This blog brought to you by ep. #356 of The Sales Hunter Podcast with Jason Bay.
Outbound Prospecting Has Changed—Here’s How to Win Now
On a recent episode of The Sales Hunter Podcast, Mark sat down with Jason Bay, CEO of Outbound Squad, to unpack what’s really working in outbound today—and how to fix the “broken math” of prospecting.
The Broken Math of Outbound
Cold calling isn’t dead—but the numbers have changed dramatically.
Jason Bay shared data from Gong showing that pickup rates hover around 5%, and only 5% of those conversations turn into meetings. That means it takes 20 calls to talk to one person and hundreds more to book a handful of meetings.
The traditional “more calls = more meetings” model no longer works. Instead, Jason advises treating your pipeline like a martini glass—narrow at the top, deep at the bottom. Focus on fewer, higher-quality prospects and go deep. Use business signals and trigger events to find people most likely to engage.
Quality Beats Quantity Every Time
Mark Hunter agrees: “You can’t make enough calls to fix bad targeting.”
Many CROs still push activity volume, but modern outbound requires precision. The best sales pros don’t chase everyone—they zero in on the right few.
Outbound success today is about smarter effort, not just more effort.
The Experience Gap: How Reps Can Get Better Faster
Fewer live conversations mean fewer chances for reps to practice. So how do you improve when you’re not getting enough reps in?
Jason offered three smart ways to build experience:
- AI Coaching Tools: Use ChatGPT or similar tools to simulate calls, refine messaging, and role-play. “You can literally practice voice chat with AI,” Jason says.
- Practice Prospects: Call “C-tier” accounts—those with lower potential value—to gain live call experience without risking big opportunities.
- Manager Coaching (in moderation): While manager role-play is valuable, Jason warns not to overload leaders with manual coaching tasks.
How to Stay Motivated in Outbound
Outbound is hard. Many new sales reps and solopreneurs burn out fast. Jason suggests starting with your “why.”
Work backward from your goals—how many deals, calls, and meetings do you need to hit your income target? Having that clarity gives your activity meaning.
Then, make it fun. Run power hours with your team. Share new openers and objection responses. “This isn’t an easy activity to do alone in your apartment,” Jason says. Team energy helps keep morale high.
Give Before You Ask: The Power of the “Offer”
One of Jason’s biggest insights: you need something valuable to give before you ask for a meeting.
He calls it “the offer.” Gong’s research shows reply rates jump 28% when an offer is included.
There are three kinds of offers:
- Sell the Blind Date: Promote a conversation with an expert or AE who’s helping similar companies.
- The One-to-Many Offer: Share industry benchmarks or analysis your company has done (like mystery shopping 300 e-commerce brands).
- The One-to-One Offer: Create a custom audit or mini-assessment specific to that prospect’s situation.
As Mark put it: “You’re delivering value. You’re going on the customer’s journey—not yours.”
Don’t Skip the Voicemail
Many reps skip voicemails because “no one calls back.” Jason says that’s the wrong mindset.
“The voicemail isn’t to get a callback—it’s a marketing message,” he explains. Point listeners to your email instead. Gong’s data shows that leaving voicemails can triple email response rates.
Even better, with AI call screening on phones, prospects are reading your message live as it’s transcribed. Make your reason for calling clear and relevant from the start.
Create Your Weekly Prospecting Rhythm
Outbound works best when it’s routine. Jason recommends a “weekly rhythm” built on habit stacking:
- Mondays & Fridays: Target selection and list building.
- Tuesday–Thursday: Daily call blocks—ideally in the morning.
If you’re new, ramp up slowly: one call Monday, two Tuesday, three Wednesday—until you’re consistently making 25–30 calls per day.
For seasoned reps, dedicate 90 minutes daily to outbound. “Eat the frog,” as Mark says—get it done first thing.
Top performers, they both agree, live by disciplined routines.
Outbound Isn’t Dead—It’s Evolving
Outbound selling today isn’t about blasting hundreds of calls. It’s about being strategic, consistent, and value-driven.
Mark wrapped up the conversation with this reminder:
“You can’t just call and ask for time. That ship has sailed. Deliver value—because when you do, you’re not interrupting someone’s day. You’re improving it.”
