S1 | 18: Facilitating Digital Transformation at The Amenity Collective w/ CIO Dan Cohen

In this conversation we dig into how to create a culture where innovation can thrive from a technology executive who also had a hand in giving our host, Adam Chen, the room to innovate within The Amenity Collective. Listen to the episode to glean advice on how to best let go and build trust in your teams to deliver the outcomes you strive for.

About Dan Cohen

The consummate entrepreneur, Dan has achieved much professional acclaim, including twice operating his companies onto INC Magazine’s 500|5000 list as well as The Daily Record’s 40 Under 40 list. Prior to joining The Amenity Collective, Dan’s track record included his roles as COO / CTO for two technology-focused businesses including a Direct to Consumer eCommerce company, TigerGPS.com, and a Digital Marketing Agency, Mindgrub Technologies. In his current role as CIO of The Amenity Collective, Dan has focused on digitizing the operations of the North American-based Lifestyle and Hospitality services organization. As part of the Digital Transformation, Dan leads a growing team of creative and engineering talent in re-imagining what it means to be a cutting edge services business powered by an integrated digital platform. Dan earned his BSE from Princeton University and his MS in Operations Research from the Georgia Institute of Technology.



In this episode of the Innovation Economy Intrapreneurs Series, we had the pleasure of speaking with Dan Cohen, the CIO and Director of Operations for the Amenity Collective. Dan shared his journey from co-scaling a direct-to-consumer e-commerce business at Tiger GPS to his experience at a digital agency, MindGrab, and how these roles prepared him for the challenges at the Amenity Collective.

Dan defines intrapreneurship as the ability to drive growth and innovation within an existing organization, contrasting it with entrepreneurship, which is about creating something from nothing. He emphasizes the importance of intrapreneurs as internal change agents who form new pathways to facilitate real change within companies.

Throughout our conversation, Dan highlighted the key attributes that distinguish intrapreneurs from entrepreneurs, such as the ability to leverage existing resources and change organizational culture. He shared strategies for gaining buy-in and facilitating change, including understanding organizational goals and presenting unique ways to achieve them.

We delved into the significance of building a culture that fosters innovation, where outcomes are prioritized over tactics, and failure is seen as a learning opportunity. Dan’s leadership style, which I’ve personally benefited from, involves giving team members the space to own their work and the freedom to fail and learn.

Dan also discussed the balance between utilizing existing talent within an organization and identifying skill gaps that require external hires. He stressed the importance of aligning people, processes, and platforms, and the need for executives to budget for time, talent, and treasure to keep these pillars in sync.

Reflecting on his career, Dan shared that one should not fear operating themselves out of a job, as success in one area often leads to new challenges and opportunities for growth. He also touched on the concept of work-life fluidity in today’s remote and hybrid work environments.

For leaders looking to foster an entrepreneurial culture, Dan recommends applying design thinking principles to understand the essence of organizational goals and to think outside the box. This approach can reveal new opportunities and highlight resource gaps that need to be addressed.

In conclusion, our discussion with Dan Cohen provided valuable insights into the world of intrapreneurship and the cultural shifts necessary to support innovation within organizations. His experiences and advice serve as a guide for leaders seeking to harness the entrepreneurial spirit within their teams.

Dan Cohen, CIO, The Amenity Collective