Reimagining Sales Leadership via a Non-Traditional background to multi billion dollar IPO with Em Daigle

Cracking Outbound

Understanding your buyer changes everything.

In this episode, Todd Busler sits down with Em Daigle, Founder & Chief Automation Officer at OTTO-MATES, to talk about what it really takes to sell to accounting and finance professionals.

Em shares how her background in public accounting shaped her approach to go-to-market strategy, and why trusted relationships are the key to closing deals in this space. She unpacks what most sales teams get wrong about this audience, how to build long-term credibility, and the value of staying close to your customer.

You’ll also hear how product knowledge, curiosity, and patience can transform how teams connect with technical buyers.

In this episode, you’ll learn:

• Why understanding the buyer matters more than urgency
• How to build trust in long, complex sales cycles
• Why education and community are critical for growth

Things to listen for:

(00:00) Introduction

(01:32) Selling to accountants starts with trust

(04:06) Why automation needs a human lens

(07:31) Learning from messaging that flopped

(11:06) Aligning product and sales to win

(15:01) Creative events that actually work

(20:24) How accountants really want to buy

(25:08) Curiosity as a sales superpower

(30:36) Adjusting sales motion for new tech

(34:00) Building trust through peer-led learning