The Customer Success Leadership Podcast

In this episode, we’re tackling one of the toughest questions every CS leader faces: Should you stay… or should you go?

You’ll learn:
 ✔ Why career decisions in CS feel so personal and why leaving can feel harder than it looks
 ✔ The key signs it may be time to move on (growth, impact, values, and energy)
 ✔ The reflection questions to ask yourself before making a big move
 ✔ How to stay with intention or leave with clarity so your next step aligns with your growth

If you’ve been wrestling with this question, this conversation will help you move from rumination to clarity and make a decision you can own with confidence.

Ways I Can Help You Level Up Customer Success:

1. Free CS Leadership Template Library: the templates I use with the CS leaders I coach, from the CS charter to the board report. You’ll also get The Customer Success Leadership Newsletter. Get the templates
2. Lead2Scale: build the strategy and operating model you can defend at the executive table, with me and a small group of CS leaders. Apply at csrevspeak.com/l2s
3. 1:1 coaching: work through a specific challenge, like a reorg, a headcount case or a new role. Book a strategy call
4. Team Enablement:  Two training programs for your CSMs. More details here.
   1. The Strategic CSM builds your team's strategic thinking and business acumen.
   2. The Commercial CSM builds their commercial confidence to drive renewals and expansion.

Let's Connect on Linkedin:  Get weekly insights, templates and real talk on CS leadership. ...

In this episode, we’re breaking down how to position yourself for your next CS leadership role especially in today’s competitive market.

You’ll learn:
✔ How to clarify your unique leadership identity and value
✔ The positioning mistakes most CS leaders make (and how to fix them)
✔ What hiring managers are really looking for beyond the job description
✔ Why visibility, brand, and strategic storytelling make all the difference

Whether you’ve been job searching for months or are just starting to explore what’s next, this episode will help you show up with more clarity, confidence, and direction.

Ways I Can Help You Level Up Customer Success:

1. Free CS Leadership Template Library: the templates I use with the CS leaders I coach, from the CS charter to the board report. You’ll also get The Customer Success Leadership Newsletter. Get the templates
2. Lead2Scale: build the strategy and operating model you can defend at the executive table, with me and a small group of CS leaders. Apply at csrevspeak.com/l2s
3. 1:1 coaching: work through a specific challenge, like a reorg, a headcount case or a new role. Book a strategy call
4. Team Enablement:  Two training programs for your CSMs. More details here.
   1. The Strategic CSM builds your team's strategic thinking and business acumen.
   2. The Commercial CSM builds their commercial confidence to drive renewals and expansion.

Let's Connect on Linkedin:  Get weekly insights, templates and real talk on CS leadership. ...

In this episode, we dive into the mental workload that comes with leading a Customer Success team and how to manage it effectively without burning out.

You’ll learn:
 ✔ How the constant switching between tasks affects your mental clarity and performance
 ✔ The true cost of ignoring mental wellness in leadership
 ✔ Practical strategies for protecting your peace, setting boundaries, and managing your energy
 ✔ How to create a sustainable leadership system that supports your well-being and success

If you’re feeling overwhelmed by the demands of leading a CS team, this episode will help you create the space you need to lead with intention, clarity, and purpose without sacrificing your peace of mind.

Ways I Can Help You Level Up Customer Success:

1. Free CS Leadership Template Library: the templates I use with the CS leaders I coach, from the CS charter to the board report. You’ll also get The Customer Success Leadership Newsletter. Get the templates
2. Lead2Scale: build the strategy and operating model you can defend at the executive table, with me and a small group of CS leaders. Apply at csrevspeak.com/l2s
3. 1:1 coaching: work through a specific challenge, like a reorg, a headcount case or a new role. Book a strategy call
4. Team Enablement:  Two training programs for your CSMs. More details here.
   1. The Strategic CSM builds your team's strategic thinking and business acumen.
   2. The Commercial CSM builds their commercial confidence to drive renewals and expansion.

Let's Connect on Linkedin:  Get weekly insights, templates and real talk on CS leadership. ...

In this episode, we’re tackling one of the toughest challenges Customer Success leaders face: underperformance. When a team member isn’t meeting expectations, it can be hard to pinpoint the root cause. Is it a skill gap? A motivation issue? Or is the system itself setting them up for failure?

You’ll learn:
 ✔ How to diagnose whether the issue is skill, will, or system
 ✔ Why the traditional “skill and will” framework falls short in CS
 ✔ How to evaluate if your team’s underperformance is linked to organizational or process issues
 ✔ How to handle underperformance without jumping to conclusions or making assumptions

Whether you’re facing challenges with your team’s performance or you’re looking for tools to help guide those tough conversations, this episode provides a clear framework to help you lead with clarity, empathy, and intention.

Ways I Can Help You Level Up Customer Success:

1. Free CS Leadership Template Library: the templates I use with the CS leaders I coach, from the CS charter to the board report. You’ll also get The Customer Success Leadership Newsletter. Get the templates
2. Lead2Scale: build the strategy and operating model you can defend at the executive table, with me and a small group of CS leaders. Apply at csrevspeak.com/l2s
3. 1:1 coaching: work through a specific challenge, like a reorg, a headcount case or a new role. Book a strategy call
4. Team Enablement:  Two training programs for your CSMs. More details here.
   1. The Strategic CSM builds your team's strategic thinking and business acumen.
   2. The Commercial CSM builds their commercial confidence to drive renewals and expansion.

Let's Connect on Linkedin:  Get weekly insights, templates and real talk on CS leadership. ...

In this episode, we’re diving into the critical role Customer Success plays in a Product-Led Growth (PLG) motion and how to rethink your CS team’s focus and metrics in a self-serve world.

You’ll learn:
 ✔ What makes PLG fundamentally different from traditional sales-led models
 ✔ How CS can drive value throughout the entire user journey—from sign-up to expansion
 ✔ How to adapt your engagement model and scale success in a product-led environment
 ✔ Key metrics that matter in PLG and how to measure CS impact

Whether you're supporting freemium users, converting trials, or scaling high-touch guidance for power users, this episode will give you clarity on how CS can move the needle in a PLG-driven company.

Ways I Can Help You Level Up Customer Success:

1. Free CS Leadership Template Library: the templates I use with the CS leaders I coach, from the CS charter to the board report. You’ll also get The Customer Success Leadership Newsletter. Get the templates
2. Lead2Scale: build the strategy and operating model you can defend at the executive table, with me and a small group of CS leaders. Apply at csrevspeak.com/l2s
3. 1:1 coaching: work through a specific challenge, like a reorg, a headcount case or a new role. Book a strategy call
4. Team Enablement:  Two training programs for your CSMs. More details here.
   1. The Strategic CSM builds your team's strategic thinking and business acumen.
   2. The Commercial CSM builds their commercial confidence to drive renewals and expansion.

Let's Connect on Linkedin:  Get weekly insights, templates and real talk on CS leadership. ...

In this episode, we’re breaking down how to structure your CSM interview process and find the right fit for your team.

You’ll learn:
 ✔ How to define success and the skills your CSM needs
 ✔ How to design a 4-round interview process for deeper insights
 ✔ Why practical exercises are key to assessing real-world skills
 ✔ How to evaluate cultural fit and alignment with your team

Whether you’re hiring your first CSM or scaling your team, this episode will help you hire with confidence and set your team up for success.

Ways I Can Help You Level Up Customer Success:

1. Free CS Leadership Template Library: the templates I use with the CS leaders I coach, from the CS charter to the board report. You’ll also get The Customer Success Leadership Newsletter. Get the templates
2. Lead2Scale: build the strategy and operating model you can defend at the executive table, with me and a small group of CS leaders. Apply at csrevspeak.com/l2s
3. 1:1 coaching: work through a specific challenge, like a reorg, a headcount case or a new role. Book a strategy call
4. Team Enablement:  Two training programs for your CSMs. More details here.
   1. The Strategic CSM builds your team's strategic thinking and business acumen.
   2. The Commercial CSM builds their commercial confidence to drive renewals and expansion.

Let's Connect on Linkedin:  Get weekly insights, templates and real talk on CS leadership. ...

In this episode, we’re breaking down what actually matters in your first 90 days as a CS leader and how to avoid the chaos that derails so many new leaders.

You’ll learn:
 ✔ Why diagnosing comes before fixing
 ✔ What to focus on in your 30-60-90 day plan
 ✔ How to align with stakeholders and drive early momentum
 ✔ And how to build credibility, clarity, and traction from day one

Whether you're the first CS hire or stepping in to lead an existing team, this episode gives you the structure and strategy to lead with intention.

Ways I Can Help You Level Up Customer Success:

1. Free CS Leadership Template Library: the templates I use with the CS leaders I coach, from the CS charter to the board report. You’ll also get The Customer Success Leadership Newsletter. Get the templates
2. Lead2Scale: build the strategy and operating model you can defend at the executive table, with me and a small group of CS leaders. Apply at csrevspeak.com/l2s
3. 1:1 coaching: work through a specific challenge, like a reorg, a headcount case or a new role. Book a strategy call
4. Team Enablement:  Two training programs for your CSMs. More details here.
   1. The Strategic CSM builds your team's strategic thinking and business acumen.
   2. The Commercial CSM builds their commercial confidence to drive renewals and expansion.

Let's Connect on Linkedin:  Get weekly insights, templates and real talk on CS leadership. ...

In this episode, we’re unpacking the biggest missteps founders make when building out Customer Success and how to avoid them.

You’ll learn:
 ✔ Why hiring one CSM to “figure it out” is a setup for failure
 ✔ What embedding CS into your company culture actually looks like
 ✔ The real reason churn isn’t solved by CS alone
 ✔ And how to measure what actually matters—so you don’t get blindsided later

If you’re a founder building your first CS function or a CS leader working to get buy-in from the top, this episode is for you.

Ways I Can Help You Level Up Customer Success:

1. Free CS Leadership Template Library: the templates I use with the CS leaders I coach, from the CS charter to the board report. You’ll also get The Customer Success Leadership Newsletter. Get the templates
2. Lead2Scale: build the strategy and operating model you can defend at the executive table, with me and a small group of CS leaders. Apply at csrevspeak.com/l2s
3. 1:1 coaching: work through a specific challenge, like a reorg, a headcount case or a new role. Book a strategy call
4. Team Enablement:  Two training programs for your CSMs. More details here.
   1. The Strategic CSM builds your team's strategic thinking and business acumen.
   2. The Commercial CSM builds their commercial confidence to drive renewals and expansion.

Let's Connect on Linkedin:  Get weekly insights, templates and real talk on CS leadership. ...

In this episode, we’re getting honest about what really holds CS teams back from leading effective revenue conversations and what you, as a CS leader, can do to fix it.

You’ll learn:
 ✔ The core mindset shift your CSMs need before anything else
 ✔ Why hesitancy isn’t about discomfort with “selling”; it’s about blind spots
 ✔ How to build situational fluency through coaching and enablement
 ✔ And how to embed revenue enablement into your team’s daily rhythm, tools, and culture

If your team owns renewals or expansions or if you’re rolling out revenue responsibilities soon, this episode is your playbook.

Ways I Can Help You Level Up Customer Success:

1. Free CS Leadership Template Library: the templates I use with the CS leaders I coach, from the CS charter to the board report. You’ll also get The Customer Success Leadership Newsletter. Get the templates
2. Lead2Scale: build the strategy and operating model you can defend at the executive table, with me and a small group of CS leaders. Apply at csrevspeak.com/l2s
3. 1:1 coaching: work through a specific challenge, like a reorg, a headcount case or a new role. Book a strategy call
4. Team Enablement:  Two training programs for your CSMs. More details here.
   1. The Strategic CSM builds your team's strategic thinking and business acumen.
   2. The Commercial CSM builds their commercial confidence to drive renewals and expansion.

Let's Connect on Linkedin:  Get weekly insights, templates and real talk on CS leadership. ...

In this episode, we unpack the leadership blind spots that keep CS leaders stuck and why trying to navigate them alone slows everything down. You’ll learn how coaching can help you build clarity, spot the patterns you’re too close to see, and move forward with sharper focus and confidence. 

This episode explores:
 ✔ Why leadership actually gets harder the more senior you become
 ✔ The difference between experience and awareness (and why both matter)
 ✔ How blind spots show up in your thinking, your org, and your strategy
 ✔ And why coaching can help you accelerate your growth without burning out

If you’re building a CS org, stepping into a bigger role, or feeling stuck somewhere in the middle, this one’s for you. You don’t have to figure it all out alone.

Ways I Can Help You Level Up Customer Success:

1. Free CS Leadership Template Library: the templates I use with the CS leaders I coach, from the CS charter to the board report. You’ll also get The Customer Success Leadership Newsletter. Get the templates
2. Lead2Scale: build the strategy and operating model you can defend at the executive table, with me and a small group of CS leaders. Apply at csrevspeak.com/l2s
3. 1:1 coaching: work through a specific challenge, like a reorg, a headcount case or a new role. Book a strategy call
4. Team Enablement:  Two training programs for your CSMs. More details here.
   1. The Strategic CSM builds your team's strategic thinking and business acumen.
   2. The Commercial CSM builds their commercial confidence to drive renewals and expansion.

Let's Connect on Linkedin:  Get weekly insights, templates and real talk on CS leadership. ...