143: Stephen Dooley - Solving for Flexibility: A Creative, Cost-Saving Business Travel Model

Stephen Dooley is Founder of Roamr, a corporate travel accommodation platform built for distributed teams. Merging insights from trust dynamics and the sharing economy, Stephen explains how a personal pain point led to an innovative travel solution rethinking cost structures and workplace needs. He shares how listening to customer feedback evolved the initial concept into a fresh approach to business travel that—being empathetic and practical—supports flexibility, connection, and culture while delivering measurable impact for businesses and employees alike.

 

 

TAKEAWAYS

[01:22] Stephen studies commerce aligning early interests in business and entrepreneurship.

[01:45] A year abroad gives Stephen an exciting experience and global perspective.

[03:11] The year studying in the US sparks Stephen’s ambition and sharpens his interpersonal skills.

[03:47] Graduate research initially focuses on financial technology and wealth management.

[05:15] Stephen is interested in tech-related consumer psychology dynamics and adoption drivers.

[06:25] The sharing economy reverses historical fundamental trust patterns and behaviors.

[07:11] Younger consumers now influence their parents' tech-based adoption decisions.

[08:34] Stephen takes a new role then the pandemic hits, requiring rapid learning.

[09:28] A light bulb moment about new realities for travel, lifestyle and career compatibility.

[09:47] A great workation opportunity is dashed by unaffordable accommodation.

[10:42] Identifying remote work necessities reveal need for better infrastructure.

[11:17] Location flexibility is widespread, but how to take advantage of new opportunities.

[12:21] Societal tailwinds are behind Working From Anywhere and distributed work.

[12:55] Roamr launches with an employee-focused offering home swaps for workations.

[13:49] During customer discovery, many employers ask to apply the model to corporate travel.

[14:20] Employees get alternatives to hotels, financially benefit, and firms save money.

[14:52] Now business travel is more relationship-focused, so culture and collaboration benefits can outweigh reduced costs.

[16:31] Travel expenses can be significant so more than 20% in savings is valuable.

[17:09] Improved culture, engagement, and retention offer meaningful additional benefits.

[19:21] More younger workers understand the Roamr concept and have much interest to connect and network.

[20:09] Hosting income also helps employees towards meaningful financial goals.

[21:04] Roamr aligns CFO cost savings priorities and CPO employee experience goals.

[22:40] G