Mastering Outbound Strategy: Tactical tips from founding AE turned CRO in 2.5 years

Cracking Outbound

Isaiah Crossman, former CRO at Tropic, shares his unique journey from account executive to sales leader, discussing how he led his team through explosive growth. He reflects on the importance of finding the right product-market fit and how his approach to outbound sales evolved from his time at Wunderkind to Tropic.

In this episode, Isaiah explains the key role outbound played in his success, the importance of refining sales messaging, and how consistent training and feedback shaped his team’s results. He also dives into the realities of balancing high-volume prospecting with personalized outreach.

In this episode, you’ll learn:

• How to build a high-performing outbound sales team
• The power of consistent training and feedback loops
• Why outbound still works when done right

Things to listen for:

(00:00) Introduction

(03:06) Isaiah’s background and journey to Tropic

(06:12) Joining Tropic as the first sales rep

(07:34) The importance of outbound in building the pipeline

(14:54) Why outbound is still effective in today’s sales environment

(18:38) What differentiates top performers from the rest

(25:56) Why generic outbound messaging fails and how to fix it

(27:37) Swapping jargon for clarity in sales messaging
(29:37) Rethinking disqualification: when pushing leads unlocks hidden value
(32:38) A simple two-question framework for effective discovery
(40:23) Planting differentiators early to beat your top competitor
(43:48) Outpacing larger rivals through service and sales execution