Customer Success Career Coach, Career Tips and Proven Job Interview Strategies For Every Customer Success Manager · 2026-07-29 · 24 min
Key moments - from our scoring
Substance score
30 / 100
Five dimensions, 20 points each
The job market for customer success roles has fundamentally changed, and most candidates are competing using outdated strategies. Carly Agar outlines three structural shifts: first, hiring scrutiny means every CS headcount must now justify a specific outcome rather than simply filling a seat; second, AI is automating routine tasks like QBRs, reporting, and email drafts, leaving only high-judgment work like advisory, consulting, and change management; third, customer expectations have compressed timelines - companies want measurable outcomes in 14 days, not 90. Together, these forces mean hiring managers no longer evaluate whether you're "a good CSM" but whether you're "the specific CSM for our specific problem." This makes three common approaches counterproductive: relying on referrals (statistically unlikely when needs are hyper-specific), tweaking resumes to match job descriptions (which homogenizes you with thousands of others doing the same thing and doesn't capture what hiring managers actually want), and mass applying via reverse recruiters or auto-tools (yielding 1% interview rates versus 8-50% for targeted approaches). The solution isn't visibility - it's specificity. Candidates must identify and articulate the unique combination of skills that differentiates them from other CSMs, then position themselves as the solution to a particular company's problem rather than a generic feature-list.
The market has shifted from hiring CSMs to fill seats to hiring specific profiles who solve specific problems. You're likely using a volume strategy (mass applying, keyword-matching your resume) when the market now demands specificity - hiring managers want to know if you solve their unique challenge, not whether you're generally qualified.
No - it actually hurts you. Keyword-matching makes you look identical to thousands of other candidates doing the same thing, and job descriptions don't capture what hiring managers truly want anyway (they often omit key priorities due to laziness in reusing old postings).
Three factors: tech spending scrutiny means every headcount must justify a specific outcome; AI is automating routine work like QBRs and reporting, leaving only high-judgment advisory and consulting; and customer expectations demand results in 14 days, not 90, forcing companies to hire people who can immediately contribute.
Referrals alone are risky because they require someone in your network to know someone at a hiring company whose specific needs match you right now - odds drop dramatically as roles become more narrowly defined. Use referrals alongside a targeted strategy, not as your sole approach.
Reflect on the specific combination of skills you bring that other CSMs don't - not generic traits like 'building relationships' or 'customer obsession,' but concrete differentiators. If you can't answer this, you have a specificity problem that's causing your resume to be overlooked.
Our reviewer’s read on each dimension, with quotes from the episode.
The episode contains a few genuinely non-obvious observations - AI hollowing out commodity CS work leaving only judgment-based tasks, and the shift from 'fill a seat' to 'solve a specific problem' hiring logic - but these ideas are not developed deeply. A significant portion of the runtime is devoted to promoting a masterclass, and the episode deliberately withholds its promised 3-step framework, reducing the net insight delivered.
AI is eating away the commodity work of customer success... What's left in the role is the hard stuff. It's judgment. It's creative problem solving. It's being an advisor, being a consultant, change management, the stuff that AI cannot do.
companies are no longer hiring for the job that you've been doing for the last 12 years. They are hiring for this new phase of CS.
The critique of keyword-matching resumes as counterproductive (making you look generic rather than specific) and the volume-vs-specificity reframe are moderately contrarian takes for a CS career audience. However, the underlying ideas are repackaged from mainstream marketing and career-coaching circles, and the 'you can't read the label from inside the jar' line is a well-worn phrase that underscores the recycled thinking.
By the time you've made yourself feel fit this job description, you are now just a generic CSM. And guess what? Your resume looks exactly like the 5000 other CSMs who also are doing the same keyword matching.
you can't read the label from inside the jar
This is a solo monologue by the host, a CS career coach. There is no guest to evaluate. Carly Agar is relevant to the niche and references working with 1,200+ CS professionals, but she is a career coach rather than a senior CS practitioner or operator who has built or led CS teams at scale, which limits the depth of practitioner credibility on offer.
I'm Carly Agar, Customer Success veteran, award winning career coach and your go to for getting hired and promoted in Customer Success.
I've now watched well over 1200 customer success professionals hit this exact wall.
The clearest data point - 1% interview conversion for mass-applying tools versus 8% or higher for targeted approaches - is concrete and directionally useful, though the sourcing is vague ('the software companies who power these reverse recruiters'). The composite job-spec example is helpfully detailed. No named companies, clients, or verifiable external sources appear, keeping the ceiling low.
the people who use our platforms convert at 1%, one interview per 100 applications. Our clients who are not mass applying right now get at least an 8% interview rate, some up to 50, 60%.
we're looking for a CSM who has about five years of experience, can talk to executives at uh, complex enterprise companies, can handle themselves in a technical conversation with an engineer, can run a renewal or upsell sales process on their own
This is a solo monologue with no guest, no interviewer questions, and no dialogue to evaluate. The host anticipates objections in a scripted way and demonstrates some rhetorical self-awareness, but the episode functions primarily as a lead-generation funnel for a paid masterclass, with the substantive framework explicitly withheld to drive sign-ups.
I'm not going to try to cram it into, uh, the last two minutes of a podcast episode.
Go grab your seat right now. There's no reason to wait.
Computed from the transcript - who did the talking, and the words that came up most.
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.
Transcribed and scored by The B2B Podcast Index.
Speaker A: What if the only thing standing between you and your next big career milestone is just a strategy you haven't heard yet? I'm Carly Agar, Customer Success veteran, award winning career coach and your go to for getting hired and promoted in Customer Success. Whether you're breaking into the field or ready to level up into leadership, this podcast is your shortcut to real career growth. Every episode is packed with practical takeaways, data backed strategies and zero fluff advice that actually works so you can start making moves towards your goals immediately. If you're ready to take control of your career, well then you're in the right place. Welcome to the Customer Success Career Coach Podcast. The CSM who just got the interview that you got rejected from probably doesn't even have more experience than you. I can say this with confidence because I have seen both resumes hundreds of times now. That person that got the interview, they're not necessarily smarter than you, they don't necessarily have better numbers than you, they have not necessarily been a CSM longer than you. They, uh, just understood something about this market that you don't yet understand. And by the end of this episode, you will understand. Welcome back to the Customer Success Career Coach Podcast. I'm Carly. Before we start, I just want to shout out that tomorrow I'm running a free live masterclass. If you've never been to one of my masterclasses before, they get rave reviews. I am all about no fluff, no bs. Like you're going to get in there, you're going to learn a lot. You're going to leave there thinking how on earth was this free? So you should absolutely come. The masterclass is how to land interviews for competitive customer success jobs. So whether you're in the thick of a job search right now or plan to be in the near future, you should absolutely join me live. I'm going to show you exactly what not to do to land interviews, save you a lot of time and frustration. And I'll show you exactly what to do to land competitive interviews in order to save your spot. Just go to carlyagar.com landinterviews that link is also in the show notes. Go grab your seat right now. There's no reason to wait. Back to what I was saying earlier. That CSM that got the interview that you got rejected from is not necessarily a better CSM than you. What I've noticed is you've been told that the market is bad because there's more talent in it, there's more CSMs, fewer roles, everybody's competing with everybody. And that is absolutely true. There are definitely more people in the job market than there ever have been and that just continues to, to grow. But what I need you to notice is that doesn't actually explain your problem. Because if this was purely a volume game, just a big pile of people fighting over fewer jobs, then the most qualified people would still be getting through. That's how volume works, right? Like the more competition there is, the quote unquote, better competition gets through and the folks with less experience don't get through and they have to wait until it's their turn. But that's not what's happening. I'm seeing so many CS professionals with incredible resumes, great metrics, years of experience, niche skills, and they're just getting ignored. So if you're qualified, you've clearly done the job, you've got the years, the logos, the numbers, and you're still not getting interviews. Volume isn't the whole story. There's something else that's going on and that's really why you're stuck. So I'm going to explain exactly what is going on. Number one, spend in the tech industry has been under a microscope, especially in the last few years. I'm not going to go through all the history. We all know this tech has been suffering for the last few years. So what happens is a job wreck that got posted used to just be like, oh yeah, we have a ton of accounts, we need another csm, we need a new body in a seat. Done, approved, great, go hire someone that's not getting approved anymore. You can't just say we have a lot of accounts, we need another csm. Every team is expected to do more with less. So now every job wreck, uh, that even gets brought up is heavily scrutinized. Every headcount has to be justified against a specific outcome. This profile doing this specific thing with this specific skill set is going to return this specific number. And that changes everything about job seeking. Because the specific profile, solving the specific problem is who they're looking for. They're no longer just looking for a CSM to fill a seat. Number two, AI obviously has made a huge impact in our world over the last couple of years, specifically the last year. AI is eating away the commodity work of customer success. So think about all the parts of your job that are getting automated. Making QBR decks check in calls, usage, reporting, support tickets, the first draft of an email. All that stuff was easy stuff, but it was time consuming. So what's left in the role is the hard stuff. It's judgment. It's creative problem solving. It's being an advisor, being a consultant, change management, the stuff that AI cannot do. Which means, and I need you to really hear this, companies are no longer hiring for the job that you've been doing for the last 12 years. They are hiring for this new phase of CS. They're hiring for what's left after AI completely takes over all the easy shit. So they're not even hiring for the same job. And number three, what's also happening is customer expectations are higher than ever. In this world of AI, I'm sure you know, you all know this even better than me, but in the world of AI, they're so. The expectations are outrageous. They need outcomes faster than ever. There's no longer a, uh, oh yeah, let's check in in 90 days and see if you've achieved your first desired outcome. No, it's like I want to see my first outcome in 14 days and if I don't see that outcome, then I'm going to go find a solution elsewhere because there are so many other solutions. So the person who gets the job, the job that you're competing for, the CSM role, wherever it is, you have to be immediately useful to your team. You can't be someone who only checks a couple of boxes. You need to check all their boxes so you can jump in there and start making an impact with customers pretty quickly. So more pressure on the from the customer means more pressure on the team means they have to hire the perfect fit for their company, their product, their customers, all of the things. So to summarize, all of these kind of like macroeconomic things going on, there's fewer CS jobs out there, there's more talent. Each of these jobs has gotten defined more narrowly. Each of these jobs is demanding more. It's more specific. We're not just looking for an enterprise CSM with five years of experience. We're looking for a CSM who has about five years of experience, can talk to executives at uh, complex enterprise companies, can handle themselves in a technical conversation with an engineer, can run a renewal or upsell sales process on their own, by the way, they can also handle the negotiation. And maybe this person's going to come in and teach our team a thing or two about AI. It's gotten extremely specific. So what that means is on the job seeking side of things, recruiters, hiring managers, they're no longer scanning a resume asking is this a good csm? They're scanning a resume going, does this person solve the very specific thing that my team is looking for. Do they have all of the things I'm looking for? It's a completely different question. It's a completely different view of, of every single candidate. The problem is you've been solving for the first one. You've been trying to say I'm a good CSM M. That's not it. You need to be. I'm the specific CSM you're looking for for your organization. It's very different. So let's get into the nitty gritty things that do not work in this job market because of all of the things I just listed. Number one, waiting on referrals. Listen, I am not anti referral. Referrals are lovely, but thinking about the fact that you need to be a specific solution to some company's specific problem. Think about the math. For a referral to work, someone in your network has to know someone at a company that's hiring for a role whose specific needs actually matches you right now. And they need to be willing to make an introduction. The narrower those needs get, the lower the odds of a referral working gets. That's not me just crapping on referrals. That's just statistics. A very hyper specific market makes referrals less reliable. So I'm not saying ignore referrals, don't try to get referrals. What I am saying is if your sole strategy is to rely on referrals, it is going to take forever for you to land a job that way. Another thing that does not work in this job market is tweaking your resume to match job descriptions. I know if you're standing up right now, you might want to sit down for this one. If you're driving, you might want to pull over. Somebody somewhere said, hey, I've got an idea. The way that you land interviews is by stealing all the language from a job description and putting it into your resume. Match the keywords. This does not work, number one. It waters you down. By the time you've made yourself feel fit this job description, you are now just a generic CSM. And guess what? Your resume looks exactly like the 5000 other CSMs who also are doing the same keyword matching. So instead of differentiating yourself, all you've done is actually just say, hey, I'm the same as these other CSMs who are also plugging keywords from the job description into their resumes. I'm nothing special. I'm certainly not the specific CSM that you're looking for for your specific problem. Yeah, sit with that for a minute. The Other problem with shoving keywords into your resume is job descriptions are, I m don't want to say useless because that would be too strong of a word, but they're not the entire picture. As part of my role, I work with hiring managers who are looking for customer success managers and try to help them find CSMs. And 100% of the time when they send me the job description and I start poking holes in it, they say something to the effect of, yeah, so like, what's in the job description is not the full picture. There's actually all these other things that we're specifically looking for that are not in the job description. The reason for that, usually just laziness. Everyone's trying to do more with less. So when it comes time to open headcount, they go, let's grab that job description we used two years ago and throw that online. Anywho, back to my point about trying to match your resume to the job description, not only does it make you look like everyone else who's doing that, but now you're making yourself more look like something that's not even the full picture of the role. So you're trying to match your resume to this document and it's not even the right document because there's so much more that they're looking for that's not in the job description. Another thing that does not work in this job market is a volume approach. Mass applying using a reverse recruiter using these auto apply tools, which by the way, if you hire a quote unquote reverse recruiter, they're actually just shoving your resume into an AI tool that you could probably do for free or for like 10 bucks a month. So just keep that in mind. Anywho, volume is a great strategy in a market where everyone's just like, hey, I need a CSM with X years of experience. It is not the right strategy in this specific job market where everything is so specific it doesn't matter if your AI tool or reverse recruiter using an AI tool sends out 400 applications for you every single week. Because it's sending out 400 applications to 400 really specific, different unique needs. So that's just 400 misses. You just happen to get there faster than you would if you applied to those jobs on your own. I'm not just saying this because I am firmly against mass supplying the numbers. Back it up. Uh, we talk to a lot of the software companies who power these reverse recruiters or these like mass supply tools. They all say our, the people who use our platforms convert at 1%, one interview per 100 applications. Our clients who are not mass applying right now get at least an 8% interview rate, some up to 50, 60%. It's the same market. These are the same job postings. It's just a really different strategy. Okay, so now let's just talk about the pattern. I've talked about referrals. Not a great strategy. Tweaking your resume to match the job description. Not a great strategy. Mass applying. Not a great strategy. All three of these things are a solution to a visibility problem. They're all you just trying to get seen by as many hiring managers as possible. That sounds like it should work, but if you remember what's going on in this market, specific, specific needs, specific profiles. You don't need volume. You don't need to be seen by every single hiring manager in customer Success. You need to be seen by the right hiring manager who is looking for you specifically. You need to be the solution, uh, to their problem. So if you're spending all this time, all this energy, all this effort, trying to get seen by as many people as possible, you're really just, like, trying to solve the wrong problem harder and harder and harder. And that is exhausting in a way that I don't know if anybody's actually acknowledged for you. So let me say that's exhausting. It's not your fault if you've been doing this. It's just nobody's really told you what's going on, and so you're just doing, you know, what you've always been taught. But this is the moment where that changes. This is where you start to see, oh, uh, my gosh, you're right. I don't have a volume problem. I don't need to be seen by every hiring manager in cs. I only need to be seen as the specific solution to the specific problem for a few specific people. That's it. I just need to get in front of the right people. I've now watched well over 1200 customer success professionals hit this exact wall. My team and I have walked them through it, have shifted them from a volume play to a specificity play. And the ones who switch to specificity, they aren't sending more applications. They're not waiting for luck to strike them to get an interview. They get specific, and they get the interviews they want because it works. And by the way, this concept is no different from being a CSM who sells features versus a, uh, CSM who sells outcomes. We all know if you're a CSM who's talking about features. Features, features of your product or your software. The customer is not going to pay attention. Right? You need to get on the call with your customer and you need to say, hey, I know that you're trying to achieve this specific outcome. Let me show you exactly how to do that. You're not getting on that call going, hey, customer, here's our dashboard. Here's where you add this tag. Here's where you access the API. No, uh, we've moved on from that. We're not selling features, we're selling outcomes to problems. That is the shift, I'm telling you, you need to make in your job search. You need to stop selling yourself as a list of features that anyone could use. And you need to start being the solution to the problem. You need to start being what's going to get them their outcome. Now, this is a different concept, one that, uh, is probably the first time you're hearing this. So I want to make this a little bit easier to kind of like, chew on and understand. Especially if you're sitting there going, I don't know if I am trying to solve a volume problem or if I am being specific. You might not actually know. So here's what you're going to do. You're going to pause if you need to open a note on your phone, pull out a notepad, whatever. Try to answer this question. What is the specific thing you bring to the table better than other CSMs? It can't be I build strong relationships. It can't be. I'm customer obsessed. What is the specific combination of skills that you bring to the table that makes you different from other CSMs that you know? If you're sitting there looking at a blank note right now, I'm sorry to tell you that you have a specificity problem you have probably been trying to solve for volume, not specificity. That's why your resume gets ignored. That's why it doesn't get picked out of a pile. That's why if you are doing cold outreach to hiring managers, it's probably not landing. That's why you're mass applying. And maybe you're getting an interview here or there, but it's not for roles that you're excited about. And it is not because you are bad at your job. You're probably excellent at your job. That's what makes all of this so frustrating. A lot of it boils down to this concept of. If you've ever heard the saying, you can't read the label from inside the jar, you've Been inside your own career for however long. 4 years, 10 years, 15 years. It's really hard to see what makes you unique and different from where you're standing. You are inside the jar. So now the question is, okay, well, what the hell do I do about it? And I'm going to walk you through. There is a very specific sequence. There's three steps. We've now run over 1200 customer success people through this exact sequence, and it works. So I'm not going to try to cram it into, uh, the last two minutes of a podcast episode. If I rush it, it's not gonna work. And you're gonna walk away thinking this doesn't work, when really you just got a rushed version of it. So what I am going to do is walk you through this exact sequence tomorrow on July 30, Thursday, 12:30pm Eastern, in my live masterclass, how to land interviews for competitive customer success jobs. It is completely free. What we are gonna be doing on this masterclass, step one, we're going to find your position. We're going to do some reflection together, live. You are going to figure out what makes you unique and different and what specific thing you bring to this market that is going to help you find your position that is the foundation of everything else you do in your job search. The next thing we're going to do is I'm going to transform a real resume on screen. I'm going to show you how we take a resume from being generic to extremely specific. So you'll get to watch this in real time and of course, leave with a checklist of things that you can do on your own resume. Three, we are going to talk about outreach as a play on the hiring manager. This is the part that nobody else is teaching. And honestly, this is the thing that can completely change, uh, around your job search overnight. And of course, I've alluded to some things throughout this episode, like my work with hiring managers and how they've revealed things to me, like the job description isn't actually a description of who they're looking for. So I'll give you all the behind the scenes of what hiring managers are saying right now and give you all the information I've learned so that it helps you in your job search. This is live. There's going to be Q and A at the end. So. So come prepared with questions. And I promise you will not regret it. If you give me your time, if you give me an hour of your time, I promise I will make it well worth the hour. So grab your spot right now. Go to carlyagar.com landinterviews the, uh, link is also in the show notes, so you can grab the link there. And I'll see you tomorrow live on the master class.