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

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...

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...

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...

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 QBR...

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...

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’...

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 beha...

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, mindse...

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...

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...

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...

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...

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 frame...

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 t...

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 optimi...

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...

Ever walked out of an interview wondering, “Did I ask the right questions?” “Did I get all the information I really needed?” Let’s make sure you never feel that way again. In this episode, I’m giving you ten power questions that’ll help you stand out, impress hiring managers, and get the real intel you need to make smart career moves. We’re ditching the generic “What are the next steps?” and repla...

Ever walked out of an interview thinking, Did I sound too stiff? Was I awkward? Why didn’t I click with the interviewer? Interviews aren’t just about saying the right things. They’re about connection. If you’re so focused on being “perfect” that you forget to sound like yourself, you might be holding yourself back. In this episode, I’m sharing seven actionable tips to help you sound more natural,...

Ever walked into a new job thinking it was the one , only to realize you just stepped into a nightmare? Let’s make sure that NEVER happens to you. In this episode, I’m breaking down seven major red flags you cannot ignore when searching for your dream Customer Success role so you don’t end up in a job that makes you miserable. I’m joined by Bri, one of our amazing coaches inside Carly Agar Trainin...

If there is one certainty in your customer success career, it is this: things will change. Whether it's new initiatives, restructuring, or evolving processes, staying ahead is non-negotiable. In this episode, I am breaking down exactly how to handle the constant change that comes with being a CSM. Think of this episode as your tactical guide to staying ahead. If change has you overwhelmed and you...

Do you think the only way to advance your customer success career is through job-hopping? It’s time to rethink that approach because I'm going to show you how to make a strategic internal career move. In this episode, I'm breaking down exactly how to create your dream role without even leaving your company. I’ll share my personal blueprint – the exact steps I took to make this internal career move...

Are you unintentionally blocking your own path to opportunities like promotions, transitioning to different teams, managing larger accounts, engaging in cross-functional projects, or securing a raise? If you're not progressing in your customer success career as you'd hoped, the answer might be yes. In this episode, I'll explain how you could be unintentionally stalling your customer success career...

Would you believe that a single 30-minute coaching session could lead to a $215K job offer? That's precisely what happened to one of our recent clients, and I'm thrilled to unpack this incredible story for you. In this episode, I'm taking you behind the scenes to reveal how one coaching session transformed my client’s approach to interviewing and led her to a $215,000 job offer, all by refining th...

Are you ready to impress at your next CSM interview presentation? If you haven’t listened to part one, I recommend you go back and listen to that one first, but in this part 2, I am letting you in on six sneaky things you can do in your next CSM interview presentation to wildly impress the hiring team and get that offer. Tune in to learn how to master your content delivery, engage your audience, s...

Do you dread the thought of a CS interview presentation? People love to hate these, but not me! That’s why, in part one of this two-part series, I am diving into how to nail your CS interview presentations. I’ll share everything I have learnt from my experience as a hiring manager and a coach who has helped over 800 aspiring professionals. I’ll break down the three most common types of presentatio...