What to do when you’re “stuck”

Job searching can feel like running into the same wall repeatedly. You've got solid experience, you're putting in the work, but something's not clicking. This guide will help you identify exactly where you're getting stuck and provide specific actions to break through.

Finding Out Where You're Stuck

Before we jump into solutions, let's figure out exactly where things are breaking down. Think of your job search like a funnel - applications lead to screens, screens lead to interviews, and interviews lead to offers. Where are you getting stuck in this funnel?

Before diving into solutions, let's understand what's different about today's CS job market:

Current Market Challenges:

• Companies are seeing 300+ applications per role, often from experienced CSMs

• Many companies have sophisticated ATS (Applicant Tracking Systems) that screen resumes

• Hiring managers are looking for more technical and data-driven CSMs

• Remote roles face even more competition due to expanded candidate pools

What This Means For Your Search:

• Your application materials need to be exceptionally strong

• You need both volume and targeting in your approach

• Network and referrals matter

• Standing out requires demonstrating concrete business impact

Not Getting Any Responses to Your Applications?

This is one of the most common problems I see, and it usually means one thing: your application isn't telling the right story. Here's what's likely happening:

Think about what hiring managers care about most - they want to know if you can make their customers successful and help their business grow. But many CSM resumes focus on the wrong things. Instead of saying "I managed customers and ran QBRs," they want to hear "I helped 25 enterprise customers grow their spend by 40% last year through strategic account planning."

Here's what your resume probably needs more of:

• The size of your impact (like "managed $5M in ARR" instead of just "managed enterprise customers")

• Real numbers showing success (think retention rates, growth numbers, customer satisfaction scores)

• Technical skills you've used (specific tools, automation you've built, processes you've improved)

• Examples of problems you've solved (like turning around struggling accounts or scaling customer programs)

Your job search strategy might also need some tweaking. I often see CSMs making their search too narrow or too broad. For example, if you only apply to big tech companies (like Google or Facebook), you compete with hundreds of other applicants. Meanwhile, you might miss great opportunities at growing companies where your experience would be even more valuable.

The other common reason is that you just aren't applying to enough jobs. Yes, it sucks and is sometimes time-consuming, but this is today's reality. Re-visit our previous guide and bump up the number of applications you submit each week.

Getting Initial Interviews But Not Moving Forward?

If you're getting those first calls but not advancing, we need to work on your storytelling. This is where I see a lot of experienced CSMs struggle - they know their stuff, but they have trouble explaining it in a way that shows their strategic thinking and paint a compelling and clear picture.

Let me give you an example of what great storytelling sounds like in a CS interview:

"Last year, I noticed one of our biggest customers wasn't using our product as much as they should. Instead of just doing more check-in calls, I dug into their usage data and found that only half their team had completed training. I put together a 90-day plan that included custom training sessions, weekly progress tracking, and regular check-ins with their leadership team. Three months later, their usage was up 80%, and they ended up doubling their contract with us."

See how that story shows both what you did AND how you think? That's what interviewers are looking for. They want to know you can spot problems, come up with smart solutions, and measure the results.

Common places where people get tripped up in interviews:

• Talking about what they did without explaining why they did it

• Not having specific numbers to back up their successes

• Focusing too much on day-to-day tasks instead of bigger strategic wins

• Not connecting their past experience to what the new company needs

• Being unable to tell a cohesive story that has a logical sequence of events

• Not being able to different themselves from other CSMs

Making It to Final Rounds But No Offers?

This is often about showing you can think at a higher level. By the final rounds, they know you can do the job - now they want to see if you can help shape the future of their customer success program.

Getting More Responses to Your Applications

Let's talk about how to get your application to stand out in a crowded field. Think of your application as your professional story - you want to make it impossible for hiring managers to pass up.

Making Your Resume Tell a Better Story

Remember how we talked about showing impact instead of just listing tasks? Let me show you how to transform your resume bullet points. Here's a real example I worked on with a CSM:

The original bullet point read: "Managed enterprise customer portfolio and conducted quarterly business reviews."

We changed it to: "Led strategic planning for $12M portfolio of enterprise accounts, achieving 118% net revenue retention through data-driven QBR program that identified expansion opportunities worth $3.2M."

See the difference? The second version shows the scale of what you managed ($12M portfolio), the results you got (118% retention), and how you did it (strategic planning and data-driven QBRs). That's the kind of detail that makes hiring managers want to learn more.

Let's practice transforming another common CSM bullet point. Instead of "Helped customers adopt new features," you might write: "Developed targeted adoption program for key product features, increasing average feature usage by 65% across 50 enterprise accounts and driving $800K in expansion revenue."

Being Smart About Where You Apply

Getting more responses isn't just about having a great resume. It's also about applying to the right roles at the right time. Think of it like fishing…you want to fish where the fish are biting.

Here's what I mean: Let's say you've got experience building customer success programs from scratch. Instead of only applying to big companies with established CS teams, look for fast-growing companies that are just starting to build out their CS function. They're more likely to value your experience building things from the ground up.

Or maybe you're great at handling complex enterprise customers. Look for companies that are just starting to move upmarket. They're often desperately looking for people who know how to handle bigger, more complicated accounts.

When you find a promising company, here's a trick that works really well: Look them up on LinkedIn and check if they've recently raised funding or if they're growing quickly. Companies that just raised money are usually hiring aggressively, and your application is more likely to get noticed.

Making Your Network Work for You

Let me bust a common myth: networking isn't about having hundreds of LinkedIn connections or going to every CS meetup. It's about building genuine relationships with people in your field. Here's a strategy that works much better than cold applying:

Find a company you're interested in and look for people in their CS team. Maybe they've written articles about their CS approach or spoken at conferences. Reach out and say something like: "I really enjoyed your article about scaling CS teams. I'm currently handling similar challenges in my role and would love to hear more about your experience."

Notice how we're not asking for a job; we're starting a real conversation about shared professional interests. These kinds of connections often lead to job opportunities naturally, and even when they don't, you're building relationships that will help you throughout your career.

Making Your Application Process More Efficient

Here's a secret that most people miss: treating your job search like a CS project can make a huge difference. Just like you track customer health metrics, you should track your application metrics.

Create a simple spreadsheet to track:

• Which companies you're applying to

• How you found each opportunity (job board, referral, direct outreach)

• When you applied and followed up

• The results you're getting

This data will tell you what's working and what isn't. Maybe you'll notice you get better responses from companies you find through LinkedIn than through job boards. Or you might see that applications you submit within 24 hours of a job posting get more responses than older postings.

Moving from Conversations to Offers During Interviews

Getting interviews shows your application strategy is working. Now let's focus on turning those interviews into job offers. As interviews get more challenging in later rounds, they're really looking to see if you can think strategically about customer success and help shape their company's future.

Telling Stories That Show Strategic Impact

Think about how your role as a CSM has evolved. In the beginning, success meant making individual customers happy. But as you've grown, you've learned to think bigger – how to make entire segments successful, how to scale programs, and how to drive business growth. This evolution in your thinking is exactly what companies want to see, especially in later interview rounds.

Creating Your Talk Track

Your talk track should weave together:

• Your unique journey into customer success

• Specific challenges you've overcome

• Problems you love solving

• What drives you to help customers succeed

• Your philosophy about customer success

Let me show you the difference. Here's how most CSMs talk about handling challenging customers: "I had a frustrated enterprise customer, so I increased our check-ins and provided more training. They became much happier and renewed their contract."

While that's fine, it focuses just on tactical execution. Here's how to tell that same story with strategic thinking: "I noticed several enterprise customers struggling around the same time in their journey. Rather than just treating symptoms, I analyzed data from our last 20 enterprise customers and discovered those who didn't complete certain technical integrations within 60 days were three times more likely to churn. I used this insight to rebuild our onboarding process, prioritizing these crucial integrations early. This systematic change reduced time-to-value by 40% and improved year-one retention across all enterprise accounts by 25%."

See the difference? The second version shows you can spot patterns, use data to find root causes, and create scalable solutions that improve business metrics. That's the kind of thinking that gets job offers.

Making Memorable Connections

The First Five Minutes Matter

Research shows interviewers often form initial impressions in the first few minutes. Make them count:

Building Genuine Rapport:

• Research your interviewers beforehand

• Find authentic common ground

• Show genuine curiosity about their challenges

• Share relevant insights about their company

• Use their language and terminology

Going Beyond Basic Research: "I noticed your company recently launched [feature]. This resonates with me because in my current role, I helped customers through a similar transition by..."

Handling the Technical Deep Dive

As CS becomes more technical, you'll face questions about tools, systems, and data analysis. Don't worry – you don't need to be a software engineer, but you should show how you use technology to scale customer success.

Instead of just listing tools you've used, explain how you've used them to solve real problems. For example: "Our team was spending hours manually checking customer health metrics. I saw an opportunity to automate this using Gainsight. I built a system that combined product usage data, support tickets, and engagement metrics to create health scores that automatically triggered different playbooks. This saved our team 15 hours per week and helped us catch at-risk customers twice as fast."

This answer works because it shows you can identify operational challenges, use technology to solve them, create systematic approaches, and measure the impact of your solutions.

Connecting CS to Business Growth

In final rounds, you'll often talk with senior leaders who care most about business impact. They want to see that you understand customer success as a driver of growth, not just a support function.

When discussing your experience, connect it directly to revenue and growth. For instance: "While our customer satisfaction was strong at 85%, I noticed our expansion revenue was below industry benchmarks. By analyzing our successful expansions, I identified three product features that predicted account growth. I created a program focusing on driving adoption of these features, resulting in a 40% increase in expansion revenue while maintaining our satisfaction scores."

This shows you can balance customer happiness with business growth – a crucial skill for senior CS roles.

Demonstrating Your Ability to Scale

One question that often comes up in final rounds is how you'd scale customer success as the company grows. This is your chance to show you think about CS beyond managing individual accounts.

Share examples of how you've helped scale CS operations. Maybe you created templates that helped new CSMs ramp up faster, or developed a tiered service model that let your team handle more accounts efficiently. The key is showing you can think about customer success at a program level.

For instance: "When our customer base grew from 100 to 400 accounts in one year, I realized our high-touch model wouldn't scale. I analyzed our customer segments and created a tiered service model. Enterprise accounts kept dedicated CSMs, while we moved smaller accounts to a pool-based approach supported by automated onboarding and self-service resources. This let us maintain our retention rates while tripling our customer coverage per CSM."

Practice Makes Perfect

Before your interviews, practice telling your strategic stories out loud. Focus on:

• Setting up the context clearly but briefly

• Explaining your thought process and analysis

• Highlighting cross-functional collaboration

• Sharing specific metrics and results

• Connecting your actions to business outcomes

Remember, companies aren't just hiring for what you've done – they're hiring for how you think and solve problems. Show them you can not only execute well but also think strategically about scaling customer success.

Optimizing Your Job Search by Running Smart Experiments

Let me change how we think about the job search process. Instead of choosing between quality or quantity, we're going to do both - treating your job search like a systematic experiment while maintaining high volume. Think of it like running A/B tests for a large customer base.

Setting Up Your Testing Framework

First, let's create a system for tracking everything. Just like you'd track customer behavior across different segments, you'll track your application performance across different approaches.

Create a spreadsheet with these key columns:

• Company name and role

• Resume version used (A, B, C, etc.)

• Application date and method

• Response (yes/no)

• Days to response

• Interview stages reached

• Feedback received (if any)

• Notes on what resonated in interviews

Now, let's run multiple experiments simultaneously while maintaining volume.

Running Resume Experiments

Think of your resume versions like different onboarding flows you might test with customers. Start with three versions:

Version A (Control): Your current resume that follows best practices:

• Clear metrics

• Impact statements

• Technical skills

• Portfolio size

Version B (Strategic Focus): Emphasize strategic initiatives:

• Program building

• Process scaling

• Cross-functional leadership

• Business impact

Version C (Technical Depth): Highlight technical expertise:

• Platform customization

• Automation creation

• Data analysis

• Integration experience

Apply to at least 30-40 jobs per week, evenly distributing these versions. Just like with customer testing, you need a large enough sample size to draw meaningful conclusions.

Testing Interview Talk Tracks

Similarly, prepare multiple versions of your stories for interviews. For the common "tell me about a challenging customer" question, test different frameworks:

Framework 1 - Problem Solver: "When I inherited our largest account, they were at risk of churning. By analyzing their usage patterns..."

Framework 2 - Strategic Thinker: "I noticed a pattern across several enterprise customers struggling with adoption. After analyzing data from 20 accounts..."

Framework 3 - Business Impact: "While managing a $10M portfolio, I identified an opportunity to improve expansion rates. By focusing on..."

Track which stories and frameworks get the best responses in different interview stages.

Analyzing Your Results

Review your data weekly:

1. Calculate response rates for each resume version

2. Note which stories advance you further in interviews

3. Identify patterns in feedback

4. Adjust your versions based on what's working

For example, you might find:

• Version B gets more responses from growth-stage companies

• Framework 2 resonates better in final rounds

• Technical depth stories work best with engineering-heavy companies

Making Data-Driven Adjustments

Just like you'd optimize a customer journey, continuously refine your approach:

If Version B is performing best:

1. Create Version D incorporating its best elements

2. Add more strategic examples

3. Adjust formatting to emphasize key metrics

4. Test against Version B for another cycle

Meanwhile, maintain your application volume. The goal is to optimize while still getting enough data points to make informed decisions.

Volume + Quality Strategy

Here's how to maintain both:

• Spend 1 hour each morning applying to new postings (high priority)

• Block 2 hours in the afternoon for more applications

• Use saved job searches and alerts to find new postings quickly

• Create templates for common application requirements

• Track your most effective job boards and focus there

• Set daily minimums (8-10 applications) and weekly targets (35-40)

Remember: Just like you wouldn't stop acquiring new customers while optimizing your onboarding, don't slow down applications while you're testing different approaches.

Key Success Metrics

Track these numbers weekly:

• Total applications submitted

• Response rate by resume version

• Time to response

• Interview conversion rate

• Stories that advance you to next rounds

• Overall pipeline health (applications in process)

This data-driven approach lets you maximize both quantity and quality, increasing your chances of finding the right role while continuously improving your materials and approach.

FAQs

Q: I know I'm qualified for these CSM roles, but I'm not getting any responses. I have experience - why aren't companies seeing my value?

A: Let me help you think about this differently. In today's market, being qualified isn't enough - you need to make your unique value impossible to miss. Think of it like when you're trying to get a customer's attention in a crowded marketplace. You wouldn't just tell them "we have good customer support" - you'd show them specifically how you solve their biggest problems.

The reality is that companies are getting hundreds of applications for each CS role, often from people with solid experience. But here's the thing - many of those applications look remarkably similar. They all talk about managing customers, running QBRs, and improving retention. To stand out, you need to tell a more compelling story about what makes your experience special.

Let's look at how to do this effectively. Instead of just saying you're qualified, think about what makes your journey and impact unique:

Did you build something from scratch? Maybe you created the first customer health score system at your company, transforming how the team identified at-risk customers. That shows you're not just a manager but an innovator.

Have you solved complex problems? Perhaps you found a way to scale customer onboarding when your company grew from 50 to 500 customers in a year. That demonstrates you can handle rapid growth and create scalable solutions.

What about measurable impact? Don't just say you improved retention - tell them how you analyzed customer data to identify key adoption patterns, then built a program that increased net revenue retention from 100% to 115% across a $10M portfolio.

Here's how to make your unique value clear:

• First, look carefully at each role you're applying for. What specific problems is this company trying to solve? Are they scaling rapidly? Moving upmarket? Building their CS function from scratch? Then connect your experience directly to their needs.

  • And yes, it is a numbers game - but that doesn't mean sending the same application to 100 companies. Instead, create 3-4 versions of your resume, each highlighting different aspects of your experience. Maybe one focuses on your enterprise experience, another on your program-building skills, and a third on your technical expertise.

• Then apply widely, but thoughtfully. Target 30-40 applications per week, mixing different types of companies and roles. Track which version gets better responses from which types of companies. You might find that highlighting your experience building processes from scratch gets more responses from Series B companies, while emphasizing your enterprise account management resonates better with larger organizations.

Think of it like running multiple customer acquisition campaigns simultaneously - you're testing different messages with different segments, while maintaining enough volume to get meaningful data. Remember, in this market, your goal is twofold: make your unique value crystal clear AND get your application in front of enough companies to find the right match. Don't get discouraged if it takes time - focus on continuously refining how you communicate your value while maintaining a steady volume of applications.

Q: I'm getting interviews but they keep picking candidates with more technical skills. Should I only apply to less technical CSM roles?

A: Let me help you reframe this challenge. The solution isn't to limit your opportunities - it's to better communicate and potentially expand your technical capabilities. Many CSMs actually have more technical experience than they realize; they just aren't presenting it effectively.

Think about your daily work. You likely use various platforms and tools to manage customers, analyze data, and automate processes. That's technical experience, even if you don't think of it that way. The key is explaining how you use these tools to drive business outcomes.

For example, instead of just mentioning you use Gainsight, explain how you built automated workflows that helped your team identify at-risk customers two weeks earlier than before. Or instead of saying you're familiar with Salesforce, describe how you created custom reports that helped your team prioritize expansion opportunities, leading to a 30% increase in upsell revenue.

Here's a concrete way to demonstrate your technical capabilities:

When you discuss your experience with CS platforms, walk through a specific project. For instance: "I noticed our team was spending too much time manually tracking customer health. I used Gainsight to build an automated scoring system that combined product usage data, support ticket trends, and engagement metrics. This not only saved our team 10 hours per week but also helped us identify at-risk customers 40% faster."

If you want to strengthen your technical skills, here's a practical approach:

Start by mastering the tools you already use. Most CS platforms have certification programs or advanced training. Spend a few hours each week diving deeper into features you might not regularly use. Build something new in your current role - maybe an automated workflow or a custom dashboard.

But remember, volume still matters. Keep applying to roles across the technical spectrum while you build these skills. Many companies value potential and learning ability as much as current technical expertise. Focus on showing how you've learned and applied new technical skills throughout your career.

The goal isn't to become a software engineer - it's to show you can use technology effectively to scale customer success. Keep track of which types of roles and companies respond best to your current technical experience, and use that data to refine both your applications and your learning focus.

Q: "Every job description asks for experience with different tools I haven't used - Gainsight, Salesforce, Vitally, ClientSuccess, etc. Should I still apply if I haven't used their specific tech stack?”

A: This is a common worry I hear from CSMs, but let me help you see this differently. Think about when you're onboarding a new customer - they might be worried about learning your product, but you know that understanding core concepts matters more than specific button clicks.

The same principle applies to CS tools. Most customer success platforms solve similar problems - they help you track customer health, manage communications, monitor usage data, and automate workflows. If you've used any CS platform effectively, you can learn another one. What matters more is how you think about using technology to solve customer challenges.

Let me share a concrete example. I worked with a CSM who had only used Vitally but wanted to apply for roles requiring Gainsight experience. Instead of focusing on the specific tool, we highlighted how she approached using technology to scale customer success. Her story went something like this:

"In my current role, I noticed our team was struggling to track customer health consistently. Using Vitally, I built a comprehensive health scoring system that combined product usage data, support tickets, and engagement metrics. The underlying logic was what mattered - understanding which signals predict customer success and how to weigh them effectively. The result was catching at-risk customers 60% earlier and improving our team's efficiency by 40%. While I haven't used Gainsight specifically, I understand the principles of building effective customer health monitoring systems and can apply that knowledge to any platform."

This approach worked because it showed:

1. She understood the fundamental problems CS platforms solve

2. She could think systematically about using technology

3. She had experience building solutions, not just using pre-built ones

4. She could measure and demonstrate impact

Here's how to handle this situation in your applications and interviews:

First, emphasize your experience with similar types of tools. If you've used any customer success platform, CRM, or analytics tool, you understand the basic concepts. Don't just list the tools - explain how you've used them to solve real business problems.

For instance: "While I haven't used ClientSuccess, I've built automated customer health monitoring systems in [your platform] that reduced our response time to risk factors by 50%. I understand the principles of effective health scoring and automated alerting, which translate across platforms."

Second, highlight your track record of learning new technologies quickly. Share examples of other tools you've mastered and how you've used them to drive results. This shows you can adapt to new systems effectively.

Remember, companies aren't really hiring you for your knowledge of specific buttons in their tech stack - they're hiring you for your ability to use technology to make customers successful. Keep applying to roles even if you don't know all their tools. Focus on communicating how you think about using technology strategically to solve customer success challenges.

And don't forget - it's still partly a numbers game. If you're getting good at explaining your technical adaptability this way, maintain a steady volume of applications. Track which types of companies are more open to candidates without specific tool experience. You might find that growth-stage companies care more about your problem-solving ability than your familiarity with specific platforms.

Q: I'm seeing CSM salaries all over the place - from $60K to $160K. How do I know what roles are actually at my level and worth applying to?

A: Let me help you make sense of these wide salary ranges in customer success. The variation isn't random - it reflects important differences in how companies structure their CS organizations and what they expect from their CSMs. Understanding these patterns will help you target the right opportunities.

Think about customer success roles like a pyramid. At the foundation, you have CSMs managing small to mid-sized accounts with straightforward products. As you move up, you find CSMs handling larger portfolios, more complex products, or more strategic responsibilities. Each level typically comes with a corresponding salary range.

Let's break down what drives these salary differences:

First, consider portfolio value. A CSM managing 100 small business accounts worth $500K total will typically earn less than someone managing 10 enterprise accounts worth $5M. This makes sense - the impact of losing or growing an enterprise account is much larger. When you see a role advertising $140K+, they're usually looking for someone who can handle high-value, complex customer relationships.

Company stage also plays a crucial role. Early-stage startups might offer lower base salaries but more equity. Large public companies often offer higher base salaries but less equity upside. For example, a Series B company might offer $85K base with meaningful equity, while a public company might pay $120K base with more modest stock options.

Technical complexity is another major factor. If a role requires deep technical knowledge - like helping customers with complex integrations or working closely with APIs - it will typically pay more than a role focused mainly on relationship management. This is why you might see two CSM roles at the same company with a $30K salary difference.

Here's a practical way to evaluate if a role matches your level:

Look closely at the responsibilities, not just the title. A "Senior CSM" at one company might have similar responsibilities to a regular "CSM" at another. Instead, focus on details like:

• Portfolio size and value

• Expected strategic involvement (like working with C-level contacts)

• Technical requirements

• Team leadership expectations

• Cross-functional collaboration requirements

For example, if you see a role paying $130K that requires leading enterprise implementations, working with technical teams, and influencing product strategy, that's typically targeting CSMs with 5+ years of experience handling complex customers. If you have that background, don't let the high salary deter you from applying.

A common mistake is ruling out roles based solely on salary. Some companies post ranges like "$75K-$140K depending on experience." Many CSMs see that and only focus on the lower number. Instead, look at the full job description. If it matches your experience, apply and let the interview process determine where you fall in that range.

And remember - volume still matters here. Rather than self-selecting out of opportunities, apply to roles where the responsibilities match your experience, regardless of the posted salary range. You might be surprised to find that companies will adjust their range for the right candidate. Track which types of roles and salary ranges lead to interviews - this data will help you fine-tune your targeting.

The goal is to find roles that match your experience level while maximizing your earning potential. Don't limit yourself based on salary numbers alone - focus on finding the right match between your capabilities and the role's requirements.

Q: I keep losing out to candidates from big-name tech companies. How can I compete when I'm coming from a smaller company?

A: Let me help you reframe your experience at a smaller company as a strength rather than a weakness. Many CSMs underestimate just how valuable their experience can be when they've had to work with fewer resources and wear multiple hats.

Think about it this way: At large tech companies, CSMs often have specialized roles with extensive support systems. They might have dedicated onboarding specialists, technical support teams, and established processes for everything. But at smaller companies, you've likely had to build things from scratch, solve complex problems with limited resources, and develop creative solutions on your own.

Let me share a story about a CSM I worked with who faced this exact challenge. She came from a 50-person startup and was competing against candidates from well-known tech companies. Initially, she felt intimidated, but we transformed how she talked about her experience. Instead of saying "I managed customer onboarding," she explained how she built the entire onboarding program from the ground up, reducing time-to-value from 60 days to 30 days with no additional resources.

Here's how to position your smaller company experience effectively:

When discussing your impact, emphasize your breadth of responsibility. For example: "At my current company, I noticed our churn rate increasing. Without a dedicated analytics team, I taught myself SQL to analyze our customer data, identified key risk factors, and built an early warning system that helped us reduce churn by 30%. I then trained our entire CS team on using this system, creating a standardized process for addressing customer risk."

This story shows multiple valuable skills: initiative, problem-solving, technical learning, process creation, and team leadership. At a larger company, this might have involved multiple teams and months of coordination. You solved it independently and got results quickly.

Turn your "limitations" into advantages. Talk about how working with fewer resources taught you to:

1. Be more creative in solving problems

2. Build strong relationships across departments

3. Develop deep product knowledge since you couldn't always escalate to specialists

4. Move quickly and measure results

5. Create scalable solutions with limited budget

For instance: "Because we didn't have a dedicated training team, I created a customer education program using existing tools and content. I recorded key training sessions, built a resource library in our help center, and developed automated email sequences for common questions. This reduced repetitive training calls by 60% while improving customer satisfaction scores."

Remember, many growing companies actually prefer candidates from smaller organizations because they know how to build and scale processes. Someone who's only worked with perfectly polished systems might struggle when things are messier and require more creativity.

When interviewing, listen carefully for the challenges the company is facing. Are they building processes from scratch? Trying to do more with limited resources? Looking to move faster? These are perfect opportunities to share relevant examples from your experience.

Keep applying widely and track which types of companies respond best to your background. You might find that other growth-stage companies particularly value your experience building things from scratch, while larger companies appreciate your ability to work autonomously and create solutions independently.

Your smaller company experience isn't a limitation – it's a demonstration of your ability to drive results with less support and fewer resources. That's incredibly valuable in today's market.

Q: Should I be looking at CSM roles, or am I ready for Senior CSM and Team Lead positions? I don't want to sell myself short.

A: This is a question that trips up even experienced CSMs, so let me help you think through it systematically. The key isn't just about years of experience – it's about understanding how your capabilities align with what companies expect at different levels.

Think about your current work. If you're consistently doing things like building new programs, mentoring other CSMs, or shaping strategy, you might be operating at a senior level already without realizing it. Many CSMs undersell themselves because they're comparing their experience to job titles rather than actual responsibilities.

Let me share an example. I worked with a CSM who had been in the role for four years. She was hesitant to apply for senior positions because she thought she needed more time. But when we dug into her experience, we discovered she had already built her company's enterprise onboarding program, created the health scoring system, and was informally mentoring new team members. She was doing senior-level work – she just wasn't calling it that.

Here's how to evaluate where you truly sit in the CS career ladder:

Look at your strategic impact. Are you just executing established processes, or are you creating new ones? For instance, if you've identified gaps in your customer journey and built solutions to address them – like developing a new QBR framework that increased expansion rates – that's senior-level work.

Consider your sphere of influence. Regular CSMs typically focus on their own portfolio. Senior CSMs often influence the broader organization. If you're regularly collaborating with Product on feature requests, working with Sales to improve handoffs, or helping Marketing create customer stories, you're operating at a senior level.

Think about your autonomy and judgment. When a customer issue arises, do you need to check with others on the approach, or do people come to you for guidance? Senior CSMs aren't just good at handling problems – they're the ones others look to for solutions.

For Team Lead roles, ask yourself:

• Do you naturally take the lead in team projects?

• Are you already helping other CSMs improve their work?

• Can you see beyond individual customer success to team-wide patterns?

• Do you have experience developing processes that others follow?

Here's a practical way to decide what level to target: Look at job descriptions for both regular CSM and Senior CSM roles. Pay attention to the day-to-day responsibilities, not just the years of experience required. You might find you're already doing many of the senior-level tasks.

Remember, you can apply to both levels simultaneously. This isn't about limiting your options – it's about maximizing them. Keep tracking your application and interview results. You might find that different types of companies view your experience differently. A large tech company might see you as a CSM, while a growing startup might value your experience at a senior level.

Don't let perfect be the enemy of good here. If you meet 70% of the requirements for a senior role and have examples of strategic impact, apply. Companies often care more about your ability to think strategically and drive results than whether you've officially held a senior title before.

The goal is to find roles that challenge you and value your full range of capabilities, regardless of the exact title. Focus on finding opportunities where you can make a meaningful impact and continue growing.

Q: Everyone talks about CSM certifications - SuccessHacker, ClientSuccess, RenewedCS, etc. Are they worth investing in during my job search?

A: Let me share a perspective on certifications that might save you both time and money during your job search. The truth is, CS-specific certifications alone rarely make the difference in landing a role. What really matters is your proven ability to drive customer outcomes and business impact.

Think about it from a hiring manager's perspective. They're much more interested in hearing how you improved retention rates or scaled customer programs than seeing a certification on your resume. CS certifications can help you feel more confident in interviews and fill specific knowledge gaps, but they're not usually the factor that gets you hired.

However, there are certain certifications outside of CS that can genuinely help you stand out by adding valuable complementary skills. Let me explain which ones might actually move the needle in your job search:

Project Management Certifications (PMP, CAPM): These can be particularly valuable because enterprise customer success often involves managing complex implementations and cross-functional initiatives. When you can tell an interviewer, "I used my project management training to reduce our enterprise implementation time from 90 to 60 days while maintaining quality," that's powerful.

Technical Certifications: Salesforce Administrator certification, for example, can be extremely valuable because it's such a fundamental platform in CS operations. Many companies use Salesforce heavily, and having deep platform knowledge lets you speak confidently about how you've used it to drive customer success. AWS or Azure certifications can also set you apart, especially for technical CS roles.

Business Analysis Certifications: These can help you tell a stronger story about how you analyze customer data and identify trends. Being able to say, "I combined my business analysis training with CS experience to identify key adoption patterns that predicted churn" shows a deeper analytical approach.

Here's how to think about certification investments during your job search:

If you're considering a CS certification, ask yourself:

• Do I have a specific knowledge gap this would fill?

• Am I losing out on opportunities because I lack formal CS methodology training?

• Would this significantly improve my confidence in interviews?

If the answer is no to these questions, your time and money might be better spent on:

• Building a stronger portfolio of success stories

• Improving how you communicate your impact

• Learning technical skills that are in high demand

• Getting certifications in complementary areas like those mentioned above

Remember, hiring managers are ultimately looking for CSMs who can solve problems and drive results. The best certification is one that helps you do that more effectively, regardless of whether it's specifically focused on CS.

Focus first on being able to clearly articulate your experience and impact. Then, if you decide to pursue certifications, choose ones that genuinely expand your capabilities rather than just add credentials to your resume.

Q: I'm getting mixed messages about whether I should specialize (like enterprise or technical CSM) or stay more general. What's the better career move?

A: Let me help you think through this strategic career decision in a way that considers both market trends and your personal growth. The choice between specializing and staying general isn't just about what jobs are available today – it's about positioning yourself for long-term career growth.

Think about the evolution of customer success as a field. In the early days, most CSMs were generalists by necessity. They handled everything from small businesses to enterprise accounts, from basic product support to technical integrations. But as the field has matured, we're seeing increasing specialization, much like how Sales has evolved to have distinct roles for different segments and needs.

Imagine a CSM who is great at handling technical implementations but also enjoyed the relationship-building aspect of CS. She is torn between pursuing a technical CSM path and staying general. When she analyzed her experience, she found that her ability to bridge technical and business conversations was actually a valuable specialization in itself. She decided to focus on enterprise technical customer success, where she could use both skill sets to help complex customers implement sophisticated solutions.

Understanding market dynamics is crucial here. Companies are increasingly looking for specialized skills in specific areas:

Enterprise CSMs focus on managing complex, high-value accounts with multiple stakeholders and sophisticated needs. These roles typically offer higher compensation but require strong strategic thinking and executive presence.

Technical CSMs concentrate on helping customers with complex implementations, integrations, and advanced feature adoption. These roles are growing in demand as products become more technically sophisticated.

Digital CSMs specialize in managing large numbers of customers through scalable, tech-touch approaches. This is becoming increasingly important as companies look to efficiently serve their small and mid-market segments.

However, being a strong generalist also has distinct advantages. Generalist CSMs often have more career flexibility and can be particularly valuable to growing companies that need versatile team members. They're also well-positioned for leadership roles because they understand all aspects of customer success.

Here's a framework to help you decide:

First, analyze your current strengths and interests. Where do you naturally excel? What parts of your role energize you? If you find yourself volunteering for technical implementations or enjoying strategic conversations with executives, that might indicate where you should focus.

Next, look at your target companies. Different types of organizations value different skills:

• Early-stage startups often need generalists who can handle everything

• Growth-stage companies might want specialists to build out specific capabilities

• Enterprise companies typically have more specialized roles

• Product-led growth companies often seek technical CSMs

Also consider market compensation trends. Certain specializations – particularly enterprise and technical CS – often command higher salaries. But don't let compensation be the only factor. A role you excel in and enjoy will likely lead to better long-term career growth than one you chose purely for money.

Here's my practical advice: Instead of thinking about this as an either/or decision, consider developing a "T-shaped" profile. This means maintaining broad knowledge across customer success while developing deeper expertise in one or two areas. This approach gives you the flexibility of a generalist while offering the advantages of specialization.

For example, you might maintain your general CS skills while developing deeper expertise in enterprise customer success. This lets you take on roles requiring broad CS knowledge while having a specialization that sets you apart.

Remember, this isn't a permanent choice. Many successful CS leaders started as specialists and broadened their expertise over time, while others began as generalists and specialized later based on market opportunities. The key is making a conscious choice based on your strengths and career goals, rather than drifting into either path by default.

Continue applying to roles that interest you across the spectrum while paying attention to what energizes you and where you create the most value. Your experience in the job search process itself – which roles you're drawn to, which interviews feel most natural, which companies show the most interest – will help inform your decision.