What if the best way to hit quota is to stop obsessing over quota?

In this episode of The Emblazers Show, host Tim Riesterer speaks with Carson Heady, Managing Director of Microsoft Elevate, about building a sales organization where winning becomes inevitable. Carson explains why sellers must become indispensable to informed buyers by delivering immediate value, reducing decision risk, and using AI to create relevant outreach without adding to the growing noise.

The conversation also explores Carson’s people-first approach to sales leadership. He shares how managers can uncover what motivates each seller, build probability-driven processes, create pipeline early, and establish daily actions that move deals forward. Finally, Carson explains why leaders should focus less on the pressure of quota and more on the people, partnerships, and repeatable processes they can control.

Tune in to learn:

• How to use AI for personalized outreach that stands out
• Why reducing buyer risk creates stronger sales conversations
• How people and process make sales success inevitable

Episode highlights: 

(00:00) Introduction

(02:24) Meet Carson Heady Managing Director of AI Business Solutions at Microsoft

(04:33) What still works in sales when AI changes the tools around you

(06:14) Why buyers need sellers differently when they already have more data

(08:40) How the bar for relevance has risen in modern sales conversations

(09:45) Helping buyers de-risk decisions instead of pushing them with fear

(12:04) Why a yes, and approach can open more buyer conversations

(13:43) Turning customer objections into more relevant sales outreach

(18:49) Building stronger sales teams around people, process, and purpose

(23:44) How to create a repeatable operating system for sales performance

(26:37) Why early pipeline building creates more options later in the year

(30:00) Creating a culture where teammates, partners, and peers multiply opportunities

(32:14) How to stay focused on people and process when quota pressure hits

(35:24) What sales leaders can do when a quota feels impossible

(37:00) Why focusing on the next right action keeps teams moving forward

Links and Resources:

• Connect with Abby Kerr: https://www.linkedin.com/in/abbycathkerr/
• Connect with Tim Riesterer: https://www.linkedin.com/in/tim-riesterer/ 
• Connect with Carson Heady: https://www.linkedin.com/in/carsonvheady/

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Learn about Carson Heady

Carson V. Heady is a Managing Director at Microsoft, best-selling author, sales leader, and internationally recognized expert in social selling, AI-powered prospecting, and relationship-driven growth. Over more than two decades in sales and leadership, he has built 19 #1 teams across Microsoft, AT&T, Verizon and T-Mobile, generated more than $1 billion in revenue through LinkedIn social selling, and helped organizations turn technology, relationships, and disciplined execution into measurable results. Carson is the author of Moneyball Sales, Salesman on Fire, and Unbeatable, and is a frequent podcast guest and speaker on sales, leadership, resilience, and the future of AI-enabled work.  

Learn about Tim Riesterer

As Chief Strategy Officer at Corporate Visions and Chief Research Officer at Emblaze revenue leaders’ community, Tim Riesterer is a pioneering force in developing customer conversations that break through the status quo and drive measurable business results. His innovative approach helps companies craft differentiated messages and deploy them through powerful self-service and sales-directed tools that consistently outperform traditional content strategies. A recognized expert in value creation and capture, Tim enables organizations to transform their customer conversations through proven methodologies that elevate their market position and drive sustainable growth.

Learn about Abby Kerr 

As Director of Content & Community at Emblaze, Abby Kerr designs content experiences that spark conversations and strengthen the connective tissue between B2B revenue leaders. With a background spanning brand voice strategy, enterprise B2B content, and education, she brings a sharp eye for nuance and a deep understanding of how people learn and grow. A champion of insight-driven storytelling and peer-to-peer learning, Abby helps make Emblaze a place where leaders don’t just consume content—they contribute to it. She’s also a warm, un-shy introvert who reads fiction, asks big questions, and drinks her coffee black.