Jason Loomis - "CISOs: Why Culture Eats Strategy for Breakfast?"
Jason Loomis, Chief Information Security Officer at Freshworks, reveals why culture truly eats strategy for breakfast. He delves into the vital role of a supportive, trust-based environment in cybersecurity success. Jason also details how hiring for talent and mindset outperforms checking boxes for technical skills. Leaders can inspire high-performing teams that drive better results by fostering open communication and genuine collaboration.
EPISODE: Jason Loomis Chief Information Security Officer @ Freshworks CISOs: Why Culture Eats Strategy for Breakfast? A Conversation with Jason Loomis 30
Jason Loomis, Chief Information Security Officer at Freshworks, reveals why culture truly eats strategy for breakfast. He delves into the vital role of a supportive, trust-based environment in cybersecurity success. Jason also details how hiring for talent and mindset outperforms checking boxes for technical skills. Leaders can inspire high-performing teams that drive better results by fostering open communication and genuine collaboration. Episode Description
Introduction to Jason Loomis (0:47) Full Podcast Episode (24:57) Episode Highlights (02:34) How Culture Beats Credentials When Looking for Talent (03:22) Defining Culture Through Team’s Decision-Making Process (01:11) Building Trust and Psychological Safety in Cybersecurity Space (02:42) Securing Results Through Collaborative Decision-Making (01:11) How Leadership Cultivates Trust in a Team (2:10) Normalizing Failure to Unlock Team Potential (2:21) Retaining Skills and Talent by Building Authentic Team Culture (2:42) Attracting the Right Team Through Company Culture (2:05) Culture Grows from Top-Down and Bottom-Up (1:25) Celebrating Employee Growth as Your Greatest Achievement (1:00) Win by Emphasizing How Decisions Are Made (0:52) Short - How Culture Beats Credentials When Looking for Talent (00:44) Short - How Leadership Cultivates Trust in a Team (00:40) Table of Contents
(00:47) Introduction to Jason Loomis “We focus on three things in cyber: people, process, and technology. If you don’t have the people, the process and technology go right out the door. So, it starts with people first. I'm a people-first CISO.”
Full Episode "The biggest failure I see in leadership is focusing solely on finding someone with specific skills, assuming that’s the key to success. To me, nothing could be further from the truth. You should start by asking how they will fit into the culture we’re building. If they have a people-first mindset, with process and technology coming second, that’s what I look for."
(02:34) Episode Highlights
(03:22) How Culture Beats Credentials When Looking for Talent “I hire for fit. Do they fit the team? Do they align with the culture I'm building? If so, everything else is ancillary.”
(01:11) Defining Culture Through Team’s Decision-Making Process “How do I define my culture? I think I've summed it up in one sentence: how my teams make decisions is more important than the decisions themselves. That’s the theme I go by—focusing on how we approach the team decision-making process.”
(02:42) Building Trust and Psychological Safety in Cybersecurity Space “At the foundation of every high-functioning team is trust, which comes from showing vulnerability and fostering psychological safety. You have to build it. I believe it's the leader's responsibility, but the team can also help foster it.”
(01:11) Securing Results Through Collaborative Decision-Making “You need to have good cognitive conflict, meaning not affective conflict. Affective conflict occurs when you disagree with the person, whereas cognitive conflict focuses on the idea or argument. Good cognitive conflict requires trust within the team to facilitate productive discussions and make better decisions.”
(02:10) How Leadership Cultivates Trust in a Team “It takes time, practice, and effort—repeated over a long period—to be successful in leadership. One way to achieve this is by being vulnerable with your team, and a key part of that is admitting failures. You build trust by removing the fear of failure and normalizing it. It's okay if we fail; what matters is how we pick ourselves back up and learn from it.”
(02:21) Normalizing Failure to Unlock Team Potential “The goals are to be successful, hit our targets, and meet our deadlines, but we also understand that failures will happen along the way. That’s a normal part of the process.”
(02:42) Retaining Skills and Talent by Building Authentic Team Culture “I believe in the statement that people don’t leave companies; they leave their managers. It’s ultimately up to the manager to drive retention. The way to do that is by building a great culture—one where people want to come to work and enjoy being part of the team.”
(02:05) Attracting the Right Team Through Company Culture “During the deeper interviews, that's when you discover cultural fit. You start discussing things like leadership style and the key influences in a person's life. Especially when they ask me about the culture and the team—that’s when I dive into what I'm trying to build here and what I'm looking for.”
(01:25) Culture Grows from Top-Down and Bottom-Up “Be the CEO of your department—determine the culture you want, work with your team to build it, and don’t let anyone tell you otherwise.”
(01:00) Celebrating Employee Growth as Your Greatest Achievement “I'm honestly most proud when people leave me and move on to better roles. Seeing them grow, become their best selves, and knowing I contributed to their career—that's what makes me proud.”
(00:52) Win by Emphasizing How Decisions Are Made “Think about how you're approaching this decision as a group. Do I involve the team? Am I getting buy-in? Do I have their trust? Is there the right amount of healthy conflict to make the best decisions? All of this leads not only to good decision-making but also to a high-functioning team.”
YOUTUBE SHORT: “I hire for fit. Do they fit the team? Do they align with the culture I'm building? If so, everything else is ancillary.” - Jason Loomis
YOUTUBE SHORT: “It takes time, practice, and effort—repeated over a long period—to be successful in leadership. One way to achieve this is by being vulnerable with your team, and a key part of that is admitting failures. You build trust by removing the fear of failure and normalizing it. It's okay if we fail; what matters is how we pick ourselves back up and learn from it.” - Jason Loomis
Jason Loomis Jason Loomis, Chief Information Security Officer at Freshworks, reveals why culture truly eats strategy for breakfast. He delves into the vital role of a supportive, trust-based environment in cybersecurity success. Jason also details how hiring for talent and mindset outperforms checking boxes for technical skills. Leaders can inspire high-performing teams that drive better results by fostering open communication and genuine collaboration.
About Eastridge Established in 1972, Eastridge Workforce Solutions is an employee-owned provider of full-service talent acquisition and management solutions for companies globally. Eastridge provides a full range of solutions including professional / technical and industrial staffing. We also provide workforce management solutions such as employer of record, recruitment process outsourcing, as well as managed service provider programs. Our services are backed with Talient, a proprietary workforce technology that streamlines every step of managing your extended workforce.
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