Cai GoGwilt's guest appearances

Cai GoGwilt

Geeks Who Lead Podcast (formerly CTO Connection)

Product Love

IT Visionaries

Pearls On, Gloves Off - Legal Operations, Contracting, Change Management, and Career Growth

Adam Miller

Rachana Kumar

James Kenigsberg

Raghavendra Prabhu

Ryan Graciano

Bob Friday

Kaj van de Loo

Ami Luttwak

Todd Olson

David Schwartz

Paul English

Scott Belsky

Emmanuel Schalit

Jeff Coyle

Eric Anderson

OwlTail

Ironclad

Cai GoGwilt, CTO of Ironclad: core values

For years, technology developers have focused on streamlining best practices for sales and marketing departments across the country, but the same cannot be said about their legal counterparts. After all, no two contracts are the same, right? On this episode of IT Visionaries hosted by producer Hilary Giorgi, Cai GoGwilt, the Co-founder and CTO of  Ironclad talks about how his company is helping legal departments across the country operate more cohesively with their business brethren, why he is an advocate of work-life balance, and why recruiting and training the right people makes all the difference. 3 Key Takeaways  Ironclad is a platform designed to help legal departments automate and speed up their workflow Contracting is more than a legal problem, it’s a collaboration issue Building a team is about finding the right people that fit with the company’s mission  ---  IT Visionaries is brought to you by the Salesforce Customer 360 Platform - the #1 cloud platform for digital transformation of every experience. Build connected experiences, empower every employee, and deliver continuous innovation - with the customer at the center of everything you do. Learn more at salesforce.com/platform

For years, technology developers have focused on streamlining best practices for sales and marketing departments across the country, but the same cannot be said about their legal counterparts. After all, no two contracts are the same, right? On this episode of IT Visionaries hosted by producer Hilary Giorgi, <a href="https://www.linkedin.com/in/cai-gogwilt-77b18a22" rel="nofollow" target="_blank">Cai GoGwilt</a>, the Co-founder and CTO of <a href="https://ironcladapp.com/?&amp;utm_source=google&amp;utm_medium=cpc&amp;utm_campaign=RBL%20%7C%20Search%20%7C%20Brand&amp;_bt=432880375614&amp;_bk=ironclad&amp;_bm=b&amp;_bn=g&amp;_bg=101426813960&amp;gclid=CjwKCAjw_LL2BRAkEiwAv2Y3SWbHEnHbTFiRbGe0y-qFVvnIs7xlcMcfcaYr5oxWA5eR7quirld48RoCTe4QAvD_BwE" rel="nofollow" target="_blank"> Ironclad</a> talks about how his company is helping legal departments across the country operate more cohesively with their business brethren, why he is an advocate of work-life balance, and why recruiting and training the right people makes all the difference. 3 Key Takeaways <ul> <li>Ironclad is a platform designed to help legal departments automate and speed up their workflow</li> <li>Contracting is more than a legal problem, it’s a collaboration issue</li> <li>Building a team is about finding the right people that fit with the company’s mission</li> </ul> --- IT Visionaries is brought to you by the Salesforce Customer 360 Platform - the #1 cloud platform for digital transformation of every experience. Build connected experiences, empower every employee, and deliver continuous innovation - with the customer at the center of everything you do. Learn more at <a href="https://www.salesforce.com/products/platform/overview/" rel="nofollow" target="_blank">salesforce.com/platform</a>

Engineering Change: How Cai GoGwilt and Ironclad are Driving Change in the Legal World

Cai GoGwilt took a fast-tracked, non-traditional road to becoming a CTO at Ironclad. As a non-traditional CTO, Cai sees his role as helping others on the team get unblocked from any issues in their way. This approach has required a bit of humility on Cai’s part as he’s helped cultivate a culture in which engineers have felt comfortable calling him out when he was wrong.On today’s episode of CTO Connection, Peter and Cai discuss Ironclad’s process for annual planning as well as building cross-functional teams in a rapidly scaling company.[00:20] - How Cai became a CTO[01:47] - Leveling up product engineering at Ironclad[06:03] - Core elements of the CTO role[08:54] - Jack of all trades, master of none[12:20] - Creating and sustaining culture[14:12] - Annual planning cycle[18:17] - Hiring a team that cares about the end-user[21:27] - Bringing technology to the law[22:58] - Cross-functional empathy[30:31] - Selecting engineers to thrive in an empathetic culture[34:31] - Finding the right applicants in the Bay areaCTO Connection is where you can learn from the experiences of successful engineering leaders at fast-growth tech startups. Whether you want to learn more about hiring, motivating or managing an engineering team, if you're technical and manage engineers, the CTO Connection podcast is a great resource for learning from your peers!If you'd like to receive new episodes as they're published, please subscribe to CTO Connection in Apple Podcasts, Google Podcasts, Spotify or wherever you get your podcasts. If you enjoyed this episode, please consider leaving a review in Apple Podcasts. It really helps others find the show.Podcast episode production by Dante32.

<a href="https://www.linkedin.com/in/cai-gogwilt-77b18a22/" rel="nofollow" target="_blank">Cai GoGwilt</a> took a fast-tracked, non-traditional road to becoming a CTO at Ironclad. As a non-traditional CTO, Cai sees his role as helping others on the team get unblocked from any issues in their way. This approach has required a bit of humility on Cai’s part as he’s helped cultivate a culture in which engineers have felt comfortable calling him out when he was wrong.On today’s episode of CTO Connection, Peter and Cai discuss Ironclad’s process for annual planning as well as building cross-functional teams in a rapidly scaling company.<ul><li>[00:20] - How Cai became a CTO</li><li>[01:47] - Leveling up product engineering at Ironclad</li><li>[06:03] - Core elements of the CTO role</li><li>[08:54] - Jack of all trades, master of none</li><li>[12:20] - Creating and sustaining culture</li><li>[14:12] - Annual planning cycle</li><li>[18:17] - Hiring a team that cares about the end-user</li><li>[21:27] - Bringing technology to the law</li><li>[22:58] - Cross-functional empathy</li><li>[30:31] - Selecting engineers to thrive in an empathetic culture</li><li>[34:31] - Finding the right applicants in the Bay area</li></ul><a href="https://www.ctoconnection.com" rel="nofollow" target="_blank">CTO Connection</a> is where you can learn from the experiences of successful engineering leaders at fast-growth tech startups. Whether you want to learn more about hiring, motivating or managing an engineering team, if you're technical and manage engineers, the CTO Connection podcast is a great resource for learning from your peers!If you'd like to receive new episodes as they're published, please subscribe to CTO Connection in <a href="https://itunes.apple.com/us/podcast/cto-connection/id1104346760?mt=2" rel="nofollow" target="_blank">Apple Podcasts</a>, <a href="https://podcasts.google.com/?feed=aHR0cHM6Ly9mZWVkcy50cmFuc2lzdG9yLmZtL2N0b2Nvbm5lY3Rpb24%3D" rel="nofollow" target="_blank">Google Podcasts</a>, <a href="https://open.spotify.com/show/3GKpjcEH3ydikWnDDDBpLv?si=vm0dges2QiKoLehoFAR24g" rel="nofollow" target="_blank">Spotify</a> or wherever you get your podcasts. If you enjoyed this episode, please consider leaving a review in <a href="https://itunes.apple.com/us/podcast/cto-connection/id1104346760?mt=2" rel="nofollow" target="_blank">Apple Podcasts</a>. It really helps others find the show.<a href="https://www.dante32.com/" rel="nofollow" target="_blank">Podcast episode production by Dante32.</a>

Cultivating Cross-Functional Teams with Cai GoGwilt