Customer deals often stall not because the product is weak but because buyers doubt their own ability to make the right choice.

Alex Raymond is joined by Brent Adamson, the co-author of The Challenger Sale, The Challenger Customer, and The Framemaking Sale, and the co-founder of A to B Insight, to discuss why decision confidence drives stronger outcomes than product features or supplier claims. Brent lays out the four forces that undermine confidence inside organizations: decision complexity, information overload, objective misalignment, and outcome uncertainty.

The discussion shows how account managers can step into those moments of doubt and help customers move forward with clarity. What changes when a client ends a conversation not only trusting the solution but feeling more confident in themselves? And how does that shift the way long-term relationships are built? This episode points out a more human approach to account management - one that deepens trust, strengthens renewals, and supports lasting growth.

Episode Breakdown:

00:00 Introduction

03:10 Why Decision Confidence Drives High-Quality, Low-Regret Deals

07:19 Customer Self-Confidence vs Supplier Confidence

16:24 The Four Forces That Undermine Buyer Confidence

18:45 Why Stalled Deals Happen and How to Break Status Quo

27:53 Rep-Free Buying and the Risk Gap for Sales Teams

31:03 The Phrase That Frames and Practical Social Proof

35:59 From Expert to Connector in Account Management

40:35 Humanistic Sales and Helping Customers Trust Themselves

Connect with Brent Adamson:

Website

LinkedIn

Connect with Alex Raymond:

AMplify

LinkedIn

Podcast production and show notes provided by HiveCast.fm

Too many account management teams invest in software before they’re ready, and end up automating the wrong things.

Alex Raymond sits down with Jennifer Pinter, a seasoned expert in account management software, to talk about what separates successful tech stacks from the ones that never gain traction. Jennifer has helped dozens of companies implement tools for AM and CS teams, and she’s seen how often things go sideways when there’s no clear strategy behind the purchase.

Alex and Jennifer discuss the most common missteps, like skipping role clarity, chasing features over outcomes, and underestimating the lift of change management. They also touch on what great teams do differently, from building internal alignment to rolling out new tools in manageable stages.

One key question they keep coming back to: what’s in it for the account manager? If the tool doesn’t make their job easier, adoption won’t stick. And if the team hasn’t nailed the basics like QBRs or account planning, even the best software won’t fix that.

If you’re considering specialized tools for your AM team, or trying to make better use of the ones you already have, this episode will help you rethink how and when software actually supports growth.

Episode Breakdown:

00:00 Why Account Management Needs Its Own Tech Stack

03:56 Start with Role Clarity Before Buying Software

07:07 Why Leadership Buy-In Shapes Adoption

10:54 What AI Failures Teach Us About Tech Strategy

15:03 How Systems Drive Consistency in Account Management

21:41 Using Tech to Improve the Customer Experience

27:08 What’s in It for the Account Manager?

36:26 Are You Ready for Specialized AM Software?

Connect with Jennifer Pinter:

Pavilion

LinkedIn

Connect with Alex Raymond:

AMplify

LinkedIn

Podcast production and show notes provided by HiveCast.fm

Bad forecasts don’t just miss targets. They influence hiring plans, budgets, and boardroom confidence. Former Chief Revenue Officer Cliff Unger joins Alex Raymond to share how account managers can build the accuracy and credibility that drive both company growth and personal career impact.

Drawing from his journey from hardware account management to SaaS leadership, Cliff reveals how forecasting, renewals, and expansions shape business strategy at the highest levels. He explains why “job number one” for revenue leaders is hitting the number, but why accuracy in forecasting is just as critical for winning trust with executives and investors. With only a small fraction of companies forecasting within 5% of actuals, Cliff points out the power of delivering bad news early, balancing realism with ambition, and building systems that eliminate surprises.

Alex and Cliff’s discussion reframes account management as a true commercial growth function, responsible for renewals, expansion, and reliable forecasting, rather than a reactive support role. The insights in this episode show how account managers and CROs alike can move beyond firefighting, strengthen credibility, and become the operators executives rely on to steer strategy and growth.

Episode Breakdown:

00:00 Why Account Managers Shape the Future of a Business

03:13 From Hardware Sales to SaaS Leadership

10:24 The High-Stakes World of SaaS Renewals

13:11 ARR, GRR, and NRR Explained

16:58 Forecasting Under Pressure as a CRO

19:29 Why Forecast Misses Erode Confidence

27:54 The Real Role of a CRO

30:04 Why Account Management Belongs Under the CRO

37:26 Diagnosing Forecast Misses and Reducing Surprises

41:44 Data Integrity and the CRO’s Biggest Pain Point

Connect with Cliff Unger:

LinkedIn

Connect with Alex Raymond:

AMplify Website

LinkedIn

Podcast production and show notes provided by HiveCast.fm