Customer Success Career Coach

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 competition is snoozing.

I’ll walk you...

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 what to skip), how to use resource...

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 every department wants on their team. W...

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 without obsessing over her resume or ...

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 talent acquisition pro, to dissect exac...

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 you noticed by the people who actuall...

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 strategic coaching makes, and the...

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 answer transformations (from bland to...

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 scratch), the “invisible work”...

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-figure Customer Success offer (with ...

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. 

You’ll learn why memorizing...

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 outreach secrets. I’m revealing the...

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 you’ve heard about content creation...

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 solutions that hiring managers despe...

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 and hand you my simple 3-step fram...

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 to start” to “wait… this is actuall...

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’re not using… but should be. We unpa...

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 behaviors that got them hired and the su...

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, and resume tweaks that turned the...