In this episode of Modern Prospecting, host Andre talks with Casey Drake, VP of Sales at Endear. Casey shares how he moved from being the first Account Executive at Endear to leading the sales team. Instead of following the usual SDR/AE model, Casey built a team of full-cycle AEs who manage the entire sales process.
They discuss how the team uses signal-based prospecting and tools like Tiga to improve timing, reduce manual tasks, and focus on real conversations with prospects. Casey explains why the traditional SDR model doesn’t work for their team and how they’ve made changes to improve results.
Topics covered include:
- How Endear approaches outbound sales
- What metrics they track to measure prospecting
- How sales and customer experience work together
- What tools help their team work better
If you’re looking for ways to improve prospecting, update your sales process, or explore new tools, this episode will give you clear steps and ideas to try.
Chapters:00:00 – Introduction
00:13 – From First AE to Sales Leader: Casey’s Startup Journey
05:23 – Redefining Prospecting: Moving Past Traditional Playbooks
07:03 – Learning Sales Without Formal Training
10:15 – Why the SDR/AE Split No Longer Works
15:57 – The Challenge of Scaling in a Niche ICP
19:00 – What’s Blocking Better Sales Engagement
21:09 – How They Target Brands Opening New Stores
25:57 – Using Signals to Spot Revenue Decision-Makers
27:41 – What Signals Matter Most in Prospecting
32:59 – Building Smarter, Not Noisier, Outreach
34:16 – How to Set Up AEs for Better Results
37:47 – Integrating Tiga: Clear Use Cases First
40:10 – Outro
Quotes:"We hand the toughest task in sales—convincing strangers they need something they've never heard of—to the least experienced people on the team. That’s the SDR trap."- Casey Drake
"Nearly everyone says they’re using AI—but most admit they haven’t seen it actually do anything. It’s all hype until it drives real results."- Casey Drake
Featured Guest:Casey Drake
Guest LinkedIn:
https://www.linkedin.com/in/caseybdrake/Guest Website:
http://www.endearhq.com/
