Turn strangers into paying customers

Build the habits, skills, and confidence to pack your pipeline full of qualified opportunities and lose fewer deals you should have won
3,500+ reps and 100+ sales teams have used our programs to have their best sales months ever.
  • Jason's impact was evident, with a 135% growth in cold call meetings booked since we started working with him. If you want to boost your outbound sales efforts, Jason Bay is the expert you need; his training is smart, fun and impactful. I’d highly recommend him to any organization looking to level up their sales and BDR efforts.

    - Kelsic Pross, Director of Business Development, Navisite
  • When building out our SDR outbound team at Rippling, we shopped around for a variety of sales trainers, but were unable to find a solution that was TRULY tailored towards outbound SDRS - then we found Outbound Squad...Can not recommend enough!

    - Bert Brokaw, Director of Sales Development, Rippling
  • I can't recommend Jason highly enough for anyone needing outside expertise to improve their team's outbound selling capabilities... Excellent reviews from our team, and we've seen a quick tangible impact.

    - Cary Dunning, VP of Sales, Brooksource
  • I've had the pleasure of working with Jason at two separate organizations…During both engagements and after, we saw immediate results of improved prospect engagement, conversion rates, and confidence across the team. I highly recommend working with Jason.

    - Mark Wilchysnki, RVP, Harness

Is Outbound Squad right for you?

SDRs & BDRs

Level up your outbound skills to:

Build your confidence
Land more qualified meetings
Fast-track your path to AE
Our programs help SDRs/BDRs attain outbound mastery and prepare you to excel as an Account Executive
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Account Executives

Level up your sales skills to:

Self-source more pipeline
Run tighter sales cycles
Win more deals
Our programs help AEs master fundamental sales skills, build executive presence, and maximize their W2.
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Sales Leaders

Get help:

Upskilling your team
Standardizing a winning process
Driving repeatable outcomes
Our programs help enablement and sales leaders level up their rep’s skills through training, coaching, and playbook creation.
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Our Curriculum

Outbound Foundations
Discovery Foundations
Demo Mastery
Multi-Threading
Negotiations

Outbound Foundations

Build the systems, skills, and confidence to consistently pack your pipeline with qualified opportunities.
SDRs & BDRs
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

Outcomes

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

Outcomes

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

Outcomes

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

Multi-Threading

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

Outcomes

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

Negotiations

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

Outcomes

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 received a 3,300% ROI in my investment…”