How to land a CSM job tomorrow

Reality Check

Lets just call it like it is, its a blood bath out there in the SaaS job market. The ‘Growth at all costs’ mentally of 2019-2023 led to some incredibly bad behavior and the broader market suffered.

Maybe you were one of the casualties of this sh*t tornado or maybe you are just looking to break into tech.

Anyway you slice it, you are one out of literally hundreds of thousands of applicants.

So your real job is not applying but rather how to be 1 of 1.

The Mindset

There are something like 5,000+ open CS job listings out there yet I am willing to bet if you are reading this post, you still somehow can't seem to land an offer.

Why?

From where I sit, it comes down to Empathy (or lack thereof)…

When we are looking for a job, its all about us, our skills, our contributions, our needs.

“I would be a great fit for this role.”

“They have an open job listing, why wouldn’t they want to talk to me”

“I have so much to offer them if they could just give me a chance”

Me, me, me.

We need to break out of this self-inflection and start thinking through a lens of THEM.

The best way I have found to do this is to think about a ‘day-in-the-life’ of the other person.

For Example purposes, let’s build a fictional scenario & persona.

Let’s call this fictional persona is Kelly Kapoor - Director of Customer Success at Widget Inc.

Kelly was the first hire at Widget and by default, built out the CS program.

She never asked to be a Director, but she’s friendly, proactive and a problem-solver so it just kind of happened.

Widget has been growing and more and more customers are being put on the CS team’s lap.

Kelly’s normal week looks like:

• Net new Client onboarding kick off calls
• Check-ins on active accounts
• At-risk accounts to re-engage
• Customer tickets
• Requests from sales for additional support
• Requests from other teams to help with product and internal training
• Custom Enterprise account management request
• Requests from leadership for more granular churn and & retention reports

Her job can be summed up simply as: very busy.

Leadership comes to her and says “hey you look overwhelmed. Lets hire another CSM to work under you and take some of this work off of your plate.”

On paper this ‘sounds’ ideal. But then reality sets in.

Hiring means:

• job descriptions, workload calculations, management program, measurement
• qualifying, setting & running interviews
• onboarding, training & skill development program once hired

All this while trying to maintain the mountain of day to day work to keep the ship afloat.

With all this on her mind, Kelly has to sit on zoom calls with candidates (strangers) that all look the same on paper. Hard working, detail-oriented, customer-centric Customer success professional blah blah blah.

Kelly has to somehow scrape through the haystack to find a needle and hope that needle can actually help make her life easier.

Reputational Risk

Think about the risk Kelly has in hiring someone.. what if she picks the wrong person and they hurt the business? Kelly’s job could be in danger. This adds to the stress and pressure she feels to find the RIGHT candidate.

This is the reality for most CS folks trying to hire. Overwhelming to say the least.

Think about this next time you come into that interview thinking all about you, your needs, your future.

So if you are ever wondering why you don’t hear back or don’t get that offer, it is likely because Kelly is drowning.

What she doesn’t know how to ask, is for someone to step in and say “hey, I see you. I hear you. I’m here to help - let me show you.”

So what do you do?

The answer is, you need to:

SHOW you are the right fit not TELL.

99% of candidates are going to TELL.

Here is my resume, here is my story, here are my skills.

This puts all the work BACK on Kelly.

And as we have learned, Kelly doesn’t need more work on her plate.

The rest of this guide is going to show you practical examples of how you can take action and SHOW Kelly why you are obviously the right candidate for the job.

Regardless of the tactic, don’t forget - it’s about Kelly NOT about you.

Use Video

If there were one skill to develop in the modern working world, its comfortability on video. As a CSM, you are going to spend 75% of your time on video calls. Let a potential employer know you are confident and comfortable on video as it will directly relate to how you will come across to customers.

Employers are turning over their most valuable asset they have - their customers to you. They want to know that you can navigate conversations, assess painpoints, mitigate frustrations and jointly problem solve.

Being able to communicate on video is a secret weapon to standing out. As prevalent as video is in our day to day, very few people will actively seek out to record themselves on video when they could send text.

So here is the mindset shift: wherever you have something to share thats going to be more than 3 sentences, record a video.

Tools like: Loom, Vidyard, SendSpark, (even iorad ??)

They all have free trials that you can leverage.

Example

When filling out an application

Most applications have a series of open ended questions. They might ask you to describe yourself, your background and why you might be a fit for this position. This is a great use for video. Flip on your camera, show your warm, smiling face. Tell your story - let them get to know you BEFORE they ever met you. Imagine Kelly gets 250 applications for an open CSM role… maybe 5 people will take the extra step to stand out and use video.

Example video:

Try the Product

If the company is founder-led, odds are, the product is their baby. Few founders take on the brutal task of founding a company without a deep desire to solve a core problem. That means there is likely a strong culture of team members who really believe in the product/service. Showing you tried out and can speak towards using their baby, is a great differentiator.

Freemium products

If there is a free trial or free version of the tool, TRY IT. Sign up for a free trial, build out some examples, document your steps. Write out what you liked, didn’t like, where you see the tool being helpful.

Using iorad as an example, you can spin up interactive tutorials in seconds with our tool. Anyone in a few clicks could signup, make a few tutorials and share them. If someone wanted to stick out in the hiring process for us, they would send over what they created in a free account showing that willingness to go the extra mile.

Added Benefit

Leaders are all afraid of long, drawn out employee onboarding times. These have high costs and huge demands on the team. If you can show even an inkling that you get the product and can learn quickly, you are setting yourself apart. You are showing the employer that you aren’t going to need hand-holding at every moment of onboarding.

Example outreach:

“Kelly, heading into our interview next week just wanted to take a second to say how impressed I am with the product you and the team built. I signed up for a free trial, was able to [insert whatever value-prop the company has] really simply and easily. Can’t believe I am just now hearing about this tool. Anyway, here are a few examples of what I made in a trial account I played around with. Really excited to dive in in more detail!”

Audit of current Program

“Our Customer Success program is perfect, really needs no other tweaks” - No one.

Every team knows their program can use improvement. They are always works-in-progress and iterative by nature. CS teams are overworked and usually resource strapped. Sometimes suggested improvements from an outsider’s lens can be just the perspective they are looking for.

If you are truly an experienced CSM, SHOW them what you would bring to the table. Think of it like it was a free consulting call you are doing for them proactively. Take a look through their programming, help centers, Customer Academy, online resources and document out what you see (or don’t).

If they happen to have a free trial that you can access, spend some time studied their existing systems.

Ask yourself some questions and write down the answers. As a user:

• What feels unclear?
• Where are you confused or stuck?
• When and where do you feel like you would like some guidance?
• What examples and templates would feel helpful?

Spin up a document or video explaining your feedback while providing suggestions on what you would recommend. Write it like a report showcasing your expertise and where you feel like you would add structure and value.

Example:

***NOTE: Do NOT be judgmental here. The key is to lightly suggest WITHOUT blaming or scolding. This team has spent far more time than you have thinking through these problems. Making observations and broad suggestions is fine - but don’t go in acting like you have all the answers.

Negative Reviews / Dark Social

There is a lot of talk online about “dark social” - the conversations that happened around a brand that you are not apart of. Think: communities, slack channels, peer to peer communication. If a brand is carving a name out in a niche, odds are that niche is talking about that brand in some capacity. The key is to figure out how to influence the broader market so those conversations are positive and not reputation killers.

Bad reviews, bad experiences - these things spread like wild fire. As a CS professional, our jobs are to nail the customer experience so that positive word spreads about us.

One useful exercise to SHOW your value is to look into where and what is being said about the brand online and document it.

Check LinkedIn to see what the community is saying about the brand:

Positive Commentary

If you find customers or community members that are advocating for the brand, these would make for great testimonials or brand partners. Share with the hiring manager.

Ex:

“Kelly, not sure if you are the team are aware of [insert advocate]. They are sharing their experiences with [brand name] on social. They appear to be paying customers - one of the things I have seen be really helpful for the CS team is to reach out to those folks and ask them to do interviews and share their story as a case study. This really helps us in refining the brand story, use cases and workflows for our customers.”

Negative Commentary

If you find commentary online that is negative and detracts from the brand, you can also call that out and explain how you would reach out and try to solve for that.

Example:

Portfolio > Resume

Resumes do a terrible job of telling good stories and examples of a person’s skills & potential. Listing out chronologically the roles and bulleted responsibilities you held won’t SHOW the employer much.

Where possible, reposition your resume as a portfolio documenting your impact instead of a boring resume.

Remember - Kelly is busy and she is under a lot of pressure. Looking at a stack of resumes, she doesn’t want to stick her neck out and put her fate in the wrong hire.

SHOW her how you helped in your previous roles and that you are the obvious fit.

Examples:

Use tools like Canva, Wix, SquareSpace, Notion, Adobe, Figma - they all have free templates that you can use to whip up a portfolio sites in an afternoon.

Structure

Describe your experience as if it was a movie script.

• What was the before state (with details)
• What was the desired outcome
• Who were the main characters
• What did you contribute
• What programs and processes did you instill
• What was the outcome (metrics and details help)
• What would you do differently

SHOW what you did in a project breakdown format that is easy to consume.

Bonus points for using video to explain and showcase examples.

LinkedIn Presence

If you want to stand out from the sea of other candidates, you need to be top of mind as much as possible. A quick win for this is to follow and engage with the brand’s content as much as possible.

LinkedIn content is a great magnifying glass into how the company speaks, what they care about and how they function.

Go and follow all the content creators at the company like and engage with their content. The key is to be intentional and thoughtful in your responses. Don’t just use generic messaging. Write comments that show how you think and showcase your subject matter expertise.

Example guide:

Tech Stack Experience

We know brands are very conscious about long, painful & costly employee onboarding. They are worried about having to train people from scratch. A LOT of what modern work is now is living inside software tools. Because of this, existing experience is a huge plus in a candidate. Specifically around tech stack.

SHOW you have expertise in their tech stack. Listing “proficient in Excel” is no longer cutting it. If the job posting says they use HubSpot CRM - explain your experience with it.

Don’t share anything proprietary but document what projects and programs you used that tool for. Brands are always interested in improving how they use the technology they have invested in.

Examples, explainers and mock ups help SHOW why you are going to be a dream hire.

The same is true for any technology or industry related experience you may have. Don’t just talk about it, SHOW IT in any tangible way you can.

Document 30, 60, 90 day plan

Leadership is going to want to know what kind of impact they can expect from hiring you for this role. Instead of telling them, SHOW them in the form of a strategic plan. The goal here is to give them insight into how you think. Odds are, leadership already has a plan. Its not about being perfectly aligned with that plan as much as it is SHOWING you were willing to sit down and put the time in to work strategically.

Write out a detailed overview for a 30, 60 and 90 day action plan. This should be highly relevant to their business, including objectives and initiatives they described in their job application and any information you gleaned online.

**YES, you can use AI to help you assemble an outline but I would recommend just that an “outline”. You should be taking an outline and catering it towards the nuances of their business.

Example:

30, 60, 90 day plan example

Get Referrals

Nothing is better than a recommendation from a peer that you respect. A great play is to get others to recommend you to the hiring manager.

Here is an approach for doing that:

Mutual Connections

Example:

*“Hey Tim, do you happen to know Kelly Kapoor at Widget? They are hiring for a CSM and I think it could be a great opportunity for me based on my experience. If so, had a huge favor.. based on our experience together at ABC company, would be willing to shoot Kelly a message and recommend me. Something like:

Hey Kelly, saw you are hiring for a CSM. Not sure if you know Sean Adams but he would be a great candidate for this. I worked with him at ABC and he was great at [insert valuable skill and intangibles]. Would highly recommend checking him out if you haven’t spoken to him already.”*

This sort of third party validation can be huge for making you stand out from the crowd.

Wrapping it All Up

Hopefully by now you see how impactful it is to go the extra mile, seeing the world from the hiring manager's perspective and deciding that your future is worth this level of creativity.

Know this: creative, personalized service like this is exactly what high performing CSMs do in their day to day.

Quality inputs = quality results.

With all this said, there are still going to be jobs that you apply for with this level of effort and STILL get ghosted by. That is just the nature of where we are... do not let it beat you down!

Its all worth it! If nothing else, you are sharpening your skills for when that perfect job happens.

PS - we are hiring a CSM at @ iorad, if any of this resonated, you now have a playbook on what to do.