Transforming Work with Sophie Wade 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] Global platform partners expand reach to over 100 countries.
[24:31] Top talent understand their worth and if not offered flexibility will work elsewhere.
[25:50] Finding the option(s) that work for each person—where is the middle ground?
[28:08] Research revealed how taxi rides fostered long-term interactions.
[28:46] Engineering connections by mapping users to have facilitated serendipity.
[29:32] Adding personal networks to expand reach, connectivity, and flexible opportunities.
[31:50] Employees can create and plan local events during work trips.
[32:30] Visibility avoids missed connections among nearby remote coworkers.
[33:15] Highlighting common interests to encourage sharing experiences while traveling.
[34:11] In-person sales increase in relevance as AI outreach becomes oversaturated.
[36:02] Commoditized business travel offers few incentives for employees to reduce costs.
[37:15] Incentivizing smart booking combined with uplifts for culture and engagement.
[37:47] Buffers in travel planning processes reveal hidden budget inefficiencies.
[38:55] Roamr is a win-win choice – an optional, flexible alternative to hotels.
[39:18] IMMEDIATE ACTION TIP – How can you think differently about business travel processes to avoid or reduce bloated costs?
RESOURCES
QUOTES
“What if we could make work from anywhere, work from everywhere?”
“It's a platform that helps companies save 30% on their corporate travel accommodation and we do that by paying employees instead of hotels.”
“We believe that’s a way better way to build culture rather than a kind of team building awkward session in the middle of the office.”
“So we’re not just saying we want to save money. We actually want to make the experience better, more intentional, more engaging.”
“How do we find a way to give some flexibility, but also bring teams together and make it work?”
“Everybody can send a million emails now. How are we going to stand out? How we're going to build those relationships?”