Ken Weary, COO of Hostaway, on Culture Add in Hiring, Deliberate Decision-Making, and Scaling a Remote Workforce Across 40+ Countries

Supermanagers

Ken’s role as COO at Hostaway, a SaaS startup transforming the vacation rental industry, showcases his innovative approach to remote work and leadership. In discussion with host Aydin Mirzaee, Ken delves into the diverse experiences that have shaped his career, including pivotal positions at Hotjar and his unique journey as a digital nomad. His transition from traditional corporate environments to leading fully remote teams illustrates his commitment to transparency, deliberate decision-making, and culture-driven hiring.

A cornerstone of Ken’s leadership philosophy is fostering an environment where communication and transparency are prioritized. He highlights Hostaway’s structured use of tools like Slack, emphasizing the importance of clear guidelines for synchronous and asynchronous communication. Ken also touches on the significance of building purposeful remote work rituals and the strategic benefits of hiring for culture add rather than culture fit.

In episode 7 of season 2, Ken emphasizes the importance of effective team management through deliberate processes. His insights into remote work dynamics, cultural values, and global team distribution provide listeners with valuable strategies to implement in their own organizations.

Tune in to explore Ken’s techniques and insights that have contributed to Hostaway’s success as a fast-growing, fully remote company with a team located across 40+ countries.

This episode offers a wealth of actionable advice for leaders looking to enhance remote work practices, build strong team cultures, and lead with intention and impact.

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TIME-STAMPED SHOW NOTES:

[03:58] Ken’s journey as a digital nomad

[07:12] Scaling success as former COO of Hotjar

[08:20] Balancing family life and remote work while traveling

[11:17] Remote vs. hybrid, and in-office work

[15:40] Hostaway’s approach to distributed teams and hiring across 40+ countries

[19:57] Synchronous vs. asynchronous communication

[24:30] Why transparency matters in operations

[32:21] Importance of culture add over culture fit

👉 Check out the resources mentioned here: https://fellow.app/supermanagers/ken-weary-hostaway

RESOURCES MENTIONED IN THIS EPISODE:

• Connect with Ken on LinkedIn

• Join the Supermanagers Slack community