What actually separates a great Senior CSM from someone who’s ready to lead a team, and why does that jump feel so much harder than it should?

In this episode, I’m breaking down the real gap no one talks about when stepping into people leadership and why being exceptional at your role isn’t the same as being ready to manage others. I’ll walk you through the mindset shifts, skill gaps, and behind-the-scenes expectations that quietly determine whether you get promoted or passed over.

If you’re ready to stop feeling overlooked and start positioning yourself like a future leader, this will show you what to focus on next. Hit play and let’s dive in.

And if you’re ready to bridge the gap and position yourself as the obvious next leader, apply for coaching HERE and let’s map out your next move together.

01:33 – Why Moving from Senior IC to Leadership Feels Impossible and Why It Isn’t Your Fault

03:16 – Why Waiting For An Internal Promotion Can Keep You Stuck

05:16 – How Targeting Early-Stage Or Founding CSM Roles At Startups Can Be Your Ticket To Player-Coach and Leadership Positions (If You Find The Right Fit)

07:41 – How to Identify Real Player-Coach Opportunities (and Avoid the Trap Roles)

14:37 – The Must-Have Experiences to Compete for Startup CS Leadership Roles

17:19 – How to Position Yourself as the Solution Startups Are Actually Searching For

FREEBIES & RESOURCES:

🛎️ Actively looking for a job in Customer Success or plan to in the near future? Apply for 1:1 Coaching with me HERE

🛎️ Optimize your resume for Customer Success jobs to land consistent interviews with my FREE Training: https://customer-success-career.captivate.fm/resume

🛎️ Learn how to sell yourself as the best candidate & walk into your next Customer Success job interview with confidence with my FREE Training: https://customer-success-career.captivate.fm/sellyourself

🛎️ Learn how to Master Behavioral Interviews with my FREE Training: https://customer-success-career.captivate.fm/behavioral

CONNECT WITH ME:

❤️ Let's be LinkedIn friends: www.linkedin.com/in/carly-agar/

💭 Got any questions? Send me an email at support@carlyagar.com

HEAD TO THE SHOW NOTES: https://customer-success-career.captivate.fm/episode114

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Thanks for tuning in to the Customer Success Career Coach podcast! I'll catch you next week.

New episodes drop every Wednesday!

Mentioned in this episode:

We analyzed 1,474 CSM conversations to uncover why they’re leaving and what actually keeps them in 2026. Grab the free Talent Report here: https://customer-success-career.captivate.fm/report