getting to work with a mentor to help put all the pieces together.

    Garrett joined Outbound Squad within the first 12 months of his sales career. During this time, he closed his first deal at $100k. His most recent win is closing a $258k deal!

    - Garrett Clifford, Account Executive at Praxent
  • Ana joined Outbound Squad as a BDR and finished in the top 20% of SDRs at Docusign. With our help (and a lot of hard work), she was recently promoted to Account Executive. Ana has a bright sales career ahead of her!

    Ana Capetillo, Account Executive at Docusign

Sales Is Tough Right Now

Prospects are becoming immune to cold outreach
 1/100 chance you get a reply to your cold email (Clearbit)
 1/67 chance of a positive outcome to your cold call (Gong)
Deals are taking longer to close
Sales cycles have lengthened by 40% since 2020 (Vendr)
Half of deals are lost to ‘no decision’ and status quo (Challenger)
Fewer reps are hitting quota
Only half of AEs are hitting quota in 2023 (Salesloft)
Quota attainment is down 5 points since 2021 (Iconiq Capital)
This economy is exposing sales teams who’ve relied on their brand, product, and a good economy to do the selling.
The B2B Sales School is all about helping you win by Focusing on the Fundamentals
Land meetings by focusing on problems
Product & feature dumping
Attach your solution to business priorities/problems
B.S. ROI calculators
Running engaging group calls
Boring buyers to death
Getting to power
Being "afraid to go over my champion's head"
Winning more deals at full price
Giving buyers all the control

Who is this for?

Account Executives

Who want to:

Grow their income to $250k+
Gain more executive presence
Master fundamental sales skills
Enroll Now


Who want to:

Accelerate their path to AE
Master fundamental outbound skills
Level up with other ambitious SDRs/BDRs
Enroll Now


Who want to:

Upskill their SDRs/BDRs and AEs
Supplement existing enablement and training
Address rep skill gaps
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Everything you get access to

Courses & Certifications
On-demand courses built for two primary paths: SDRs/BDRs looking to accelerate their path to Account Executive. And Account Executives looking to level up their skills, make their first $250k+, and get into President’s Club.
Office hours
Course content is great. But the real magic happens when you get help from our coaches to personalize the learning, hold you accountable, and help when you get stuck.
Monthly live workshops hosted by Jason and guest experts to help you implement the coursework. Show up ready to learn and engage. This is your chance to get personalized help and engage with our coaches.
Connect and network with a curated community of ambitious SDR/BDRs and Account Executives all looking to accomplish the same thing: level up their skills.

Our Curriculum

Outbound Foundations
Discovery Foundations
Demo Mastery

Outbound Foundations

Build the systems, skills, and confidence to consistently pack your pipeline with qualified opportunities.
Account Executives
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Learn How To

Run proven outbound plays to secure meetings with senior stakeholders
Cold calling: Use proven fundamentals to conquer call reluctance and secure more meetings from the phone
Cold Email: Use proven fundamentals to craft compelling email copy for double-digit reply rates
Self-source more pipeline as an AE
Use proven sequencing strategies to drive positive responses through a multi-channel approach


Help AEs self-source 30%+ of your own opportunities through outbound and increase pipeline coverage
Help AEs rely less on SDR and marketing support to hit your number
Increase the total volume of meetings set
Land higher-quality meetings that convert into qualified opportunities
Improve cold email and cold call conversion rates

Discovery Foundations

How to run sales calls that don’t feel like sales calls (and win larger deals faster)
Account Executives
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Learn How To

Open with strong introductions to stay in control to keep the call from going off the rails
Balance discovery vs. qualification so buyers don’t feel like they’re being interrogated
Find and attach to the buyer’s larger, company-wide business initiatives
Find business problems through carefully crafted questions
Secure next steps to build and maintain deal momentum


Larger deals
Increase in early-stage sales stage conversions
Shorter sales cycles
Increased forecasting predictability (knowing which deals are real and which ones are not)
Lose fewer deals due to status quo and “no decision”

Demo Mastery

Counterintuitive strategies to maintain control, secure next steps, and win the deal.
Account Executives
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Learn How To

Avoid common mistakes that buyers (especially executives) HATE
Plan and anticipate objections to customize demos for their buyers
Use the “Resonance Loop” to focus on key features that move the needle for the buyer
Running effective group calls to keep group engagement (while maintaining control)
Use demos to advance and move deals closer to the finish line


Increase late-stage pipeline conversion
Close larger deals
Lose fewer competitive deals


How to increase win rates by 25%+ (and never get stuck below the power line again)
Account Executives
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Learn How To

Reverse-engineer the perfect deal to build a repeatable process
Identify the right stakeholders to win the deal (and how to spot blockers)
Talk tracks to get prospects excited to introduce your reps to power
Plays to reps can run in their next sales cycle to engage senior stakeholders
Using multi-threading to free up “stuck” deals


Decrease # of deals lost due to lack of access to power
Increased forecasting predictability (knowing which deals are real and which ones are not)
Increased senior stakeholder involvement in deals


How to win more deals without lowering your price (and surrendering to your buyer)
Account Executives
Get Started

Learn How To

Never walk into a negotiation unprepared
Negotiate and win deals by countering with levers that don’t require sacrificing price
Navigate negotiations with confidence


Lose fewer competitive deals
Lose fewer deals late in the sales cycle
Close larger deals
Increased forecasting predictability (knowing which deals are real and which ones are not)
Improved rep morale through increased commissions and earnings
“I’ve hit 200% of quota with their expertise and frameworks!”

Enroll Today

What You'll Get
Interactive community with hundreds of reps
Access to Jason and our coaches
Monthly live workshops
Monthly live office hours
Outbound Foundations course
Discovery Foundations course
Demo Mastery course
Multi-threading course
Dozens of sales tools
For Individuals
Our goal is to re-launch this program in Fall of 2024. You'll get access to our entire course library, 1on1 coaching, office hours calls, a community of BDRs/AEs, and special guest expert sessions.

Join the wait list to get notified when enrollment opens.
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For Teams
Learn about custom options and tailored support for your team.
Contact Us