Customer Success Career Coach, Career Tips and Proven Job Interview Strategies For Every Customer Success Manager

What if one message could instantly get you into a final round interview?
In this episode, I’m breaking down the real story of how one senior CS leader went from getting rejected in final rounds to landing a Director role in under 60 days. I’ll show you the exact move that got her into a final round interview when she was completely overlooked, and the subtle shift that helped her turn objections into a yes. This is not about working harder, it is about thinking differently.
If you want to stop getting passed over and finally start landing offers, hit play and let’s dive in.
And if you’re done getting so close to offers but still missing out, apply for 1:1 coaching HERE and let’s fix what’s actually holding you back.
00:43 – The one thing that changed everything for Kelly’s job search as a senior CS leader
04:53 – Why strategic outreach matters way more than resume tweaks in landing interviews
06:47 – How a simple outreach message made Kelly the third candidate in a final round, even after the role seemed closed
09:14 – Identifying and crushing objections before they become reasons not to hire you in senior-level interviews
11:26 – The difference between just acknowledging a skill gap and actually showing how you’ll close it for the hiring manager
15:08 – The two learnable skills that turn job searches around
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 [email protected]
HEAD TO THE SHOW NOTES: https://customer-success-career.captivate.fm/episode117
FOLLOW & REVIEW:
Are you loving the podcast? I'd appreciate it if you could take a few seconds to do these two things:
👉🏻 Hit the FOLLOW button so you don't miss out on any new episodes when they drop
👉🏻 And either leave a review on Apple Podcasts or let me know your thoughts by leaving a comment over on Spotify!
This helps me reach more customer success pros who need these insights.
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

What if the only thing standing between you and a higher offer is how you negotiate it?
In this episode, I’m breaking down the 8 negotiation mistakes I see customer success job seekers make that quietly cost them thousands. We’re getting into when to actually negotiate, how to handle that first salary question without boxing yourself in, and the overlooked levers you can pull beyond base salary that most people miss.
If you want to approach your next offer with confidence, use real leverage, and stop leaving money on the table, hit play, because one of these mistakes? You’re probably making it without even realizing.
04:09 – When to negotiate that will give you the most leverage
05:22 – How to answer phone screen salary questions
10:50 – What else you can negotiate besides your salary
16:14 – Why respectful negotiation won’t cost you the offer and exposes red-flag companies
18:31 – Why you shouldn’t skip applying for jobs with low posted salary ranges (even though they are negotiable)
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 [email protected]
HEAD TO THE SHOW NOTES: https://customer-success-career.captivate.fm/episode116
FOLLOW & REVIEW:
Are you loving the podcast? I'd appreciate it if you could take a few seconds to do these two things:
👉🏻 Hit the FOLLOW button so you don't miss out on any new episodes when they drop
👉🏻 And either leave a review on Apple Podcasts or let me know your thoughts by leaving a comment over on Spotify!
This helps me reach more customer success pros who need these insights.
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

What if the reason you’re stuck in your job search… is because you’re not actually searching at all?
In this episode, I’m breaking down why “passively looking” isn’t a strategy (it’s a comfort zone), why handing your resume to a recruiter won’t magically land you opportunities, and the subtle mindset shift that’s keeping you stuck way longer than you need to be. I’ll walk you through what an actual job search looks like and why it’s probably a lot simpler (and more doable) than you think.
By the end, you’ll see exactly where you’ve been spinning your wheels and what to do instead to start creating real momentum. If you want to stop “passively looking” and start landing real opportunities that actually move your career forward, hit play and let’s dive in.
And if you’re ready to stop “passively looking” and start running a job search that actually gets results, apply for coaching HERE and let’s build a strategy that moves you forward.
02:49 – Why Being “Open to Opportunities” Isn’t a Real Strategy
03:42 – Passive Job Searching as a Coping Mechanism (and Why It Keeps You Stuck)
05:47 – The Critical Flaw in Thinking Being Selective Means You Should Be Passive
08:03 – Why Relying on Recruiters Won’t Land You Your Next Role
10:18 – What an Active Job Search Actually Looks Like (And Why It Doesn’t Have to Be Exhausting)
11:28 – How to Be Selective AND Strategic: The Three-Ingredient Formula
14:23 – Why the “Passive” Job Search Is Dead and What to Do Instead
15:36 – What It’s Costing You to Stay Passive in Your Job Search
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 [email protected]
HEAD TO THE SHOW NOTES: https://customer-success-career.captivate.fm/episode115
FOLLOW & REVIEW:
Are you loving the podcast? I'd appreciate it if you could take a few seconds to do these two things:
👉🏻 Hit the FOLLOW button so you don't miss out on any new episodes when they drop
👉🏻 And either leave a review on Apple Podcasts or let me know your thoughts by leaving a comment over on Spotify!
This helps me reach more customer success pros who need these insights.
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

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 [email protected]
HEAD TO THE SHOW NOTES: https://customer-success-career.captivate.fm/episode114
FOLLOW & REVIEW:
Are you loving the podcast? I'd appreciate it if you could take a few seconds to do these two things:
👉🏻 Hit the FOLLOW button so you don't miss out on any new episodes when they drop
👉🏻 And either leave a review on Apple Podcasts or let me know your thoughts by leaving a comment over on Spotify!
This helps me reach more customer success pros who need these insights.
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

Mass applying to jobs might feel productive, but what if it’s actually the exact reason you’re not getting hired? Because after a year of digging into the data, talking to recruiters, and studying how these systems really work, I can tell you, this strategy is doing more harm than you think.
In this episode, I’m breaking down what actually happens when you use mass apply tools and why they can get your resume filtered out before a human even sees it.
I’ll walk you through how this approach makes you look to hiring managers, the hidden ways it’s hurting your positioning, and the long-term career damage most people never even consider. And more importantly, I’ll show you what’s actually working right now, backed by real client data.
If you’re tired of hearing crickets after hitting submit, this will completely reframe your approach. Hit play because the fix might be simpler (and more strategic) than you think.
And if you’re stuck in the apply-and-hear-nothing cycle, apply for coaching HERE and let’s build a strategic job search that actually gets you interviews and results.
00:44 – Why Mass Applying to Jobs Is Sabotaging Your Career (and Not Solving Your Job Search)
02:25 – How Targeted, Quality Applications Lead to Faster Hires and Promotions
06:31 – Why Recruiters Filter Out Mass Applicants (and How to Avoid the “Lazy Candidate” Label)
11:28 – The Cost of Landing the Wrong Job: Why Shortcuts Lead to Short Tenures
18:38 – Are Job Search Services Actually Helping or Just Getting You Flagged?
21:01 – Your Next Job Is the Next Chapter. Here’s How to Make It Count
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 [email protected]
HEAD TO THE SHOW NOTES: https://customer-success-career.captivate.fm/episode113
FOLLOW & REVIEW:
Are you loving the podcast? I'd appreciate it if you could take a few seconds to do these two things:
👉🏻 Hit the FOLLOW button so you don't miss out on any new episodes when they drop
👉🏻 And either leave a review on Apple Podcasts or let me know your thoughts by leaving a comment over on Spotify!
This helps me reach more customer success pros who need these insights.
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