March 10, 2026

Why 50% of SDRs Fail When They Become AEs – Ep. 26

In this episode of Prospecting Pros, John sits down with Chris Ritson to talk about the real path from SDR to AE and why that jump is a lot harder than most people think. Chris shares how his own career moved from SDR to AE to sales leadership, and why that experience shaped the way he now coaches reps and SDR leaders. The conversation gets into what actually makes someone successful in an AE role, why so many internal promotions struggle, and why leadership is not always the obvious next step for top SDRs. Chris also talks about ambition, career ownership, and the pressure younger SDR leaders are under in today’s market. It is a thoughtful, honest conversation about sales careers, growth, and figuring out what you actually want, instead of chasing the title that looks best on paper.

Real conversations. Proven strategies. Sales that scale.

Unlock your potential with LevelUp podcast:

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:

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.

Surf and Sales Podcast – The Honest Approach to Cold Calling Success

March 24, 2025

In this value-packed episode of the Surf and Sales Podcast, hosts Scott Leese and Richard Harris dive deep with John Karsant, Founder and CEO of LevelUp Leads (levelupleads.io), on what's actually working in appointment setting and sales development in early 2025. John reveals why the majority of companies have negative experiences with outsourced sales development, and how his approach of radical honesty and setting realistic expectations has led to greater client success. As cold calling continues to drive 80-90% of his agency's results, John shares tactical insights on what's working now, including: Why permission-based openers are becoming less effective and what's replacing them. How tone, pace, and delivery matter more than the actual script content. The role of AI in SDR training, coaching, and call analysis at scale. Why adding a free SDR to struggling accounts helps identify the real problems faster. The conversation takes an unexpected turn when John admits "I'm not a good salesperson, but I'm a terrible liar," revealing how authenticity and a calm, measured approach can be more effective than traditional high-pressure sales tactics. For sales leaders struggling with prospecting effectiveness or considering outsourcing their appointment setting, this episode provides a candid look at what works, what doesn't, and how to evaluate if outsourcing is right for your business. John's unique perspective on entrepreneurship, risk-taking, and building trust in a crowded market offers valuable insights for anyone in sales leadership. Whether you're an SDR, sales manager, or founder handling your own outbound efforts, you'll walk away with actionable strategies to improve your prospecting results and better qualify potential partners. Follow John Karsant on LinkedIn ( / johnkarsant ) or visit levelupleads.io to learn more about his approach to sales development.

LiveChat on your website in the era of AI – with Terry Wilson – Ep. 05

March 5, 2025

In this episode of Prospecting Pros, host John Karsant chats with Terry Wilson, co-founder of Chat Metrics, an Australia-based live chat service. Terry shares how he found out about the power of live chat when his wife's skin clinic saw appointments jump from 2-3 weekly to 3-4 daily after implementing it.

Setting Yourself Apart From Your Competitors – with Devanshu Sinha – Ep. 04

February 26, 2025

On this episode of Prospecting Pros, John Karsant sits down with Devanshu Sinha, a physics PhD dropout who's now making waves with his cold call practice tool called Rehers. Devanshu explains how he stumbled onto his big idea while running Scriptify, when a customer told him their reps got bored with practice bots because "they figured out the trick."

Like what you hear?
Let’s keep leveling up

New episodes weekly with real outbound strategies you can apply today.

Subscribe to our YouTube channel for expert interviews, no-fluff tactics, and behind-the-scenes insights from the world of B2B sales.