Caroline Soo, VP of Customer Success APJ at KnowBe4, talks to The Ortus Club about the evolution of the recurring subscription model and her transition from Gartner’s research advisory to leading regional success teams. Caroline argues that a CSM is not a support agent, but a “captain” responsible for navigating a client’s long-term business goals. She emphasises that in an era of Agentic AI and human risk, the most successful leaders are those who seek high-level peer dialogue to refine their “private Wi-Fi,” the deep, authentic relationships that turn transactional roles into strategic partnerships.
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Executive Summary: Key Takeaways
- The Captain’s Mandate: Customer Success is a navigational exercise; if leaders don’t calibrate the “altitude and latitude” of a client’s goals, the partnership will eventually drift.
- Agentic AI in Cybersecurity: The future of human risk management lies in Agentic AI, which uses individual digital footprints to deliver real-time, hyper-personalised training nudges.
- Relator Leadership: Effective leadership often relies on private Wi-Fi, building deep, tribal connections with a team to propel energy into delightful customer experiences.
- The CS vs. Support Myth: Retention is not just a department; it is the sum of every organisational touchpoint, from marketing to the friction-free delivery of board-level reports.
- The 1% Diary: High-performance leadership requires tracking marginal gains and aggressively carving out time for deep work to avoid the “blind leading the blind.”
Caroline Soo’s path to the VP level at KnowBe4 was shaped by a fundamental question: “Does this mission resonate with me?” After years at Gartner, she recognised that leading the APJ Customer Success arm of a maturing SaaS giant required more than just account management. It required a shift in mindset from reactionary sales to strategic partnership. Based in Singapore, Caroline manages the “Kampong” spirit of her team, ensuring that a happy, heard workforce translates into client retention. She believes that in a world of high-pressure metrics, the most important tool at a leader’s disposal is the ability to pause, learn, and recalibrate their direction.
How do you move from reactionary support to strategic navigation?
Caroline explains why she views her role as a captain responsible for the long-term trajectory of her clients.
“We were shifting from a young startup phase, which is sales-focused, to a more mature SaaS evolution. I realised I had the mindset required to help the team transition from being reactionary to becoming strategic partners. This role is about navigating; I see myself as the captain of a ship. If we don’t get the altitude and latitude right, we will end up somewhere we don’t want to be. In a recurring subscription model, you have to move away from just ‘selling things off’ to ensuring the customer is actually reaching their goals through deep adoption.”
Why is Agentic AI the solution to the human risk gap?
Discussing the knowledge-intention-behavior gap, Caroline highlights how AI is making training relevant in real-time.
“The biggest challenge in cybersecurity is the gap between knowing what to do and actually doing it. In the past, an administrator might try to send the same training to everyone, but if a message doesn’t resonate, it’s a missed message. Agentic AI looks at every individual’s unique digital footprint, their phishing results, malware downloads, and training history, and triggers a ‘nudge’ that is relevant to them in real-time. We are moving toward a comprehensive Human Risk Management platform that allows agents to work these complexities out for the client.”
What is the “Private Wi-Fi” of a relator leader?
Reflecting on her CliftonStrengths, Caroline discusses why building a tribe is more effective than broad, public empathy.
“While empathy is like ‘public Wi-Fi’ where you feel for everyone, a Relator has a ‘private Wi-Fi.’ Once I let people in, I build deep, authentic relationships. I view my team as my tribe. This connection propels me to invest my energy into them. I believe a happy, healthy workforce is the only way to deliver truly delightful customer experiences. You have to address the ‘noise,’ fair compensation, and financial success first. Once that foundation is solid, I focus on the ‘Kampong’ spirit, a close-knit village where people look out for one another.”
Why is board-level friction the biggest enemy of retention?
Caroline challenges the misconception that Customer Success is a solo department responsibility.
“The biggest mistake is thinking that Customer Success is just another name for customer support. Retention is the responsibility of the entire organisation. Customer experience involves every single touchpoint. If a client is preparing for a board meeting tomorrow and our report fails them, they will remember that friction for life. Easing that friction and making it easy for the client to portray the product’s value to their own management is the greatest driver for renewals and expansion. You have to ensure the customer is reaching their goals at every interaction.”
How does a 1% Diary help leaders avoid the day-to-day noise?
Caroline shares her obsession with tracking marginal gains to ensure she has time for strategic navigation.
“The question I have been obsessing over is: ‘Where am I spending my time?’ I have started using a ‘1% diary’ to track marginal gains. I realised I often overbooked myself with meetings, leaving no room for deep work. As a leader, if I am not carving out time to navigate the framework, no one else will. If you are lost in the day-to-day ‘noise,’ your signals for the next big decision become unclear. You must calibrate your direction constantly, or it’s just the blind leading the blind. This downtime allows you to switch gears and remain efficient.”
What is the value of daily learning for emotional regulation?
Encouraging an hour of study per day, Caroline explains how downtime prepares CSMs for high-stress client personas.
“Our founder encouraged us to set aside one hour per day for learning. For a CSM who faces many different personas and high-stress situations, this hour is also for emotional regulation. You need that downtime to recharge so that you aren’t distracted by the high-pressure emotions of a client meeting. Taking that pause allows you to gather your thoughts and stay outcome-focused. I conduct monthly skip-level meetings to hear directly from the ground and help my team formulate business cases for their requests. A healthy environment is the prerequisite for performance.”
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Across Caroline’s insights on navigational leadership, the “private Wi-Fi” of tribal teams, and the shift to Agentic AI, one pattern is clear: these challenges aren’t solved in isolation. They require a peer-level perspective and the kind of high-trust dialogue that transcends the daily noise.
Her vision of the “CIO as a Captain” reflects a broader reality: today’s technology and customer success leaders cannot rely on software alone to ensure retention. The most effective executives, especially those managing the human risk of global workforces, actively seek out peer dialogue as a strategic necessity to get the altitude and latitude right.
At The Ortus Club, we host curated executive roundtables that bring together senior leaders facing these exact challenges. Step away from the transactional day-to-day and engage in the kind of open, high-value conversations that help you calibrate your direction for the next big decision.
Frequently Asked Questions
Q: What is the 1% Diary in leadership?
A: It is a time-tracking practice where leaders document small, incremental improvements (marginal gains) in their daily schedule to ensure they are carving out enough time for “deep work” and strategic planning.
Q: How does Agentic AI differ from traditional AI?
A: Traditional AI might generate content based on a prompt. Agentic AI acts more like a personal assistant or agent that can analyse complex data, make decisions, and trigger specific actions (like personalised security nudges) without constant human intervention.
Q: What is the “Knowledge-Intention-Behavior” gap?
A: It is the psychological phenomenon where individuals know a rule (knowledge) and want to follow it (intent), but fail to act on it (behavior). Caroline notes this is a primary focus for modern human risk management.
Q: What does socialising a tool mean in Customer Success?
A: It refers to helping a client integrate new software into their company’s daily habits and culture, ensuring it is adopted by employees rather than just being a sunk cost that is forgotten.
Q: What is the “Kampong Spirit” in a business context?
A: Derived from the Singaporean/Malay term for a village, it refers to a workplace culture of mutual support, where team members look out for one another’s well-being and success.
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