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Customer Success Career Coach, Career Tips and Proven Job Interview Strategies For Every Customer Success Manager (CSM)
Customer Success Career Coach, Career Tips and Proven Job Interview Strategies For Every Customer Success Manager (CSM)
Customer Success Career Coach is a podcast dedicated to helping current and aspiring Customer Success professionals advance their careers. Hosted by Carly Agar, a 10+ year CS veteran and award-winning career coach, the show offers practical advice, job search strategies, and interview tips. Each episode features actionable insights and real-life stories from industry experts. Topics include career growth hacks, promotion strategies, and navigating the CS job market.
Episodes
142. Overqualified for Some CSM Jobs, Underqualified for Others? How to Decide Which Roles to Apply For
Are you applying for CSM roles feeling either overqualified or underqualified and wondering where you actually fit?In this episode, I’m breaking down how to decide which roles are actually worth your time, why job titles matter way less than you think, and the three things I want you looking at before you apply. I’ll also walk you through when being overqualified is totally fine and how to tell wh
141. 3 CSM Interview Presentation Mistakes That Get You Cut in the Final Round
What if the thing costing you the job in your final round interview presentation is something you don’t even realize you’re doing?I reviewed around 60 coaching calls with Customer Success job seekers preparing for final round presentations and the same three mistakes kept showing up.In this episode, I’m breaking down exactly what they are, how to show the hiring team how you actually think and mak
140. First 90 Days as a CSM: 5 Things That Make Your Manager Think "Good Hire"
Landing the job is one thing. Proving they made the right decision hiring you is another.In this episode, I’m breaking down five things every CSM should do in their first 90 days to make a really good impression and set themselves up for success in the long run. I’m sharing how to figure out what you’re actually measured on, get up to speed faster, build relationships before you need them, use bei
139. 5 Mistakes CSMs Make in the First 5 Minutes of an Interview
That 15 minute recruiter screen you thought was just a casual conversation could be the exact reason you’re not making it to the next round.In this episode, I’m breaking down the five most common mistakes I see CSMs make in those first few minutes and how to avoid them. I’ll show you how to build rapport, structure your background without rambling, make it extremely easy for the recruiter to say y
138. LinkedIn Profile Tips for CSMs: 3 Tweaks That Get You Interviews
You could be the perfect CSM for a role and still never hear from the recruiter simply because your LinkedIn profile isn’t optimized the right way.In this episode, I’m breaking down the three things that need to happen before a recruiter reaches out to you on LinkedIn. I’ll show you how to actually show up in recruiter searches, what makes someone want to click on your profile, and the simple twea
137. How to Prove ROI to Your Customers (4 EASY Steps)
If you can’t put a number on the value you’re creating for your customers, you’re going to struggle to prove why they should keep paying for it.That’s why in this episode, I’m breaking down a simple framework every CSM can use to calculate and present ROI, even if your product feels impossible to measure. I’ll walk you through how to identify where your product is creating financial value, turn th
136. 5 Ways the CSM Role is Changing in 2026 (Beyond the Obvious Stuff)
Everyone’s talking about how the CSM role is changing, but what are companies actually looking for in 2026?I analyzed 25 CSM job descriptions from 2025 and 2026, and there were some really interesting patterns that I don’t hear enough people talking about. I’m breaking down what’s changing around AI, commercial experience, scaled CS and customer value, plus two things I hear CSMs lead with all the
135. You Nailed the CSM Interview and Still Got Rejected. Here's 4 Reasons Why
You can nail every interview question and still lose the CSM job offer to someone else.In this episode, I’m breaking down four reasons that happens, and none of them have to do with your experience or whether your answers were technically good. I’ll show you what hiring managers are actually assessing, how to make your interview stories prove you can replicate your results, why being too humble ca
134. What to (And Not To) Say About AI in Your CS Interviews
If you think telling a hiring manager you use AI to write emails faster is proving your AI fluency, you might be setting the bar way too low.In this episode, I’m breaking down what hiring managers actually want to hear about AI in your CS interviews, why efficiency alone is no longer enough, and four specific ways to show that you’re using AI to make a bigger impact with your customers. I’ll also
133. 3 Quick Resume Edits That Get CSMs More Interviews in 10 Mins or Less
Your resume might be the reason you're not getting interviews and it has nothing to do with your experience.In this episode, I'm sharing three resume edits you can make in 10 minutes or less that help recruiters instantly understand your value. We'll talk about why numbers can actually hurt you without the right context, what hiring managers need to see before they care about your results, and the
132. A CS Hiring Manager Who Interviewed 3,000 CSMs Tells You What Gets You Hired with Michael Boyd
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
131. 3 Reasons You’re Not Landing CS Interviews (And It’s Not Your Experience)
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 looki
130. 5 Things NOT to Say About a Career Gap in a Customer Success Job Interview
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 s
129. 5 Salary Negotiation Mistakes CSMs Make
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
128. How To Impress a CS Hiring Manager (From a CS Hiring Manager) with Eric Clouse
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 e
127. AI Won't Replace You as a CSM (But It Does Raise the Bar) - with Dan Ennis!
AI is not coming for your Customer Success job, but it is changing what great CSMs look like.In this conversation with Dan Ennis, Senior Director of Customer Success at Workato, we unpack what hiring leaders are actually looking for in the age of AI and where most candidates are getting it wrong. You'll hear how AI is raising the bar for interviews, assignments, and day to day customer work, plus
126. 5 CSM Interview Mistakes That Cost You the Offer
The interview mistakes costing you offers are probably not the ones you think they are.In part two of this series, I'm breaking down the final five interview mistakes our coaches see Customer Success candidates make over and over again. I'm sharing why trying to sound polished can actually hurt your performance, the mindset shifts that can help you stop second guessing yourself, and the patterns t
125. 9 Reasons You Freeze in CSM Interviews (And How to Fix Each)
How many times have you walked out of an interview and immediately told yourself, "I'm just bad at interviewing"?In part one of this two part series, I'm breaking down four of the biggest reasons Customer Success candidates freeze, ramble, or go completely blank during interviews. These are real coaching lessons pulled directly from conversations our team has had with hundreds of job seekers. I co
124. How This CSM Got a 40% Interview Conversion Rate (With Special Guest, Mariia!)
Most Customer Success job seekers track their applications. Mariia tracked the data behind her entire job search.In this episode, I'm sitting down with Mariia, a Customer Success Manager who recently landed her dream role in cybersecurity. Because she tracked every part of her job search, we were able to see exactly which activities generated the biggest return on her time and energy and which one
123. 3 Things CS Job Seekers Waste the Most Time On (That Aren’t Getting Them Hired)
What if the reason your job search is not working has nothing to do with your experience and everything to do with the things you keep wasting time on?In this episode, I’m breaking down the three biggest mistakes I see Customer Success job seekers making that feel productive but are actually keeping them stuck longer. I’m sharing the patterns we uncovered from clients who recently landed roles, wh
122. 5 Ways Top Performing CSMs Use Champions to Drive Adoption, Expansion & Renewals in Their Accounts
What if the biggest opportunities in your accounts are being left on the table because you are treating champions like power users instead of strategic partners?In this episode, I’m breaking down the five specific ways top performing CSMs use champions to drive adoption, expansion, and renewals without carrying the entire account on their back.I’m sharing the exact plays I used throughout my CS ca
121. How to Land a Customer Success Job You Actually Love (Not Just Any Job)
The people landing the best Customer Success jobs right now are not the ones applying to hundreds of roles.In this episode, I’m breaking down one of the biggest mistakes I see customer success job seekers making and why it’s actually keeping them stuck longer. I’m sharing the real data behind what’s helping people land interviews right now, why applying to more jobs is not the answer, and the four
120. He Applied to 1,000 CS Jobs and Got 0 Interviews. Here's What Finally Worked
You’re not getting rejected because you are unqualified. You’re getting rejected because you are playing the job search game the same way everyone else is.In this episode, I’m sitting down with Michael, who applied to nearly 1,000 Customer Success jobs without landing a single interview. We unpack the exact shifts that finally changed everything, from the networking strategy that started getting h
119. 4 Steps to Build a Business Case for Your Own Promotion in Customer Success
What if the reason you’re not getting promoted has nothing to do with your performance and everything to do with how you are positioning it?In this episode, I’m walking you through a simple four-step framework to build a business case that actually makes it hard for your company to say no. I dive into how to connect your work to what leadership cares about, how to prove your impact with real numbe
118. 7 Mistakes That Are Making Your CSM Interview Stories Land Flat
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 attenti
117. From Laid Off to Director of CS in 60 Days (the 2 Moves That Made it Happen)
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 i
116. 8 Negotiation Mistakes CS Job Seekers Make (That Cost Them Money)
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 tha
115. The Passive Job Search Is Dead (And Hiring a Recruiter Won't Save You)
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
114. From Senior CSM to People Leader: How to Bridge the Experience Gap
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-th
113. Mass Applying to CS Jobs Is Seriously A Horrible Idea. I’ll Explain Why
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
112. He Spent 2.5 Years Applying to Jobs the Wrong Way. Here's What Finally Worked | Client Spotlight
What if the reason you’re not landing interviews isn’t your experience, but your strategy? In today’s episode, I’m sharing the story of Junior, a Customer Success Manager who applied to over 1,000 jobs across 2.5 years and had almost nothing to show for it except a handful of interviews.In this client spotlight episode, we unpack exactly what changed when he stopped using the “spray and pray” appr
111. The Expansion Playbook for CSMs Who Hate Selling
What if the thing standing between you and your next promotion as a CSM isn’t working harder but learning how to spot expansion opportunities without ever feeling like a salesperson?In this episode, I’m breaking down two ridiculously simple approaches to expansion that you can start using immediately, even on your very next customer call. We’ll walk through the quick “inside-out” method to uncover
110. How to Nail a CSM Interview Presentation (3 Things Companies Are Grading You On)
What if the reason you keep coming in second place in your CSM interviews has nothing to do with your experience and everything to do with what you’re missing in the presentation?In this episode, I’m breaking down the three exact categories hiring teams are grading you on… and yes, I used to be the person creating the scorecards. I’ll show you how to use the prompt like a literal checklist, the ba
109. How to Get Promoted Internally in Customer Success (When a Role Opens on Your Team)
Bold move, but here it is… being a top performer isn’t enough to land you that internal promotion you're eyeing. And if you think your KPIs will carry you to the next level, think again.I get this DM all the time, “Carly, there’s an opening on my team. Should I even bother applying?” In this episode, I’m breaking down exactly what to say the moment a role is posted (yes, I give you the script), wh
108. How to Land a Customer Success Job in Under 90 Days in 2026
If your customer success job search has been dragging on for months, the problem probably isn’t your experience — it’s the strategy you’re using. On today’s episode, I’m pulling back the curtain on exactly how my clients are landing customer success roles in under 90 days, even in a market where most searches take 6–12 months.If you’ve been applying nonstop, tweaking your resume, and still hearing
107. How to Land a $200K Customer Success Job (What 10 High Earners Had in Common)
What if landing a $200K Customer Success role has a lot less to do with your title and a lot more to do with one thing almost no one is tracking?In this episode, I went full data-nerd and analyzed 10 recent clients who all accepted Customer Success offers between $175K–$230K. I pulled apart their resumes, KPIs, career paths, and job search histories to uncover the patterns that actually showed up
106. Treat Your Job Search Like a Customer Success Role (Here's How) with Zach Sanford
What if the reason your job search isn’t working has nothing to do with your experience and everything to do with how you’re showing up? In this episode, I sit back down with Zach Sanford to unpack a powerful shift most Customer Success professionals completely overlook… treating your job search like a CS role.We break down exactly how to demonstrate your CSM skills at every stage of the process—f
105. The Real Reason CSMs Feel Invisible (And Your Action Plan to Fix It) | Part 2
We analyzed 1,474 CSM conversations to uncover why they are leaving and what keeps them in 2026. Grab the Free Talent Report here: https://customer-success-career.captivate.fm/reportCSMs don’t leave because they’re bad at their jobs — they leave because no one can see the impact they’re making. In Part 2 of this series, I’m breaking down the real reason high-performing CSMs feel invisible, even wh
104. 85% of CSM Turnover is Preventable (Here's the Data) | Part 1
We analyzed 1,474 CSM conversations to uncover why they are leaving and what keeps them in 2026. Grab the Talent Report here: https://customer-success-career.captivate.fm/reportWhat if I told you that 85% of CSM turnover is completely preventable — and most leaders are missing the real reason their top performers are walking out the door?In this episode, I break down insights from 1,474 Customer S
103. How to Talk About Career Gaps From Layoffs in Interviews
That line on your resume that makes your stomach drop in interviews isn’t the problem. The way you’re talking about it is. In this episode, I’m breaking down exactly why career gaps and layoffs quietly derail otherwise strong candidates and how most people accidentally confirm an interviewer’s worst fears without realizing it.I walk you through what hiring managers are actually thinking when they
100+ Episodes Later: 3 Career Lessons I Learned From Podcasting
What if the only thing standing between you and your next career breakthrough is a lesson you haven’t learned yet? In this milestone episode, I’m reflecting on 100 plus episodes of podcasting and the unexpected career lessons that came with it. This isn’t a highlight reel or a victory lap. It’s the real mindset shifts that changed how I approach hard things, fear, and consistency in my career and
101. Customer Success Interview Tips: How to Prep for Recruiters vs Hiring Managers
If you have ever walked out of an interview thinking I nailed that and still did not move forward, this episode is your wake up call. Today, I’m breaking down one of the most common reasons qualified CSMs struggle to land offers even when they prepare and practice. Most candidates prep for every interview the exact same way, and it quietly works against them. Recruiters, hiring managers, and cross
100. Customer Success Career Advice: Stop Blindly Following Traditional CS Paths
What if the reason you feel stuck in your Customer Success career has nothing to do with your performance and everything to do with the path you’re blindly following? On today’s episode, I’m unpacking the uncomfortable truth about traditional CS career paths and why doing “the next logical step” can quietly derail your growth, happiness, and earning potential. We’ll talk about why promotions that
99. 3 Ways to Make Your Customer Calls Less Awkward (And Actually Useful)
If your customer calls feel stiff, boring, or like both of you are counting down the minutes until it’s over, you’re not imagining it, and it’s costing you more than you think. That’s why in this episode, I’m breaking down the simple shifts that turn awkward, check-the-box customer calls into conversations your customers actually want to show up to. You’ll learn why leading with the wrong metrics
98. How to Set Up Your Customer Success Job Search for 2026
What if landing your next big career move comes down to one simple shift in how you approach your job search? Most people treat job hunting like a chaotic scramble — hopping between LinkedIn and job boards whenever they feel like it, but never actually gaining momentum. That’s why in this episode, I’m breaking down the exact four time blocks you need to turn your job search from overwhelming to un
97. How One CSM Rebuilt Job Search Momentum After A Tough Rejection (and Landed a $180K Job 8 Weeks Later)
What if the only thing standing between you and a job offer you actually want is a strategy you haven’t heard yet? In this episode, I’m breaking down the real story behind how Amy went from a brutal late-stage rejection at MongoDB to signing a $150K base offer, PLUS negotiating an extra 10K just weeks later.You’ll hear the exact steps she took to rebuild momentum fast, the cold-outreach strategy t
96. Ask Your Family This Question on Thanksgiving (It'll Change Your Life)
What if the fastest way to rebuild your career confidence isn’t another resume update or headline hack, but a game you play at the holiday dinner table? In this quick, punchy episode, I share the deceptively simple activity I first tried with my own family and how it genuinely changed how I see myself and my career.Instead of diving into another round of job searching advice, I break down the powe
95. Two Ways to Use AI to Level Up as a Customer Success Manager
AI isn’t here to replace you—unless you let it. What if you could flip the script and use AI to become the most valuable Customer Success Manager in the room, no matter what your company throws at you (or doesn’t)?In this episode, I reveal the two high-impact ways CSMs are actually leveraging AI to stand out—one that repositions you as a trusted consultant to your customers and another that instan
94. 6 LinkedIn Mistakes Costing You Customer Success Job Interviews
Think your LinkedIn profile is working hard to get you noticed by recruiters? Think again. Most job seekers (yes, even experienced CSMs) are practically invisible and it has nothing to do with the job market, your background, or even your Customer Success resume.In this episode, I break down the six silent LinkedIn mistakes that are killing your visibility and sabotaging your chances of landing th
93. The Resume Makeover That Landed 3 Customer Success Interviews in Under a Month
What if the only thing holding back your Customer Success career is a resume that’s getting ignored even though you KNOW you bring the results, experience, and drive? In this episode, I share the real story of Maya, a seasoned Customer Success Manager (CSM) with a killer track record who was stuck applying into the void. She thought her Customer Success resume was fine... until we tore it apart an
92. How to Make Your Interview Stories Memorable
Have you ever nailed every job interview question but still walked away with nothing but a “thanks, but no thanks”? You’re probably blending in without even realizing it. In this episode, I’m revealing the real reason great Customer Success candidates keep getting passed over. And it’s not your experience, it’s that your stories sound like everyone else’s.That’s why in this episode, I’ll show you
91. Stop Chasing Promotions as a CSM Start Reverse Engineering Them. (Here's How)
Ever feel like your career is stalled because you’re waiting for someone to notice all your hard work? Honestly? That “wait and hope” strategy is costing you months (if not years) on the path to your next promotion.That’s why I’m breaking down the exact step-by-step strategy I use with my coaching clients to reverse engineer their career growth and land promotions in record time. You’ll discover t
90. The 3 Customer Success Interview Tweaks That Helped Sarah Land an AM Role in 3 Weeks
Ever find yourself making it to the final round interview, only to get that dreaded rejection again and again with zero real feedback? I see it all the time, and that’s why in this episode, I’m breaking down exactly why it happens, straight from a real client success story.Meet “Sarah”, ten years deep in Customer Success, landing interviews left and right (we’re talking big-name companies), but so
89. 3 Things To Do This October To Get Ahead In Your Customer Success Job Search
Ever been told to just “wait until after the holidays” before you get serious about your job search? That advice drives me up the wall, and in this episode, I’m breaking down why October is actually the secret launchpad for your next Customer Success job. While everyone else is slowing down, I’ll show you how to get ahead with the same three-part strategy my clients use to land offers while the co
88. The 15-Minute Company Research Method That Lands You the Customer Success Job with Olivia Kot
Think company research has to take hours? Think again. Most job seekers either fall down endless rabbit holes or show up unprepared and it's costing them interviews, offers, and even salary.That’s why in this episode, I bring in Olivia, our Director of Customer Success, to reveal the game-changing strategy for researching any company in just 15 minutes. We’ll show you exactly what to look for (and
87. The Collaboration Skills Every CSM Needs for Promotion
Ever feel like product, sales, or engineering just doesn’t get you, or worse, ignores your most urgent requests? Here’s the uncomfortable truth—being amazing with customers isn’t enough to get you promoted (or even layoff-proof) in Customer Success anymore.In this episode, I share a powerful, never-talked-about strategy that unlocks rapid career growth for CSMs by making you the secret weapon ever
86. From Crickets to Salesforce Offer in 6 Weeks: How a Career Transitioner Landed Her Dream Customer Success Job
What if everything you thought you knew about landing your dream job was wrong? Imagine going from total job-search exhaustion and crickets in your inbox to signing your ideal offer at Salesforce in just six weeks.In this episode, I reveal exactly how my client “Mallory” ditched the grind of endless applications and rejections, and instead used three counterintuitive strategies to break through wi
85. Why You're Sabotaging Your Interviews (And How to Show Up Ready to Win) With Zach Sanford
What if I told you the #1 thing sabotaging your Customer Success interviews isn’t your experience, your skills, or even your nerves... but overthinking before you ever walk in the door? If prepping for interviews sends you spinning into self-doubt and second-guessing every possible question, this episode is the one you can’t afford to skip.I’m sitting down with Zach, our all-star CS coach and tale
84. 91% Success Rate: Why Customer Success Networking with CSMs Won't Get You Hired
Think Customer Success networking is just about DMing recruiters or chatting up random CSMs on LinkedIn? That’s the biggest myth killing your job search right now. Today, I’m sharing the real reason you’re not landing interviews—and it’s not what you think.In this episode, I break down exactly why generic networking is a waste of your energy, and reveal a smarter, data-backed approach that gets yo
83. From Layoff to Offer in 8 Weeks: How Howard Beat the Worst Job Market for CSMs
What if the only thing between you and your next Customer Success role is a smarter job search strategy? In this episode, I sit down with Howard, who went from layoff (with a baby on the way!) to landing his dream job at Zoom in just eight weeks, and in the toughest market we’ve ever seen. He’s sharing the raw truth about what actually works, how to get recruiters to notice you, the difference str
82. Customer Success Interview Scorecards: What Hiring Managers Want to Hear
Think your interview skills are top-notch but still walking away empty-handed? You might be leaving points (and offers) on the table…without even knowing it.In this episode, I’m pulling back the curtain on the real way interviewers score your answers and why vague talk tracks are quietly wrecking your chances. We’ll dive into the truth about the interview scorecard system, run through real-life an
81. How to Track Your Impact as a CSM (Even When Leadership Isn’t)
What if your KPIs are hiding your true impact and that’s why you’re not getting promoted? Most CSMs are tracking what leadership asks and missing the real proof that moves careers forward. If your best work is going unnoticed, you’re not alone. That’s why in this episode, I reveal the three high-impact metrics I personally used to score raise after raise (including how I built a 200k IC role from
80. From Stuck to Hired: 3 Interview Changes This Client Made To Land A Six-Figure Offer
Are you sick of making it to the final interview round, only to watch the offer slip away at the last moment? What if the thing holding you back isn’t your experience, your resume, or even your skills…but just three tiny tweaks to your interview game?In this episode, I break down the exact changes my client made to go from getting ghosted after interviews to locking in two final rounds and a six-f
79. Why “Tell Me About Yourself” Keeps Tripping You Up (And How to Fix It)
Ever nailed your elevator pitch only to get ghosted after the first interview? Here’s the hard truth, “Tell me about yourself” isn’t a trick question, but it’s tripping up even the most seasoned Customer Success pros. In today’s episode, I’m exposing the five most common (yet completely fixable) mistakes that are sabotaging your first impression and keeping your dream CS role just out of reach. Yo
78. I Broke Down 5 Cold Messages That Got CS Job Interviews - Here's What They Had in Common
Sick of pouring your heart into job applications only to get ghosted, again and again? Here’s the truth, cold outreach can actually land you more interviews (double, in fact), but only if you ditch the generic and learn to message like a pro. Most people are doing it all wrong and sabotaging their shot at the job before they even get a reply.Today, I’m tearing the lid off my private vault of cold
77. LinkedIn Myths That Are Costing You Interviews (and What to Do Instead)
Think your LinkedIn is working for you? Think again. If you’re still treating your profile like a digital resume, posting because you think you “should,” or stressing about building a “personal brand” (cringe)—you’re leaving job opportunities on the table.In this episode, I break down the most common LinkedIn myths keeping talented Customer Success job seekers invisible in 2025. Forget everything
76. What CS Hiring Really Looks Like Right Now (For $120K Roles)
Think you need a “perfect” Customer Success resume to land a $120k role? Think again. Two of my clients just scored these coveted jobs. One after a two-year gap, the other coming from, wait for it, a winery. And neither had what most would call a flawless background.In this episode, I break down exactly what got them hired. You’ll hear how they showcased serious revenue impact and built scalable s
75. Customer Success QBRs: Why Customers Ignore Your Meeting Requests (And How to Fix It)
Are your customers ghosting your QBR invites? Let’s be real… every CSM has faced the dreaded silence or worse, the wrong people showing up. But here’s the ugly truth leadership never told you. It’s not your QBR’s timing, your agenda, or your follow-ups. It’s that your meetings are about you, not your customer.In this episode, I break down the single biggest mistake 99% of CSMs make with their QBRs
74. Why You’re Still Stuck in Reactive Mode (And How to Get Out)
What if I told you the secret to being a proactive CSM has nothing to do with having more time?In this episode, I’m walking you through the exact 6-step framework I use with my coaching clients to help them get out of reactive chaos and into strategic, high-impact action—no matter how overwhelming their workload is. You’ll hear how one CSM managing 500+ accounts went from “I don’t even know where
73. Borrow These Sales Tactics to Become a Standout CSM with Sean O’Leary
What if the future of Customer Success looks a lot more like sales, and that's exactly what your career needs? Most CSMs are missing out on huge levers for impact, influence and growth because they’re ignoring proven sales tactics that actually work.In this episode, Sean O’Leary and I rip the lid off conventional CS wisdom and expose the game-changing sales mindsets, sales tactics and habits you’r
72. The $150K Resume: What Sets Apart Top CS Earners
Want to know exactly what it takes to crack $150K+ in Customer Success this year? Spoiler: It’s not a straight climb up the CSM ladder. Most high earners don’t even have the "perfect" resume you’d expect.Inside this episode, I deconstruct the real, actionable strategies from ten clients who recently landed six-figure CS roles. You’ll discover the resume keywords, career moves, and day-to-day behav
71. From Ignored To Interviewed - 4 Real Stories from CS Job Seekers Who Got Results
You’re rewriting your resume, applying nonstop, doing everything right and still getting ghosted. Sound familiar? In this episode, I sit down with four job seekers who were stuck in the same burnout cycle… until one shift flipped everything.They went from overwhelmed and radio silence to inboxes full of interviews, and it wasn’t because they worked harder. We break down the exact outreach, mindset
70. The 3 Critical Job Search Shifts You Need To Make to Land CSM Interviews in 2025
If you’ve been mass applying to jobs, tweaking your resume nonstop and still hearing crickets, this episode is your reality check. Those tactics just aren’t cutting it in 2025. But here’s the good news: I’m breaking down the three strategic pivots that are helping my clients land real interviews at companies they’re actually excited about. Think smarter resumes, LinkedIn profiles that attract (not
69. The CS Job Search Playbook Is Dead: Here's the Evidence
You’ve been told to obsess over resume keywords, send out dozens of applications each week, and reach out to recruiters after every single job posted. But what if I told you those classic job search “secrets” are actually tanking your chances of getting hired in Customer Success?In this episode, I’m diving into the job search advice that’s actively sabotaging your career growth and breaking down w
68. The New Rules of CS Job Hunting: Why Your Experience Isn't Getting You Hired
Are you feeling stuck or frustrated with your job search? You’re not alone, and it’s not your fault. If your CS job hunting experience feels like you're tossing applications into a black hole, this episode is your wake-up call. The truth is, it’s not your lack of experience, a career gap, or missing KPIs that’s keeping you stuck. The job market has done a complete 180 since pre-2020, and the old p
67. Beyond the Check-In: The Questions Top CSMs Use To Build Authority With Customers
If your customer check-ins feel awkward and your QBRs are just you talking at a screen of blank stares, this episode is your tactical reset. I’m sharing the five power questions top CSMs use to turn flat convos into high-impact, expansion-driving moments without needing deep product knowledge or extra prep. These aren’t theoretical frameworks. They’re practical, repeatable questions you can use to
66. I analyzed 11 successful customer success resumes: here’s what they had in common
Ever wonder why your resume keeps getting ghosted, even when your experience checks every box? After combing through 11 before-and-after resumes from job seekers who actually landed CS roles, I uncovered six patterns that turned their apps from invisible to irresistible. And spoiler: it’s not what those cookie-cutter career blogs are telling you.In this episode, I walk you through the exact framew
65. What does a career in CS Ops really look like?
Ever find yourself thinking, “There’s gotta be a better way to do this”? If you’re the CSM who’s constantly rebuilding broken processes in your head, secretly obsessed with structure and scale, and lowkey bored of the same playbooks, this episode is your permission slip to explore CS Ops.In this episode, I’m chatting with Justin, who went from traditional CSM to building CS Ops teams at IBM and tr
64. 4 Ways To Leverage AI And Uplevel Your CSM Game
Being a standout CSM today isn’t about working harder… it’s about working smarter. And if you’re not already using AI to do that, you’re missing a massive opportunity to save time, impress leadership, and build deeper customer relationships.In this episode, I’m sharing four creative ways you can leverage AI that have completely changed the game. From building thought leadership content, to optimiz
63. The Hidden Mechanics of Job Boards: Insider Secrets from Our Expert
Job boards might seem simple. You scroll, you apply, you wait. But behind the scenes? There’s a whole hidden system at play that most job seekers never see. And if you knew how it really worked, you’d job hunt completely differently.In this episode, I’m sitting down with Olivia, our Director of Customer Success and a the go-to hiring insider who’s been behind the curtain at Indeed and Data People.
