#425 - The AI Playbook for Sales: How to Book More Meetings & Close More Deals With AI | Jake Dunlap

#425 - The AI Playbook for Sales: How to Book More Meetings & Close More Deals With AI | Jake Dunlap

FOUR ACTIONABLE TAKEAWAYS ChatGPT Research Triangle: Before outreach, prompt ChatGPT with the industry (including sub-industry), job title, and your product’s value. This ensures messaging aligns with trends relevant to the prospect. Use Industry Jargon: Ask ChatGPT for insider terminology that VPs in specific industries use. This makes your messaging sound more credible and tailored to their world. Refine Email Sequences: Provide ChatGPT with your email templates and ask it to integrate industry-specific revenue drivers. This keeps messaging structured while adding personalization. Smarter Discovery Questions: Use ChatGPT insights to refine questions that demonstrate expertise. Instead of generic asks, tailor them to industry trends and job-specific challenges. PATH TO PRESIDENT’S CLUB CEO @ Skaled Consulting VP Sales @ Nowait, Inc. (acquired by Yelp) Head of Sales & Customer Success @ Chartbeat Vice President of Sales, Success, and Sales Operations @ Glassdoor RESOURCES DISCUSSED Join our weekly newsletter Things you can steal

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#472 - Why You’re Losing Deals by Not Picking Up the Phone | Michelle Cecil

#472 - Why You’re Losing Deals by Not Picking Up the Phone | Michelle Cecil

Getting your buyer live on the phone isn’t old school—it’s elite. In this episode, Michelle Cecil, two-time President’s Club winner at Procore, shares how dialing instead of emailing builds trust, col...

24 Kesä 202536min

Never Negotiate Over Email (Do This Instead) | Bite-sized Tactics

Never Negotiate Over Email (Do This Instead) | Bite-sized Tactics

Too many reps lose deals by trying to negotiate or explain everything over email. Michelle Cecil (Commercial Sales manager @ Procore) breaks down why you should never negotiate in writing—and what to...

23 Kesä 20258min

#471 - Show The Product on The First Call: The GENIUS High Velocity Sales Blueprint | Mallika Sahay

#471 - Show The Product on The First Call: The GENIUS High Velocity Sales Blueprint | Mallika Sahay

High velocity sales isn’t about rushing… it’s about precision, urgency, and clarity. In this episode, Mallika Sahay breaks down how to build a lightning-fast sales motion without sacrificing quality, ...

19 Kesä 202535min

How to Nail Discovery with a 1-Minute Product Tour (NOT a Demo) | Bite-sized Tactics

How to Nail Discovery with a 1-Minute Product Tour (NOT a Demo) | Bite-sized Tactics

Stop demoing on the first call. Instead, run a 60-second product tour that grabs attention, triggers discovery questions, and opens the door to multi-threading—all before you even show a single slide...

18 Kesä 20255min

#470 - How Top Sales Reps Handle Objections Before They Even Happen | Bryan Charlton

#470 - How Top Sales Reps Handle Objections Before They Even Happen | Bryan Charlton

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 wi...

17 Kesä 202536min

Where Sales Reps Lose Deals Without Even Realizing It | Bite-sized Tactics

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 T...

16 Kesä 20258min

#469 - Everything You’ve Wanted to Learn From a Sales Leader in 30 Minutes | Leadership Q&A

#469 - Everything You’ve Wanted to Learn From a Sales Leader in 30 Minutes | 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 epis...

12 Kesä 202535min

How to Get Hired as an SDR in 2025 (Even Without Experience) | Bite Sized Tactics

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 unconvent...

11 Kesä 20257min

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