May 28, 2026

Why Follow-Ups Lead To Sales – Ep. 29

In this episode of Prospecting Pros, John Karsant talks to Dillon Tucker about his transition from finance and insurance sales to SaaS, SDR leadership, and fractional growth consulting. Dillon shares his early mentorship experiences at Outreach that sparked his love for coaching and developing sales talent. They talk about the common mistakes SDRs make and Dillon says that bad follow up is often the biggest reason opportunities are lost. He explains how prioritizing prospects, eliminating friction and making scheduling easy dramatically improves conversion rates. Dillon also talks about the importance of multi-channel prospecting via phone, email, and LinkedIn, while adjusting to evolving buyer behaviors. The episode wraps up with practical advice on asking better discovery questions, building SDR programs from scratch, and how sales professionals can stand out by focusing on genuine curiosity, empathy, and solving real customer problems.

Real conversations. Proven strategies. Sales that scale.

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The LevelUp Podcast brings you insights from the front lines of B2B sales, outbound strategy, and pipeline growth. Whether you’re a founder, sales leader, or startup builder — we break down what actually works in modern prospecting. Brought to you by LevelUp Leads — a B2B Sales Development agency helping businesses land more meetings through done-for-you outbound. We act as an extension of your team with Fractional or Full-Service SDRs, tech-enabled outreach, and the kind of expertise that builds real pipeline.

🎧 Learn from industry pros, proven playbooks, and behind-the-scenes takes on cold email, LinkedIn outreach, and cold calling — all designed to help you generate more conversations and revenue.

Some of our guests:

Scott Leese

Sales leader, consultant, and founder of the Surf and Sales Summit

Featured on:
Building From Zero With Scott Lease – Ep. 19

Jason Bay

Founder of Outbound Squad

Featured on:
Door Knocking, Grit & B2B Sales Mastery | Jason Bay on Coaching Top Teams – Ep. 20

Justin Michael

Author of Cold Call ALGO and longtime sales innovator

Featured on:
The Future Of Sales In The Age Of AI – Ep. 12

Josh Roth

B2B sales leader

Featured on:
Building a Career in Sales From Zero to Top BDR Manager – Ep. 16

R.J. Jalichandra

VC & PE-Backed CEO

Featured on:
Leadership Lessons From 6x Venture & PE-Backed CEO – Ep. 17

Chris Ritson

Founder & Sales Trainer

Featured on:
Navigating the Risky Jump from SDR to AE – Ep. 26

Podcast Episodes:

Simplify And Scale Your Sales Team – Ep. 11

July 9, 2025

On this episode of Prospecting Pros, host John Karsant sits down with Corey Bray, author, consultant, and sales enablement leader. Corey takes us through his journey from running prospecting experiments in 2008 to advising hundreds of companies and publishing multiple sales books. He breaks down why many sales teams make things harder than they need to be and how the best reps keep it simple by focusing on clear messaging, a well-defined ICP, and repeatable systems. Corey talks about some mistakes companies make when hiring SDRs without a playbook, the debates that often happen at the leadership level, and the lack of clarity that slows growth. He also shares his view on the rise of AI SDRs, the importance of cutting through today’s noisy market, and why sales enablement should be about building consistency across the team.

How to Stand Out as an SDR – Ep. 10

June 5, 2025

In this episode of Prospecting Pros, hosts John and Chris chat with Arely Brattin, Sales Development Manager at Orum. Arely shares her journey from inbound rep at ZoomInfo to leading Orum's entire sales development program, managing six reps across commercial, enterprise, and strategic accounts. She also reveals three things that make certain SDR candidates stand out from others during hiring. Arely shares how 90% of Orum's meetings come from phone calls, with LinkedIn as a strong secondary channel, while emails prove less effective. She talks about the importance of robust onboarding programs, explaining that even talented hires will fail without the right setup and training. Arely also shares her thoughts on connection rates,data quality, and why former athletes and teachers tend to crush it in sales roles.

The Secrets to Killer Sales Team Development – Ep. 09

May 19, 2025

In this episode of Prospecting Pros, hosts John and Chris chat with Michael Sanchez, a sales training consultant at Growth Genie. Michael shares how he went from door-to-door sales to becoming VP of Sales at Cloud Task, which grew from 25 to over 400 employees during the pandemic as companies pivoted to working remotely. Now at Growth Genie, Michael shares how he's been helping sales teams with over 5 reps improve their conversion rates. He also shares some of the common sales team issues he comes across. Michael talks about how important targeted outreach campaigns are to specific industries and personas rather than generic blasts. He also notes how many established companies even with their polished appearances, still lack basic sales infrastructure. When it comes to team performance, Michael shares the approach he takes to building camaraderie within the team.

How to leverage trending tools for success – Michael Saruggia – Ep. 08

May 14, 2025

In this episode of Prospecting Pros, hosts John and Chris chat with Michael, a go-to-market consultant who specializes in Clay. Michael shares how he pivoted his career after learning a crucial entrepreneurship lesson: "Sell what people want, don't convince them, and sub-niche on something that's already trending." Rather than fighting to create demand, he recommends focusing on converting existing demand. Michael also reveals different use cases for Clay outside of outbound prospecting it has become famous for. He also shares how LinkedIn has been helpful for his own client acquisition, calling it “the new networking” and the exact strategy he uses that creates the impression he’s everywhere in his niche. Michael also shares the alternative approach he’s taking with cold email with its current decline in effectiveness.

Building a Startup with an Engineer’s Approach – Ajinkya Nene – Ep. 07

May 7, 2025

In this episode of Prospecting Pros, hosts John and Chris interview Ajinkya, founder of Trellus, a parallel dialing tool that uniquely embeds within CRMs like HubSpot and Salesforce. Ajinkya gives us a glimpse into his journey from Bay Area engineer to startup founder, describing how he quit his consulting job at 22 without a specific business idea. After a year in "pivot hell," Ajinkya shares the hack that helped him find product-market fit. He also reveals how Trellus was born and how the salesperson's hire acted as the catalyst behind it. Ajinkya also shares what has helped him build a dialer with minimal latency compared to competitors. He observes two emerging sales trends: high-ACV companies focusing on quality outreach with personalization, while low-ACV businesses are increasing volume to hit quotas in a challenging market where "you have to do more to get less these days."

The Key to Finding Message-Market Fit – with Kellen Casebeer – Ep. 06

April 10, 2025

In this episode of Prospecting Pros, hosts John and Patrick interview Kellen Casebeer of The Deal Lab, who shares his journey from high school dropout to fractional VP of sales to founder of his own specialized B2B agency. Kellen's business helps companies find message-market fit by granularly segmenting audiences and testing different messaging approaches. He argues that effective outreach isn't about generic personalization but about demonstrating deep market understanding. Kellen also reveals a clever Clay AI workflow that has helped his clients connect with prospects based on things relevant to their business rather than superficial personalization. On email deliverability, Kellen believes most issues stem from poor targeting rather than technical problems, noting that well-targeted campaigns can run for months without issues.

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