Inspired by Episode 12 of the Doing It for Retention Podcast
Your CV could list a £100 million book of business, ten years of customer success experience, and every SaaS tool known to humanity. But if you’ve addressed your application to the wrong person, sent it through the wrong channel, or failed to demonstrate you’ve spent even two minutes researching the company, you won’t get an interview.
This isn’t about credentials. It’s about intention. And hiring managers can spot the difference immediately.
The Cover Letter Isn’t Dead
Despite what some career advisors claim, cover letters matter. Not the corporate-template variety that regurgitates your CV in paragraph form. The authentic, personality-driven kind that shows there’s an actual human behind the application.
When applications come in via email, the covering letter is often the email itself. It’s your first impression. It’s your chance to demonstrate that you’re not a robot blindly firing applications into the void.
Hiring managers read these first. Before opening your CV. Before looking at your credentials. They want to see if there’s a person worth talking to.
What makes a covering letter work? Authenticity. Personality. A clear demonstration that you’ve actually looked at the company and the role. You don’t need to write a novel. You need to write something that sounds like you, not like ChatGPT.
The Honesty Strategy That Actually Works
Here’s a covering letter approach that gets attention: brutal honesty.
“I’ll be straight with you, on my CV, you won’t find a customer success title. But I assure you I’ve been doing CS work by managing [specific responsibilities]. Here’s how my experience translates to what you need…”
This works. It demonstrates self-awareness, it shows you’ve actually read the job requirements, and it proves you’re willing to address potential concerns head-on rather than hoping nobody notices.
Compare that to sending a generic CV and hoping the hiring manager connects the dots themselves. Which approach do you think gets the interview? Honesty combined with specificity is a powerful combination. It shows confidence without arrogance, and awareness without insecurity.
The Name on the Application Matters
Getting the hiring manager’s name wrong is a death sentence for your application. Not a misspelling, an entirely different name. Tyler instead of Stijn. Matthew instead of Sarah. This happens more often than you’d think.
It doesn’t matter if you have the perfect experience. If you can’t be bothered to double-check who you’re applying to, you’re signalling that attention to detail isn’t your strong suit. And attention to detail is pretty fundamental to customer success.
This seems obvious. Yet it continues to happen with depressing frequency. Take the two seconds to verify you’ve got the right name. It’s the easiest way to avoid an automatic rejection.
Numbers Without Context Are Meaningless
Your CV lists impressive metrics. You increased NRR to 120%. You managed a £10 million book of business. You improved response rates by 75%.
None of this matters if you can’t explain how you did it.
Customer success isn’t a solo sport. You don’t achieve outcomes in isolation. You collaborate with sales, marketing, product, and operations. You build strategies that require cross-functional alignment. You navigate company politics and competing priorities.
The hiring manager doesn’t just want to know what you achieved. They want to know how you work with others to achieve it.
“Increased NRR to 120% by collaborating with marketing to build a customer advocacy programme that drove referrals and expansions”. That’s interesting. That tells a story. That suggests you understand business development and cross-functional collaboration.
“Increased NRR to 120%”. That’s just a number. And numbers can be exaggerated, misrepresented, or entirely fabricated. There’s no way to verify them, so they carry less weight than you think.
The Collaboration Question
If your CV is entirely focused on your individual achievements without any mention of how you worked with other teams, you’re missing the point of what modern customer success actually is.
CS sits at the centre of the organisation. You need sales to bring customers in. You need product to build features that solve problems. You need marketing to amplify success stories. You need support to handle technical issues.
If you’re presenting yourself as a lone wolf who single-handedly drove results, you’re either lying or you were never actually doing customer success in the first place.
Show how you collaborate. Mention the teams you worked with. Explain the processes you built that required buy-in from multiple stakeholders. This demonstrates maturity and business understanding that pure metrics cannot capture.
The “Why This Company?” Question
Every interview includes some version of “Why do you want to work here?” It’s not original, but it’s still important. And candidates consistently fail to prepare for it.
The bare minimum is visiting the company website and reading one article about them. That’s it. That’s the floor, not the ceiling.
Better candidates go further. They understand the market the company operates in. They’ve looked at the product, maybe even signed up for a free trial. They can speak knowledgeably about what the company does and why it’s interesting to them specifically.
The best candidates connect their previous experience to the company’s current challenges. “I noticed you recently secured Series B funding. I went through a similar growth phase at my last company, and I understand the CS challenges that come with rapid scaling. I’d love to bring that experience to help you navigate that transition.”
This isn’t difficult. It just requires actually caring about the opportunity rather than treating it as one of 50 applications you’re sending this week.
The Application Channel Matters
If the job description says “apply via email,” don’t send a LinkedIn DM. If it says “no phone calls,” don’t call. If it specifies a particular email address, use that one, not the general company info address.
This seems trivial. It’s not. It’s a test of whether you can follow basic instructions. And in customer success, following customer instructions whilst delivering value is pretty much the entire job.
When hiring managers specify application methods, they have reasons. Maybe they’re trying to keep applications organised. Maybe they want to see how candidates handle email communication. Maybe they just want to reduce inbox clutter from 15 different channels.
Whatever the reason, ignoring the specified process signals that you think the rules don’t apply to you. That’s not the impression you want to create.
The Personality Filter
Here’s what many candidates miss: hiring managers are trying to answer two questions. Can you do the job? And would I want to work with you?
The first question is about credentials. The second is about personality. And personality shows up in every interaction from the first email onwards.
Are you professional without being robotic? Can you demonstrate enthusiasm without being over-the-top? Do you come across as someone who’d be pleasant to work with on both good days and bad days?
If you’re sending template applications with no personality, you’re failing the second test before you even get to demonstrate your qualifications.
Customer success requires emotional intelligence. Show some in your application.
The Trust Question
One question hiring managers ask themselves after every interview: “Would I trust this person with our customers if I was on holiday?”
You could have twenty years of experience and manage millions in revenue. But if you come across as arrogant, difficult, or unable to take feedback, the answer is no.
Customer success requires emotional intelligence, resilience, and the ability to build relationships with diverse personalities. If you can’t demonstrate these qualities in the hiring process, why would a manager trust you to demonstrate them with customers?
Think about what you’re signalling in every interaction. Your email tone. How you respond to questions. Whether you’re defensive or open to feedback. All of it matters.
The Five-Minute Research Rule
Every successful application strategy comes down to this: invest five minutes of research before you hit send.
Look at the company website. Understand what they do. Check the hiring manager’s LinkedIn profile, not to stalk them, but to understand their background and communication style. Read the job description carefully. Tailor your covering letter to reference something specific about the company or role.
Five minutes. That’s the difference between an application that gets ignored and one that gets read properly.
Those five minutes signal that you’re treating this as a specific opportunity, not just another number in your spray-and-pray strategy. And that signal matters more than almost anything else in your application.
The SaaS Mindset Applied to Job Applications
If you work in customer success, you work for a SaaS company. Think about how SaaS companies market themselves.
They don’t overwhelm you with information. They give you enough to spark interest. They show social proof through testimonials and case studies. They make it easy to take the next step with clear calls-to-action.
Your CV and covering letter should work the same way. Give enough information to spark interest. Show results through specific examples. Make it easy for the hiring manager to see why they should interview you.
Don’t write a five-page CV that nobody will read. Don’t bury your best achievements in dense paragraphs. Think like a marketer presenting a product – make it scannable, interesting, and action-oriented.
What This All Comes Down To
The candidates who get interviews aren’t necessarily the most qualified on paper. They’re the ones who demonstrate intention, personality, and genuine interest in the specific opportunity.
They’ve done their research. They’ve followed instructions. They’ve shown they understand what the role actually involves. They’ve presented themselves as humans, not just lists of accomplishments. This doesn’t require extraordinary effort. It requires consistent, intentional effort across every application you send. Five minutes of research. A personalised covering letter. Getting the hiring manager’s name right. Following the stated application process. Explaining how you achieved your results, not just what you achieved.
These small things compound into a massive advantage over the hundreds of other applications that ignore them.
The hiring market is competitive. Customer success roles attract enormous numbers of applicants. You can’t control that. But you can control whether your application demonstrates that you’re worth paying attention to.
The question is: are you willing to invest the effort to stand out? Because if you’re not, don’t be surprised when your applications disappear into the void.
About ABR Talent
ABR Talent specialises in connecting exceptional professionals with leading SaaS companies. Whether you’re making your first move into tech or seeking your next leadership role in customer success or sales, we understand the unique challenges and opportunities in the market.
Get in touch to discuss your career journey or hiring needs.
