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

Why do you walk out of interviews thinking you nailed your answers… but still don’t get the offer?
In this episode, I’m breaking down the seven mistakes I see candidates make when answering tell me about a time questions and why their stories just aren’t landing the way they think they are. I’ll show you what’s actually going wrong inside your answers, what hiring managers are really paying attention to, and how to fix your stories so they feel clear, structured, and impactful without overthinking every word. These are the exact shifts I teach my clients to help them stand out in a crowded interview process.
You’ll leave knowing how to turn your experience into answers that feel confident and convincing instead of scattered or forgettable. If you want to walk into your next interview knowing exactly how to answer any question with confidence, hit play and let’s dive in.
And if you’re tired of your interview answers falling flat and costing you offers, apply for coaching HERE and let’s turn your stories into answers that actually get you hired.
2:22 – Why leaving out numbers in your interview stories causes interviewers to underestimate your impact
6:21 – How jumping straight into tactics without sharing what’s at stake makes your story less compelling
8:38 – When you spend too much time on context, you risk losing the interviewer before you get to your actions
10:48 – Why giving a general approach instead of a specific example makes it seem like you’re not listening
12:42 – The habit of saying “we” instead of “I” in your stories causes interviewers to question your ownership
14:25 – When your interview answers go over two minutes, you lose attention and risk not being put in front of customers
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/episode118
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 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