How Top Sales Reps Handle Objections Before They Even Happen | Bryan Charlton | Ep. 317
Bryan Charlton joins the show to break down how great reps spot deal risks early and keep momentum all the way to close. He shares real examples, practical tactics, and the mindset his team uses to win complex deals. 🎙 ACTIONABLE TAKEAWAYS: The contract isn’t the finish line. It’s the start. Set the tone for what happens in the first 30, 60, and 90 days so the buyer knows exactly what to expect. If a buyer says they’re looking for a tool, don’t stop there. Dig into the real problems that made them start searching in the first place. Your story has to make sense to everyone. The champion, the leaders, and the end users all need to believe this will actually work. If you’re blocked from talking to power, that’s okay. Just ask what would need to be true for them to feel comfortable making the intro next time. BRYAN’S PATH TO PRESIDENTS CLUB: Spent more than 12 years in sales @ Salesforce and FICO before joining Otter.ai Consistently hit quota by finding high-value deals in unexpected places—selling large software deals to banks in Hawaii, Credit unions, and even AI into tightly regulated financial services firms, while others focused on big brand name accounts RESOURCES DISCUSSED: Bryan’s LinkedIn Join our weekly newsletter Things you can steal Save $50 on any 30MPC course with code “PODCAST” Free Sales Templates, Scripts and Guides
17 Jun 40min
Where Sales Reps Lose Deals Without Even Realizing It | Bite-sized Tactics
Are you losing deals and not even realizing why? Bryan Charleton (Sales Manager @ Otter.ai) shares the two most critical moments in the sales process where deals are either won—or fall apart: 1️⃣ The first discovery call: Learn how elite reps build trust from the first question and become indispensable to buyers. 2️⃣ Stakeholder coverage: Stop going single-threaded. We show you how to cover all the right personas—IT, business leaders, and end users—to close airtight deals. RESOURCES DISCUSSED: Join our weekly newsletter Things you can steal Save $50 on any 30MPC course with code “PODCAST” Free Sales Templates, Scripts and Guides
16 Jun 8min
Everything You’ve Wanted to Learn From a Sales Leader in 30 Minutes | Ep. 316 | Leadership Q&A
Three top sales leaders go deep on the tough stuff: getting promoted, standing out, coaching reps at scale, and whether commission is dead. If you're trying to grow your career or your team, this episode is a goldmine! 🎙 QUESTIONS ANSWERED: How can a sales leader grow fast enough to keep pace with a hyper-growth company? What is the most unconventional or controversial trait to hire for in a sales rep? What part of the sales process should never be automated? How can an SDR stand out among 30+ other applicants? What are three books every modern sales rep and leader should read? How can someone in a leadership role shift out of 90% IC work and into true leadership? RESOURCES DISCUSSED: Cold Calling Sucks (And That’s Why It Works) 30MPC Instagram Join our weekly newsletter Things you can steal Save $50 on any 30MPC course with code “PODCAST”
12 Jun 39min
How to Get Hired as an SDR in 2025 (Even Without Experience) | Bite Sized Tactics
Struggling to land your first SDR job? 3 top sales leaders break down what actually gets you hired for an entry-level sales role in 2025. From cold calling a hiring manager at 5:45am to the unconventional traits that will get you hired, this video is packed with tips that go way beyond generic resume advice. RESOURCES DISCUSSED: Join our weekly newsletter Things you can steal Save $50 on any 30MPC course with code “PODCAST” Free Sales Templates, Scripts and Guides
11 Jun 7min
How to Close Deals FASTER with This SAME DAY Follow-Up Pitch | Anthony Firenzi | Ep. 315
Anthony Firenzi reveals the overlooked power of same-day follow-ups and how this one tactical shift can speed up your sales cycle, build trust, and close deals faster. 🎙 ACTIONABLE TAKEAWAYS: After big team meetings, send a group recap email, personalized 1:1 emails to each attendee, and a quick check-in message to your champion. In executive meetings, come in with a clear agenda, focus on their priorities, and skip small talk to maximize limited time. Compress the time between next steps by scheduling key follow-up calls as early as possible to maintain momentum. Create internal urgency by using internal dynamics or “bad guys” instead of relying solely on external deadlines. ANTHONY’S PATH TO PRESIDENTS CLUB: Revenue Leader @ Unify Corporate AE @ Lattice RESOURCES DISCUSSED: 30MPC Episode 23 Join our weekly newsletter Things you can steal Save $50 on any 30MPC course with code “PODCAST”
10 Jun 38min
Drive Deal Velocity with This Stupid Simple Tactic | Bite Sized Tactics
Struggling with slow deals and stalled follow-ups? Anthony Firenzi (Founding Revenue Leader @ Unify) shares a simple, proven tactic he uses to drive deal velocity: setting same-day next steps. RESOURCES DISCUSSED: Join our weekly newsletter Things you can steal Save $50 on any 30MPC course with code “PODCAST” Free Sales Templates, Scripts and Guides
9 Jun 5min
The “5 Whys” That Will TRANSFORM The Way You Coach Your Sales Reps | Jordan Chavez | Ep. 314
Jordan Chavez shares a proven coaching framework to unlock what motivates your reps, build targeted skill plans, and dig deep with the ‘5 Whys’ to fix what’s really holding them back. 🎙 ACTIONABLE TAKEAWAYS: Use the Five Whys in both discovery and coaching to uncover the real root cause behind problems and drive meaningful change. Ask questions in a way that leads reps on a journey of self-discovery rather than making them feel judged or defensive. Create a quarterly PDP by having reps rate themselves in core areas, then use that to identify gaps, assign KPIs, and set weekly action steps. Role play repeatedly to improve discovery skills, and build trust by going first if the rep isn’t comfortable yet. JORDAN’S PATH TO PRESIDENTS CLUB: Building the Enterprise GTM at Actively.ai 3x Club - IC & Leader @ Navan 8 promotions in 6 years @ Navn RESOURCES DISCUSSED: Join our weekly newsletter Things you can steal Save $50 on any 30MPC course with code “PODCAST” How to Run 1-on-1s Free Sales Templates, Scripts and Guides
5 Jun 39min
The Real Reason Reps Miss Quota | Bite Sized Tactics
Struggling to diagnose why your sales rep isn’t converting? Jordan Chavez (Head of Enterprise GTM @ ActivelyAI) breaks down his “5 Whys” sales coaching framework—a simple, proven method to uncover the real reason behind poor performance. Instead of jumping to surface-level fixes (like “just sell the value”), we’ll show you how to ask layered “why” questions that reveal what’s actually holding your reps back—whether it’s low confidence, weak discovery, or lack of preparation. Whether you're a sales manager, team lead, or AE looking to self-diagnose, this framework will help you stop treating symptoms—and start solving the real problem. RESOURCES DISCUSSED: Join our weekly newsletter Things you can steal Save $50 on any 30MPC course with code “PODCAST” How to Run 1-on-1s Free Sales Templates, Scripts and Guides
4 Jun 7min
