A CS Hiring Manager Who Interviewed 3,000 CSMs Tells You What Gets You Hired (with Michael Boyd)
Aug 05, 2026
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Here’s what you can expect from this episode:
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 hiring managers actually evaluate technical skills, what they are really looking for during interviews, and what makes someone stand out in a competitive hiring process.
We also get into Michael's two out of three rule for landing roles that feel like a stretch, how to approach technical interviews with confidence even if you are not an engineer, and why AI fluency is becoming an expectation for every Customer Success professional. Most importantly, we talk about what has not changed and the skills that will continue to make great CSMs valuable no matter how the market evolves.
By the end of this conversation, you'll know what hiring managers are actually paying attention to, how they evaluate candidates, and how to position yourself as the kind of CSM companies want to hire. If you are ready to stop guessing what hiring managers want and start interviewing with more confidence, hit play and let's dive in.
And if you're tired of knowing you're qualified but not getting the offer, apply for coaching HERE and let's help you land your next Customer Success job.
Topics covered:
- Why the best hiring managers define success before they ever post a job
- How hiring managers actually assess technical skills even if you are not an engineer
- The simple two out of three rule that could change which Customer Success roles you apply for
- Why AI is raising the expectations for CSMs without replacing what makes them valuable
- What AI fluency really looks like in an interview and how to prove you have it
- The mindset shift that will help you stand out in today's Customer Success hiring market
Resources Mentioned:
When you’re ready, here’s how I can help you land a job in Customer Success despite all the competition:
- 1:1 Career Coaching Program – Get personalized support to land your first Customer Success role or finally step into your dream CS job.
- Free Training: Optimize Your Resume for Customer Success Jobs – Transform your resume so it gets noticed and starts bringing in consistent interviews.
- Free Training: Sell Yourself in Interviews – Learn exactly how to position yourself as the top candidate and walk into every CS interview with confidence.
- Free Training: Master Behavioral Interviews – Discover a proven method to answer every “tell me about a time” question and impress any interviewer.
Connect with Carly:
- Connect with me on LinkedIn
- Email me at [email protected]
Want more on this topic? Here’s your next listen:
- Episode 128: How To Impress a CS Hiring Manager (from a CS Hiring Manager) - with Eric Clouse!
- Episode 127: AI Won't Replace You as a CSM (But It Does Raise the Bar) - with Dan Ennis!
- Episode 123: 3 Things CS Job Seekers Waste the Most Time On (That Aren’t Getting Them Hired)
More about Customer Success Career Coach:
Customer Success Career Coach is the must-listen podcast for current and aspiring Customer Success pros. Join Carly and her guests as they spill the secret strategies and tips for building your Customer Success career. This isn't your typical snooze-fest – they’re diving deep into the world of Customer Success careers. Whether you're starting from scratch (hey career transitioners!) or eyeing that next big promotion, they’ve got the playbook for you. Every Wednesday, join Carly and her amazing guests as they dish out practical advice and real-life steps you can actually use. No fluff, just stuff you can apply ASAP to score that dream job, snag that promotion, or become the team rockstar.