Your pipeline looks like a desert, and the knee-jerk move is to spray more emails. More calls. More noise. But volume doesn’t fix bad targeting or lazy messaging—it just burns your list faster. Jason Bay (Outbound Squad CEO, coach to teams at Shopify, Zoom, and Gong) teaches a better fix: slow down, aim smarter, and only reach out when you have something worth saying.
His three-step play—prioritize the right accounts, craft buyer-first messaging, and thread it across your sequence—turns random activity into predictable replies.
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SALES
Never outbound a prospect before you do these 3 things
Your pipeline’s looking a little bit thin.
So what do you do?
Most reps just do more outbound to fix their pipeline problem.
100 accounts. 200 emails. 50 calls a day.
And the problem is… they usually still book 0 meetings because they’re targeting the wrong prospects or their messaging just frankly sucks!
Before you write an email, the #1 thing you need to fix is your targeting and your messaging.
Jason Bay, CEO of Outbound Squad has coached over 200+ sales teams (Shopify, Zoom, Gong, Rippling, and more).
These are the 3 steps he takes before sending a single prospecting touchpoint.
Prioritize The Accounts Most Likely To Reply
Craft Messaging That Actually Gets Your Buyer’s Attention
Weave That Messaging Across Your Sequenc
Part 1: Prioritize The Accounts Most Likely To Reply
Most reps think more prospecting activity equals more meetings booked.
When in reality, a spray and pray strategy is the quickest way to have your message deleted.
Instead, think of your pipeline as a Martini Glass, not funnel — narrow your focus to fewer prospects and target accounts that are most likely to reply.
Use Jason’s Hierarchy of Relevance to prioritize your prospecting efforts:
Persona: Who actually buys your product? Jason’s client sold to five roles, but marketing leaders were the only ones who actually bought anything.
Industry: What sectors have the best fit? This same client sold across many industries, but outdoor brands with physical stores converted fastest.
Company: What’s happening in the companies that buy? Even in the right vertical, a company with a leadership change was more likely to make a move today vs stick to status quo.
Individual: What’s going on in the person’s world when they buy? Execs respond to company-level relevance (like strategic objectives) while managers respond to personal context (like what’s painful about their personal role).
Part 2: Craft Messaging That Actually Gets Your Buyer’s Attention
Most reps think they’ll land meetings by cramming every reason to buy their product into their messaging.
When in reality, prospects want to hear that you understand the problem they’re trying to solve — before you ever talk about the product you sell.
Use Jason’s 4-Part Messaging Matrix to build messaging that speaks your buyer’s language:
Priorities: A CISO is measured on one thing above all else — reducing risk — so open your outreach by speaking directly to the priority your prospect actually cares about.
Current Solutions: If a team is managing security alerts in spreadsheets, that’s their current reality — so reference how they do it today to show you understand their world.
Problems: Those spreadsheets and manual workflows mean no real-time visibility and higher exposure to threats — so use that to show you understand their world.
Aspirations: A CISO ultimately wants to walk into the boardroom confident they’ve lowered risk and secured the environment — so close by painting that future state in a simple, credible way.
Now we can use this to build a message that actually lands!
Part 3: Weave That Messaging Across Your Sequence
You might already know that a good outreach sequence includes 10-14 touches over 3-4 weeks across multiple channels (phone, email, Linkedin).
But most sellers hit prospects with the same message over and over and over again.
Jason creates different outreach angles using the Keep It Simple Sequencing (KISS) framework.
Each messaging block in the KISS framework includes:
Day 1: Email + Call + Social
Day 3: Call + Bump Email
Create 2-3 messaging angles across your sequence using the messaging matrix:
Week 1: Messaging Angle 1 (Reducing cybersecurity risk in spreadsheets)
Week 2: Messaging Angle 2 (Reducing cybersecurity risk from phishing)
Week 3: Messaging Angle 3 (Reducing costs of litigation from fraud)
This allows you to test multiple problems on a single prospect.
And that’s a wrap folks!
HEADLINES
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That’s all for today.
Until next time,
Team B2B Whales
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