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

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 t...

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 time that ...

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 can cost you the offer, a...

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 share the AI term...

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 simple change that makes you stand...

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 t...

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...

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...

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 feel...

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 ...

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 the biggest mistakes job seekers an...

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 that make strong candidates come acr...

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 cover why memorizing answers is actua...

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 ones created the most momentum.

In this...

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, why some “good&rdqu...

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 career, why most CSMs are...

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-step frame...

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 hiring managers to...

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 numbers, and how to think ab...