Michael Ley on Agency Networks, Tech Stacks, and the HawkSoft Purple Cow | Connected Conversations in Insurance

In this episode of Connected Conversations in Insurance, Ray Huang sits down with Michael Ley, Director of Network Relations at HawkSoft, to talk about what agency networks and aggregators are doing to stand out and deliver real value beyond commission splits.

Michael shares his journey from a family-owned agency to HawkSoft and breaks down what agencies should look for before joining a network—from book ownership and carrier access to contract terms, transparency, and technology investments.

They also dive into the modern agency tech stack, why the AMS is at the center of it all, and the tools helping agencies work smarter, including CRM, texting and VoIP, e-signatures, and streamlined intake solutions.

Plus, Michael talks about HawkSoft’s customer-first “Purple Cow” philosophy and wraps things up with a fun travel-themed round of “Where Would Michael Sit?”

0:00 Networks Look Alike

00:46 Meet Michael Ley

01:37 What Network Relations Means

03:23 From Teacher to Agent

06:01 Networks vs Associations

06:33 Network Pain Points10:35 Agency Network Checklist

15:27 Tech Stack Talk

17:28 Open APIs and Data Ownership

21:35 Must Have Agency Tools

29:15 Purple Cow Branding

32:35 Culture and User Community

34:10 Travel Game Setup

34:54 Aisle vs Window Debate

35:47 Bathroom Row Stories

36:47 Family Travel Tradeoffs

37:10 Accidental Private Jet

38:02 Subway Seat Strategy

39:42 Rental Shuttle Tactics

41:19 Doctor Waiting Room Picks

41:53 Conference Room Power Seats

43:16 Movie Theater Sweet Spots

44:43 Best Seats in the Stadium

47:39 Airplane Selfie Side Eye

49:28 Season Wrap and Sponsor

Nick Berry on TotalCSR, Microlearning, and Unhinged Insurance Marketing | Connected Conversations in InsuranceIn this episode of Connected Conversations in Insurance, host Ray Huang welcomes former co-host Nick Berry back to the show to share what he’s been up to since leaving Canopy Connect, including his new role as head of marketing at TotalCSR.

Nick explains how TotalCSR helps agencies find, assess, and train talent across personal lines, commercial lines, and health and benefits, including license tracking and a microlearning app designed to reinforce knowledge retention—especially for complex commercial topics.

They discuss common resistance to training, the need for ongoing skills checks, and how staying sharp builds trust as a “trusted advisor.” Ray and Nick then shift to marketing, emphasizing outcome-driven ads, creative that doesn’t look like ads, long-form copy, memes, and delivering value to local audiences rather than relying on direct “get a quote” messaging.00:00 Career With Cool People00:41 Podcast Welcome Back02:27 Nick Joins TotalCSR05:17 What TotalCSR Does07:16 Microlearning For Retention09:34 Canopy Connect Ad Break10:38 Custom Learning Paths13:19 Training Resistance And Trust15:02 Golf Practice Analogy17:23 Insurance Mustache Game20:49 Mayhem Ad Love21:07 Guessing Celebrity Jingle22:29 Progressive and Farmers Faces23:44 Canopy Connect Pitch24:49 Top of Funnel Marketing27:36 Unhinged Ads That Work32:26 Value First Local Ads36:06 Marketing Is Everything38:49 Wrap Up and Where to Find39:53 Final Canopy Connect Outro

Peter Wood on Mentorship, Community, and Collaboration in Insurance | Connected Conversations

Peter Wood didn't find insurance. Insurance found him. In this episode, Carrie sits down with Peter, agency owner at Kraken Insurance Services based in Chandler, Arizona, to talk about what it really takes to build a thriving agency, a strong community, and a mentorship culture that actually works.

Peter shares how Kraken grew from around $5,000 a month in commissions to $350,000 in just 18 months, why he believes your problems are never as unique as you think, and the hard truth he has had to accept about helping people who are not ready to be helped. He also gets into what makes the Winning at Insurance Facebook community different, why listening matters more than talking in this business, and the three pieces of advice he gives every agent whether they are brand new or years into their career.

If you have ever felt like you wanted to help someone more than they wanted to help themselves, or wondered whether the grass is really greener at a higher comp rate, this one is for you.

00:00 Insurance Found Me

00:55 Meet Peter and Kraken

01:30 From Copiers to Captive

03:26 Joining Kraken Growth

06:07 Nationwide Footprint Event

07:25 Collaboration Over Competition

10:06 Peer Learning Communities

11:32 Value Without Expectation

12:51 Fact Finding Sore Thumb

14:20 Coaching With Parma

16:51 Feedback That Stings

18:54 Building Group Culture

20:21 Value Without Expectation

21:40 Mentorship Learning Curve

24:22 Book Recommendations for Leaders

28:35 Listening to Understand

31:31 Canopy Connect Ad Break

32:37 Advice for Agents

33:03 Mentors and Red Flags

36:47 Compensation vs Support

39:58 Closing and Outro