Episode Player

From 100 Workflows to 12: A CRM Reset with Bryan Ossa

ON THE MOVE: Transportation Sales & Marketing Success Stories

Chapters
0:00
Welcome To On The Move
1:07
Brian’s Path Into CRM Architecture
4:15
Why Systems Must Align Teams
5:20
The Problem With RevOps Thinking
6:26
Customer Success As A Sales Driver
9:00
TMSA Elevate Showcase Preview
10:10
Freight Brokerage Intake Form Overhaul
13:05
Workflow Bloat And AI Shortcuts
19:15
Documentation That Stays Current
21:24
Maximize The Minimal Workflow Design
24:48
What Changed After Simplification
27:09
Cutting Notification Noise And Misses
27:44
Personal Inbox Filtering Quick Win
28:57
What Attendees Will See Onstage
30:53
Advice To A Younger Self
35:22
Closing And Denver Invitation
ON THE MOVE: Transportation Sales & Marketing Success Stories
From 100 Workflows to 12: A CRM Reset with Bryan Ossa
Apr 01, 2026
Jennifer Karpus-Romain

Jen sits down with Bryan Ossa, Co-Founder and COO of Cartographer Consulting, and one of the four finalists selected for the AI & Tech Showdown opening keynote at TMSA ELEVATE.

Bryan shares the story behind a CRM transformation for a transportation brokerage managing more than 1,000 shipments per month. Faced with notification overload, duplicate records, and conflicting automation, the company was struggling to keep track of customer requests and was close to abandoning its CRM altogether.

In this episode, Jen and Bryan explore the operational realities behind CRM success, why over-engineering automation can create more problems than it solves, and what it takes to turn a system teams avoid into one they actually rely on.

Check out the Transportation Sales and Marketing Association (TMSA) website or engage with us on LinkedIn.