How to Stay Resilient in a Scale-Up | Joe Cripps, CEO of Trail (Series A)

Season #2 Episode #5

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How have you dealt with the ups and downs of Covid-19? Meet Joe Cripps, CEO of Trail, a company that helps multi-site operators in hospitality and leisure to manage their daily tasks.


In this episode, Joe shares his experience of the hospitality crisis, he shares learnings from running a remote-first company, and we talk about the mental health challenges many of us have faced during the pandemic.


Key links:


Trail website:

Joe Cripps profile:

Dave Bailey profile:

Dave's one-on-one guide:


Key timestamps:


[00:56] How did you get the idea for Trail?

[04:10] What was it like when COVID hit?

[08:52] How do you think about the sales process as you come out of COVID?

[11:46] How did you come up with your core messaging?

[14:32] How do you support the team on the emotional side of Covid?

[17:28] What have you learned about remote-first work?

[19:42] How have you integrated business culture in slack?

[21:35] What are the unique challenges for leaders of remote teams?

[22:41] What are the unique challenges for leaders of remote teams?

[24:39] Quickfire Questions


A shout out to co-founder Wil—miss you and let's catch up soon!


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