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

When you've interviewed more than 3,000 CSMs, you start to see exactly what separates the candidates who get hired from the ones who don't.
In today's episode, I'm sitting down with Michael Boyd, a three time VP of Customer Success who has hired more than 100 CSMs, to unpack what hiring managers are really looking for in today's market. We talk about how to stand out in technical interviews even if you're not highly technical, the two out of three rule he uses when evaluating candidates, and what AI fluency actually looks like now that it has become an expectation instead of a bonus.
By the end of this conversation, you'll know what hiring managers are actually paying attention to, where candidates often miss the mark, and how to position yourself as the kind of CSM companies want to hire. If you are ready to stop guessing what hiring managers want and start interviewing with more confidence, hit play and let's dive in.
And if you're tired of knowing you're qualified but not getting the offer, apply for coaching HERE and let's help you land your next Customer Success job.
02:30 – What hiring managers actually want before they hire
06:40 – The interview red flags that should make you think twice
11:15 – What technical interviews are really testing
17:15 – The two out of three rule for landing stretch roles
21:20 – Why the best CSMs are becoming more consultative in the age of AI
32:31 – What AI fluency really looks like in an interview
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/episode132
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!

Why are customer success professionals with great experience still getting rejected for interviews?
In this episode, I'm sharing the three biggest shifts happening in today's hiring market that most job seekers are completely missing. I'll explain why experience alone is no longer enough, the common job search strategies that are quietly holding you back, and what hiring managers are actually looking for when they review your resume.
You'll walk away with a completely different perspective on why your applications are being overlooked and what needs to change to start getting interviews again. If you are ready to stop blending in and position yourself as the candidate companies are actually searching for, hit play and let’s dive in.
And if you're ready to stop relying on outdated job search advice, apply for coaching HERE and let's build a strategy that works in today's market.
00:52 – Why having more experience isn't what lands CS interviews anymore
04:03 – The hiring shifts that quietly changed what companies expect from CSMs
07:42 – Why being a great CSM is no longer enough to get hired
10:10 – Why referrals aren't as reliable as they used to be in today's job market
11:09 – The resume mistake that makes you look like every other candidate
14:04 – Why sending more applications could actually be hurting 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 support@carlyagar.com
HEAD TO THE SHOW NOTES: https://customer-success-career.captivate.fm/episode131
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!

What if your career gap is not the problem at all, but the way you're talking about it is?
If you've ever frozen when an interviewer asked about time away from work, this episode will show you exactly how to answer with confidence instead of second guessing yourself.
I'll walk you through the five biggest mistakes I see Customer Success professionals make when explaining a career gap, plus what to say instead so hiring managers focus on your value instead of your time away. You'll walk away with a simple framework to own your story, avoid common interview mistakes, and leave a stronger impression. If you want to stop letting your career gap hold you back, hit play and let’s dive in.
And if you're not sure how to talk about your career gap in interviews, apply for coaching HERE and let's build your answers together.
00:44 – The one interview question that trips up even the most experienced CS professionals
02:39 – Why career gaps are not the problem and what hiring managers actually care about
04:29 – The mistake that makes interviewers question your career gap before you even finish answering
06:20 – Why talking about what you're leaving behind can hurt your chances
07:23 – The overlooked advantage hiding inside your career gap
11:03 – The interview habit that makes you sound less confident without realizing it
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/episode130
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!

Are you making one of the biggest salary negotiation mistakes without even realizing it?
In this episode, I’m breaking down the five negotiation mistakes I see Customer Success Managers make over and over, and why they could be costing you thousands of dollars. I’ll share real coaching stories from my clients, the simple questions that can completely change an offer, and how to negotiate with more confidence without feeling pushy or difficult.
You’ll walk away knowing how to approach your next offer strategically so you can maximize your compensation and avoid leaving money on the table. If you want to get paid what you’re worth and negotiate your next offer with confidence, hit play and let’s dive in.
And if you want expert support from resume to negotiation, apply for coaching HERE and let’s build a job search strategy that gets results.
00:45 – Why one word in your job offer could be costing you thousands
03:39 – The salary negotiation shift most Customer Success Managers never think to make
08:34 – The difference between getting a good offer and getting the best possible one
09:04 – Why playing it safe during salary negotiations can cost you more than you think
11:06 – The negotiation mistake that gives away your leverage before the conversation even starts
14:44 – The biggest salary negotiation mistake Customer Success Managers make after getting an offer
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/episode129
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!

What do Customer Success hiring managers actually notice that most candidates never think about?
In this episode, I'm joined by Customer Success hiring manager Eric Clouse to talk through what actually stands out at every stage of the hiring process. We cover recruiter outreach, resumes, and interviews, along with the mistakes that quietly hurt candidates. We also get into how hiring managers are evaluating AI skills today and what the future of Customer Success means for your career.
You'll walk away with a much clearer understanding of what today's CS leaders are looking for and how to approach your job search more strategically. If you want to stop guessing what hiring managers value and start making stronger career moves, hit play and let's dive in.
And if you're ready to build an outreach strategy that helps you stand out with hiring managers, apply for coaching HERE and let's work together.
01:16 – Why hiring managers think differently than most job seekers realize
04:28 – The LinkedIn outreach mistake that could be costing you interviews
07:13 – What hiring managers actually want to see before they ever read your resume
16:08 – Why tailoring your resume to the job description can backfire
22:06 – The interview mistake that quietly reveals you're not thinking like a CSM
25:54 – What hiring managers are really looking for when they ask about AI
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/episode128
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!