#352 - Challenging Your Reps on Their Deal Risks (Chris Surdi, Ascend)

#352 - Challenging Your Reps on Their Deal Risks (Chris Surdi, Ascend)

FOUR ACTIONABLE TAKEAWAYS Instead of lecturing a rep who hasn't followed expectations, ask what's preventing them from doing the task. This helps identify roadblocks or allows the rep to own up to the issue. When discussing reasons for making a change, focus on three questions: Why do anything? Why with us? Why now? The "why now" should have a specific date tied to an event. Link the urgency of change to concrete events, such as a software switch, new hire, market trends, or growth initiatives like entering a new market. Ask your reps key questions like when the economic buyer last bought something similar and who typically pays for software in their industry to ensure they understand the buyer’s decision-making process. PATH TO PRESIDENT’S CLUB Head of Sales, Retail @ Ascend Strategic Account Manager @ Ascend Strategic Accounts @ Sourcegraph Head of Enterprise Sales @ Segment Enterprise Sales Executive @ Braintree (a PayPal company) RESOURCES DISCUSSED Join our weekly newsletter Things you can steal

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Episoder(610)

#571 - How to Use AI to Identify the Perfect Time to Prospect | Brendan Short

#571 - How to Use AI to Identify the Perfect Time to Prospect | Brendan Short

Most reps use the same signals and get ignored. Brendan Short shows how to find timing signals no one else can see and turn them into outbound that actually gets responses. 🎙️ ACTIONABLE TAKEAWAYS...

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#570 - Cold Email Masterclass: Everything You Need To Book Meetings in 2026

#570 - Cold Email Masterclass: Everything You Need To Book Meetings in 2026

Jason Bay gives a cold email masterclass on what actually gets replies in a market where most reps are ignored. Stop pitching your product and start with a specific company problem that creates urgen...

5 Mai 25min

#569 - How Leaders Can Clarify the Pitch, Stop Paraphrasing, and Actually Add Value | Allison Bouchard ft. Outreach

#569 - How Leaders Can Clarify the Pitch, Stop Paraphrasing, and Actually Add Value | Allison Bouchard ft. Outreach

Get more from Outreach x 30MPC Cut the fluff and win executive buy-in faster by turning complex sales messaging into clear, high-impact ideas your buyer can understand in under three minutes. 🎙...

30 Apr 31min

#568 (Trailer) - Elite Sales Trainer Critiques BRUTAL Cold Call Objection Gauntlets

#568 (Trailer) - Elite Sales Trainer Critiques BRUTAL Cold Call Objection Gauntlets

Full Video Here Jason Bay breaks down 3 real cold calls and shows exactly where reps lose the meeting and how to fix it Stop pitching your product. Start in the buyer’s world with problems they ar...

28 Apr 1min

#567 - How to Turn Cold Outreach Into Real Conversations | Adia Toll

#567 - How to Turn Cold Outreach Into Real Conversations | Adia Toll

In this episode we take how Adia Toll engineered a 72% reply rate by shifting from pitch-first selling to conversation-first prospecting and the exact systems behind it. ACTIONABLE TAKEAWAYS: Gri...

23 Apr 36min

#566 - 3 Brutal Sales Leadership Lessons (Avoid These Mistakes)

#566 - 3 Brutal Sales Leadership Lessons (Avoid These Mistakes)

The sales leadership lessons that changed how Mark Kosoglow leads and scales teams. Mark Kosoglow shares 3 moments that reshaped how he coaches, manages, and hires. Stop creating busywork. Protect r...

21 Apr 12min

#565 - How to Master Social Selling on LinkedIn to Book Meetings | Kade Hinkle

#565 - How to Master Social Selling on LinkedIn to Book Meetings | Kade Hinkle

Kade Hinkle breaks down a repeatable LinkedIn outbound system that turns cold prospects into warm conversations before you ever send the pitch. 🎙️ ACTIONABLE TAKEAWAYS: Use video follow-ups i...

16 Apr 35min

#564 (Trailer) - I Cold Called For 60 Minutes (And Went Slightly Unhinged)

#564 (Trailer) - I Cold Called For 60 Minutes (And Went Slightly Unhinged)

Full video here Alex Murphy cold calls for 60 straight minutes to see how many meetings he can book in real time. No script no safety net just raw dials real objections and live pipeline building....

14 Apr 24s

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