Exploring New Horizons in People Operations: A Conversation with Alex Hilleary - ep. 064

Alex Hilleary, Rick Haney, Kaleem Clarkson
RemotelyOne Episode Image
39 minutes

From Billy Joel to Remote Work! In this lively interview, co-hosts Rick Haney and Kaleem Clarkson welcome Alex Hilleary, co-founder of Gather, later acquired by ChartHop. The conversation begins on a light and fun note as Alex reveals his passion for Billy Joel, and how he has attended Billy's concerts in every city he's lived in.

Our hosts explore Alex's background, delving into his education at Georgetown and participation in the Venture for America program, which eventually led him to Cleveland. They touch on the challenges faced by cities like Cleveland in retaining talent, with a focus on the potential of remote work to address these issues.

In this positive tone, they discuss the impact of COVID-19 on remote work. Alex shares insights into the sudden responsibilities faced by People Operations professionals during the pandemic, navigating the challenges of a swift shift to remote work, internal communications, and the growth of tech companies.

Alex also talks about the creation of the People Ops Community. He explains how it originated as a growth play for Gather, a company born to empower remote work and organically transformed into a space for people operations professionals to connect, share experiences, and seek advice.

Alex delves into the difficulties people ops professionals encountered during the pandemic and their navigation through them, reflecting on the rapid adaptation required, the widespread burnout, and the accelerated growth of tech companies during that period. He emphasizes the newfound responsibilities of people operations in managing internal communications, particularly in smaller and midsize organizations!

Shifting gears, the conversation moves to the main topic for every thought leader in the distributed work realm: remote and hybrid work models. Alex shares his perspective on the ongoing evolution of work structures, emphasizing that many companies, especially smaller ones, are still navigating immediate challenges rather than designing the future of work. He acknowledges the varied pros and cons of different models and stresses the importance of thoughtful design.

A comical anecdote about Alex's experience with long hair during the pandemic, including an awkward moment when he was mistaken for his mother wraps up this engaging installment! You don’t want to miss it.

Thank you for joining us, Alex! From personal interests and experiences to the challenges and transformations within the realm of people operations, remote work, and community building, this one is an insightful and entertaining listen.

Learn more about Alex: