Determining if a role is right for you
Landing in the wrong company means more than just daily frustration - it can derail your career growth and force you back into job hunting sooner than you'd like. This guide gives you a systematic approach to researching potential employers, helping you find companies where you can truly thrive as a CSM. The insights you gather will help you ask smarter questions during interviews and identify red flags early.
Part 1: What you can research before interviews
Start your evaluation process with independent research before any interviews. This foundation helps you understand the company's market position and potential red flags, while preparing you to ask more informed questions later.
1. Product analysis
The strength of the product directly impacts your success as a CSM. A great product makes your job significantly easier, while a weak product means constantly fighting uphill battles with customers.
Technical documentation Strong documentation reveals how much a company invests in customer success and proper enablement. Examine their help center, developer docs, and API guides. Look for regular updates, clear implementation instructions, and thorough troubleshooting guides. Poor or outdated documentation often signals deeper problems with customer enablement.
Release patterns The product release history tells you a lot about engineering health and company priorities:
Check the frequency of releases - consistent updates signal good development practices
Review the substance of updates - are they fixing bugs or adding features?
Look for detailed release notes and clear customer communication
Watch for long gaps between releases that might indicate resource problems
Integration capabilities Modern software rarely works in isolation. Understanding the integration ecosystem helps you gauge how well the product works with customers' existing tools:
Review their technology partnerships and integration documentation. Compare the number and quality of native integrations against competitors. Pay special attention to how they handle custom integration requests - this often reveals their flexibility in meeting customer needs.
Platform stability Research how reliably the platform performs for customers. Check if they maintain a public status page showing uptime history. Look for transparency around outages and technical issues. Strong companies typically have clear incident communication processes and take accountability for problems.
Product direction Understanding where the product is heading helps you assess long-term potential. Look for public roadmap information and how they incorporate customer feedback. Strong products usually have active beta programs and clear processes for feature requests. Watch especially for signs that development is slowing or shifting focus away from core customer needs.
When evaluating all these areas, look for patterns over time. Is the product growing stronger or showing signs of neglect? Are they investing in customer-requested improvements or chasing market trends? These patterns help predict your future success potential with the company.
2. Employee signals and sentiment
Understanding how employees - especially other CSMs - view the company provides crucial insights into the real working environment. Here's how to gather and interpret these signals effectively.
Team stability and growth
Start by mapping the CS team's evolution on LinkedIn. This reveals key patterns about company health and CS investment.
Growth patterns Track the CS team's size over time:
Steady growth usually signals strong business performance
Sudden expansion might indicate upcoming challenges with scale
Team shrinkage often reveals problems, especially if accompanied by departures of senior staff
Tenure analysis Look closely at how long CSMs stay with the company. Brief tenures (under 18 months) across multiple team members deserve investigation. Pay special attention to senior CSM and leadership tenure - their stability often indicates team health.
Review analysis
Glassdoor and LinkedIn reviews need careful interpretation. Look beyond the surface ratings to understand the real story.
Review authenticity Watch for these warning signs in company reviews:
Clusters of 5-star reviews using similar language
Vague praise about being "the best place ever"
Reviews mentioning "fast-paced environment for high achievers"
Defensive responses from management to negative reviews
CS-specific insights Focus on reviews from Customer Success teams:
Common complaints about resources or support
Mentions of unrealistic expectations
Comments about cross-functional relationships
Notes about career development opportunities
Leadership signals Pay attention to how employees discuss leadership:
Research the backgrounds of CS leadership specifically. Strong leaders usually have significant CS experience and understand the role's challenges. Be cautious of teams led by executives from sales backgrounds without CS experience - this can signal misalignment on team goals and metrics.
Career progression evidence
Look for concrete signs of internal mobility and growth. Strong companies usually publicize promotions and career development. Search for:
CSMs who have moved into leadership roles
Lateral moves between departments
Creation of specialized roles within CS
Public celebration of team achievements
Remember that employee sentiment provides important context for your evaluation, but it's just one piece of the puzzle. The next section will cover how to analyze customer sentiment and satisfaction signals.
3. Customer sentiment and signals
As a CSM, understanding how customers feel about the product and company is crucial - their experience will soon be your daily reality. Here's how to uncover the real customer experience before you join.
Review analysis
G2, Capterra, and other review platforms offer valuable insights when you know what to look for. Don't just skim the star ratings.
Common themes Look for patterns in customer feedback:
Recurring feature complaints that could signal product gaps - for example, if multiple customers mention reporting limitations or API restrictions, this suggests a fundamental product limitation you'll need to manage
Support and implementation challenges mentioned consistently across different customer sizes and industries - pay special attention if enterprise customers cite poor support, as they often have dedicated resources
Product reliability issues mentioned in reviews over time - watch for patterns of outages or performance problems that could make your job harder
Company responsiveness to customer needs - look for specific examples of how quickly (or slowly) the company addresses customer concerns and feature requests
Response quality Pay attention to how the company handles reviews:
Review their responses to negative feedback. Strong companies acknowledge issues professionally and outline clear solutions. Be wary of defensive responses or generic templates - these often indicate deeper cultural problems with handling customer concerns.
Public customer signals
Case studies and testimonials Look beyond the marketing polish:
Examine implementation timelines in detail - if case studies claim unrealistically fast implementations (like "live in 2 days!"), this could indicate oversimplified marketing that sets wrong expectations
Look for concrete, measurable outcomes rather than vague success claims - strong case studies include specific metrics, ROI calculations, and clear before/after comparisons
Compare results across different customer segments to understand where the product provides the most value - this helps you assess whether their ideal customer profile matches reality
Check if testimonials come from actual product users versus executives who may not use the product daily - user-level feedback often provides more accurate insight into product strengths and weaknesses
Community engagement A strong customer community often indicates product stickiness and customer investment. Research:
Active user groups with regular meetings and strong attendance
Engagement levels in community forums - look for substantive discussions versus basic support questions
Evidence of customer advisory board impact on product decisions
Customer participation and speaking roles at company conferences
Implementation indicators
Understanding the customer onboarding experience helps predict your future challenges.
Timeline analysis Research typical implementation periods:
Compare stated timelines in marketing materials against actual customer reports in reviews and social media
Look for mentions of specific challenges that caused delays, especially around data migration or integration
Note how implementation complexity scales with customer size - if enterprise implementations consistently run long, this indicates complexity you'll need to manage
Check what resources customers need to provide - heavy technical requirements could signal implementation challenges
4. Market position and competition
Understanding where a company stands in their market helps you assess both job security and future growth potential. Here's how to build a clear picture of their competitive position.
Market presence
Competitor comparison Start with a thorough competitive analysis:
Map out their primary competitors and create a simple feature comparison matrix - this reveals product gaps you'll need to navigate
Look for head-to-head comparison articles from neutral sources like industry analysts or tech review sites
Watch for patterns in competitor positioning - if multiple competitors point out the same weaknesses, these are likely real issues you'll face
Track which companies they win against and lose against in competitive deals (look for hints in G2 reviews where customers mention switching from or to competitors)
Industry recognition Look beyond marketing claims:
Search for independent analyst coverage from firms like Gartner or Forrester - look specifically at where they place in industry quadrants or waves
Check for industry awards that matter - focus on awards from respected organizations rather than pay-to-play recognitions
Review conference speaking slots and topics - companies leading their markets usually have prominent speaking positions
Look for thought leadership content that shows deep industry expertise versus generic marketing material
Growth indicators
Market expansion Track how they're growing:
Follow their geographic expansion - new office locations or market launches can indicate healthy growth but also potential growing pains
Watch for new product launches and acquisitions - these show innovation but can also create integration challenges
Monitor customer segment expansion - moving upmarket or downmarket often signals strategy shifts that affect CS
Note any shifts in target industry focus - rapid shifts might indicate trouble in their core market
Investment patterns Research where they're putting resources:
Track hiring patterns across departments - heavy investment in CS and product typically signals customer-centric growth
Look for news about new partnerships or strategic alliances that expand their market reach
Watch for infrastructure investments like new data centers or security certifications
Note any recent leadership hires and their backgrounds - this often reveals strategic priorities
Competitive positioning
Market messaging Analyze how they position themselves:
Review their messaging evolution over time through website archives and press releases. Watch for significant shifts in positioning - steady refinement is healthy, but dramatic changes might indicate market fit issues or strategic confusion that could affect your role.
Pricing transparency Understanding their pricing approach reveals a lot:
Check if pricing is public or hidden - lack of transparency often indicates complex sales cycles
Compare pricing models with competitors - significant differences might signal market pressure
Look for recent pricing changes - frequent changes could indicate market challenges
Research discounting patterns mentioned in reviews or earnings calls
Remember: your success as a CSM partly depends on having a strong product in a good market position. Use these insights to evaluate whether the company has sustainable advantages or concerning weaknesses.
5. Financial health and stability
Understanding a company's financial health helps predict job security and growth potential. While private companies won't share everything, there are many signals you can analyze.
Funding analysis
After that, look beyond just the total funding amount:
Track the time between funding rounds - gaps over 24 months without clear profitability could signal fundraising challenges
Research investor quality - top-tier VCs often indicate stronger due diligence and better growth prospects
Watch for down rounds or flat rounds where valuation doesn't increase - these often indicate performance concerns
Note any bridge rounds or convertible notes - these can signal cash flow problems if not part of a clear growth strategy
Growth and burn rate Search for signs of sustainable growth:
Even without exact numbers, you can spot patterns. Watch employee count over time, office expansions or contractions, and public investments in infrastructure. Rapid hiring followed by layoffs often indicates poor cash management or market challenges.
Revenue indicators
For private companies, piece together the revenue picture from available signals:
Growth signals
Track customer logos over time - are they adding major brands or losing them?
Monitor job openings across departments - healthy companies typically maintain steady hiring
Watch for expansion into new markets or product lines - this usually indicates strong core business performance
Note partnership announcements with major platforms or resellers
Warning signs to watch for Look for concerning patterns:
Sudden office closures or lease terminations
Multiple executive departures in short periods
Reduced sponsorship of industry events
Scaling back perks or benefits
Delayed vendor payments (check Glassdoor reviews for mentions)
Market validation
Industry confidence Research how the broader market views the company:
Look for partnerships with established companies - strong partners usually indicate solid due diligence
Check if major customers are expanding their usage publicly
Watch for positive coverage from industry analysts
Monitor their ability to attract and retain senior talent
Competitive responses Analyze how competitors view them:
Do competitors mention them in earnings calls or press releases?
Are they included in competitive comparison guides?
Do enterprise customers consider them seriously in RFPs?
Are they winning significant deals against established players?
Public company indicators
If they're public or planning to go public:
Review SEC filings for revenue growth, margins, and cash flow trends
Study earnings call transcripts for customer metrics and strategy shifts
Watch institutional investor ownership patterns
Monitor insider stock transactions
Remember: financial stability directly impacts your job security and growth opportunities. Use these indicators to assess risk levels and growth potential before committing to a role.
6. Technical foundation and tools
As a CSM, you need to understand enough about the company's technical setup to explain it to customers and anticipate potential challenges. Here's what to look for:
Product reliability
System stability Check how reliable the product is:
Search reviews specifically mentioning system reliability. Pay attention when enterprise customers mention downtime, as they often have strict uptime requirements
Watch for patterns in technical problems - occasional issues are normal, but frequent mentions of the same problems suggest deeper issues
Look at how they communicate during outages - transparent, detailed updates show respect for customers, while vague or delayed communication can make your job harder
Customer experience Research how easy the product is to use:
Check if customers frequently mention needing developers or technical experts to use basic features - this often means you'll spend more time handling technical questions
Look for reviews mentioning the admin experience - if customers say the admin interface is confusing, you'll likely spend lots of time on basic support
Study implementation timelines mentioned in reviews and case studies - if customers consistently say implementations take longer than the company claims, this will affect your onboarding success
Read how customers describe the support experience - look for mentions of response times and whether technical issues get resolved quickly
Integration and data
Working with other tools Understand how well it plays with other software:
Map out their key integrations - for example, if you're selling to sales teams but don't integrate with Salesforce, that's a major limitation you'll have to explain constantly
Look for customer complaints about missing connections to essential tools in their industry - these gaps will become your daily challenges
Check if customers need developers to set up basic integrations - this can significantly slow down implementation and time to value
Research their marketplace or integration directory - a healthy ecosystem of pre-built integrations usually means easier implementations
Data handling Learn how they manage customer data:
Look up their security certifications (like SOC 2) on their security or compliance page - missing essential certifications will limit your enterprise deals
Research any security incidents in their history - check their response and what they did to prevent future issues
See if customers mention concerns about data exports or migrations - if it's hard for customers to get their data in or out, this creates friction
Check if they offer different data storage locations for international customers - this matters for global companies with data residency requirements
Remember: You don't need to be a technical expert, but understanding these basics helps you identify potential roadblocks before they become problems with your customers.
7. Leadership and company values
Understanding leadership's vision and values helps predict your daily work environment and long-term success potential. Here's how to assess the company's leadership approach.
Executive team assessment
Leadership background Research the executive team thoroughly:
Study the backgrounds of key leaders, especially the CEO and CS leadership. Watch for leaders with hands-on CS experience versus those from pure sales backgrounds. Sales-driven leadership often struggles to balance customer success with revenue goals
Track executive tenure and turnover patterns. If multiple executives have left within a short period, especially in CS roles, this could indicate internal problems or lack of CS investment
Review their public content like blog posts, conference talks, and interviews. Leaders who consistently talk about customer outcomes and CS strategy, rather than just revenue and growth, typically build more CS-friendly cultures
Look up their previous companies and roles. Leaders who have successfully scaled CS organizations before are more likely to understand what you need to succeed
Customer success positioning Evaluate how leadership views CS:
Check where CS sits in the org chart. CS should ideally report directly to the CEO or COO. If CS reports through Sales, watch for signs that customer success metrics are balanced with sales targets
Research how often CS leaders speak at company events or write thought leadership content. Active CS voices in company messaging usually indicates CS has real influence
Watch for mentions of CS in company announcements and updates. Are they just talking about retention numbers, or do they highlight customer outcomes and CS team achievements?
Decision making culture
Communication style Look for evidence of how decisions are made:
Study how they announce and explain major changes. Good leaders share clear rationale and show they've considered impact on customers and CS teams
Check their response style to public criticism on review sites or social media. Do they get defensive, or do they engage constructively and show willingness to improve?
Look for regular company updates about strategy and direction. Consistent, transparent communication helps CS teams align with company goals
Customer focus Assess their commitment to customers:
Review their product roadmap and update process. Companies truly focused on customers usually have clear, public roadmaps and regular progress updates
Look for examples where they've changed direction based on customer feedback. Strong companies share these stories openly, showing they value customer input
Watch for signs of prioritizing quick wins over customer outcomes. Check if they rush out features without proper testing or support documentation
Remember: Leadership sets the tone for how CS is valued and supported. Their approach directly impacts your ability to serve customers effectively.
Part 2: What to investigate during interviews
While external research is valuable, interviews provide crucial insights you can't find online. The key is asking the right questions and reading between the lines of the answers you receive.
1. Customer success operations
When you interview for a CS role, it's easy to focus on the basics like salary and benefits. But understanding how the CS team actually operates day-to-day is crucial for your success and happiness in the role. Poor operations can make even the best products and highest salaries frustrating.
The way a company runs its CS team tells you a lot about how much they value customer success. Strong operations show they're serious about helping customers and supporting their CS team. Weak operations often mean you'll spend more time fighting internal problems than helping customers succeed.
Team structure and support
Ask detailed questions about reporting structure:
"Can you walk me through how the CS team is organized?" Listen for clarity and consistency across different interviewers. If they can't explain it clearly, this often signals internal confusion
"How does CS collaborate with Product and Engineering?" Watch for signs of healthy partnerships versus adversarial relationships
"Who do CSMs escalate to when they need support?" Vague answers about escalation paths often indicate poor internal processes
Red flags:
Different interviewers giving conflicting answers about structure
Hesitation when discussing cross-functional relationships
Responses like "we're figuring that out" or "that's evolving" without clear plans
No clear escalation path for urgent issues
Lack of structured collaboration with other departments
Workload and capacity
Dig into the reality of account loads:
"What's the typical book of business for a CSM?" Don't just accept the number - follow up with "How did you determine that was the right number?"
"Walk me through a typical week for a CSM." Listen for signs of realistic scheduling versus constant firefighting
"How do you handle coverage during vacation or sick time?" This reveals if they're understaffed
Red flags:
Unrealistic account loads without clear justification
No system for coverage during time off
Signs of regular overtime or weekend work
Constant reactive mode versus strategic work
High turnover due to burnout
Tools and processes
Ask about their CS tech stack:
"What tools do CSMs use daily?" Watch for signs of proper tooling versus manual workarounds
"How do you track customer health and success metrics?" Lack of clear metrics or proper tools is a major red flag
"What's your process for documenting customer interactions?" Listen for structured approaches versus "everyone does it their way"
Red flags:
Heavy reliance on spreadsheets for critical processes
No dedicated CS platform or customer health scoring
Mentions of "building our own tools" without clear timelines
Poor integration between systems
Inconsistent documentation practices
Process maturity
Investigate how developed their CS operation is:
"Could you share an example of a recently improved CS process?" This reveals if they're actively optimizing operations
"How do you handle customer QBRs?" Look for standardized approaches versus ad-hoc processes
"What does your customer onboarding process look like?" Listen for well-defined stages versus loose guidelines
Red flags:
No standardized processes for key activities
Lack of continuous improvement mindset
Individual CSMs creating their own approaches
No clear metrics for process success
Poor or outdated documentation
2. Customer portfolio and segmentation
The customers you work with daily will make or break your experience as a CSM. Even great companies can be a poor fit if their customer base doesn't match your skills and interests. Many CSMs learn this the hard way - discovering too late that they're supporting customers they're not equipped to help or interested in working with.
Before taking a role, you need to understand:
What types of customers you'll support
How healthy the customer base really is
How your success will be measured
What role you'll play in growing accounts
Good companies have clear answers about their customers and aren't afraid to discuss challenges. If a company paints a perfect picture with no problems, that's usually a warning sign - every customer base has its complications.
This section shows you exactly what to ask to uncover the real customer landscape. The questions and red flags here come from experienced CSMs who learned to spot the difference between healthy customer portfolios and problematic ones.
Portfolio composition
Ask detailed questions about your potential customers:
"Could you break down a typical CSM portfolio by industry and company size?" Listen for alignment with your experience and interest areas
"How do you segment customers, and how does that affect CSM workload?" Watch for logical segmentation versus random assignment
"What's the mix between technical and non-technical customers?" This reveals the expertise you'll need daily
Red flags:
No clear segmentation strategy in place
Portfolios that mix enterprise and SMB customers without logic
Constant portfolio reshuffling without strategic reasons
More than 3-4 different industries per CSM
Unwillingness to share specific numbers about account load
Customer health
Dig into the real state of accounts:
"What percentage of your customers are considered healthy versus at-risk?" Watch for honesty about challenges
"Walk me through how you handled a recently churned customer." Their approach to failures reveals company maturity
"What's your current logo retention rate?" Listen for specific numbers and trends
"How do you define and measure customer health?" Look for sophisticated metrics beyond just renewal status
Red flags:
Unwillingness to discuss retention metrics
Blaming customers for all churn instances
No clear definition of customer health
Retention rates significantly below industry standards
No systematic way to identify at-risk customers
Success metrics
Get specific about how you'll be measured:
"What are the key metrics CSMs are evaluated on?" Watch for balanced metrics versus pure revenue focus
"How do you measure customer health beyond renewal rates?" Look for sophisticated understanding of customer success
"What does a successful first year look like for a CSM?" Listen for realistic expectations versus impossible targets
"How often are these metrics reviewed and adjusted?" This reveals flexibility and realism in goal-setting
Red flags:
Pure focus on revenue without customer health metrics
Unrealistic targets (like 100% retention expectations)
Metrics that conflict with each other
No clear onboarding success metrics
Frequent changes to success metrics without clear reasoning
Growth responsibility
Understand your role in expansion:
"How do CSMs and Sales work together on expansion opportunities?" Watch for clear process versus constant conflict
"What percentage of a CSM's time is expected to focus on growth?" Listen for realistic balance
"How are expansion wins credited between Sales and CS?" Look for fair partnership approaches
"What resources are available to support expansion efforts?" This reveals if you'll have proper tools and support
Red flags:
No clear distinction between CS and Sales responsibilities
Expansion targets without dedicated resources
History of conflict between CS and Sales over accounts
Commission structures that encourage wrong behaviors
Lack of process for handling expansion opportunities
Remember: Strong companies have clear, realistic expectations and aren't afraid to discuss challenges. If everything sounds too perfect, keep digging - no customer portfolio is without its complications.
3. Role specifics and expectations
Many CSMs start new jobs only to discover the role is very different from what they expected. The job description might look great on paper, but the daily reality can be another story. Getting clear about expectations upfront helps you avoid unpleasant surprises and sets you up for success.
You need straight answers about:
What you'll actually do day-to-day
How work-life balance really works
Travel and location requirements
How you'll be paid and rewarded
Smart CSMs dig deep into these areas during interviews. It's much better to uncover mismatched expectations before taking the job than to discover them after you've started.
This section gives you specific questions to ask about the role and shows you what to watch out for in the answers. We'll help you spot the difference between companies that have clear, reasonable expectations and those that might demand more than they're telling you.
Core responsibilities
Key questions to ask:
"What are the top 3 priorities for a CSM in their first 90 days?" Listen for clear expectations versus vague goals
"What does success look like in this role at 6 months and 1 year?" Watch for realistic timelines and clear metrics
"How is a CSM's time typically split between different activities?" Look for balanced workload versus constant firefighting
Red flags:
Unclear or constantly changing priorities
Unrealistic expectations for ramp-up time
No structured onboarding plan
Excessive time spent on non-CS activities
Conflicting success metrics
Work-life balance
Key questions to ask:
"What are the expectations around working hours and availability?" Listen for reasonable boundaries
"How does the team handle after-hours customer needs?" Watch for structured on-call processes
"What's the typical response time expectation for customer issues?" Look for realistic service levels
Red flags:
Undefined boundaries between work and personal time
Expected 24/7 availability without compensation
Regular weekend work requirements
No clear on-call rotation
Different rules for different team members
Travel and location
Key questions to ask:
"What's the travel expectation for this role?" Get specific percentages and frequencies
"How flexible is the company about remote work?" Watch for established policies versus case-by-case decisions
"How does the team handle different time zones?" Look for reasonable accommodation
Red flags:
Unclear travel expectations
Frequent last-minute travel requirements
Poor travel expense policies
Inconsistent remote work rules
Unrealistic time zone coverage expectations
Compensation structure
Key questions to ask:
"How is the compensation package structured?" Look for clear breakdown of base, bonus, and any commission
"What metrics drive variable compensation?" Watch for achievable versus stretch targets
"How often are compensation and performance reviewed?" Listen for regular, structured reviews
Red flags:
Vague answers about bonus calculations
Unrealistic targets for variable pay
Frequent changes to compensation structure
No clear path for compensation growth
Different rules for similar roles
4. Team dynamics
The daily experience of working at a company depends heavily on its people and culture. You can have a great product and good pay, but poor team dynamics will make your job much harder than it needs to be. Smart CSMs know that team culture can make or break their success.
You'll spend most of your day working with:
Other CSMs who can help you succeed
Sales teams who hand off new customers
Product teams who shape what you can deliver
Managers who support your growth
This section helps you look beyond the usual "we're like a family" talk to understand how teams really work together. You'll learn what questions to ask about:
How the CS team supports each other
How different departments work together
What kind of management you'll get
How the company handles communication
The questions and red flags here come from CSMs who learned the hard way that culture matters as much as compensation. Use them to spot the difference between healthy team environments and toxic ones.
Team environment
Key questions to ask:
"How often does the CS team meet and what are typical meetings like?" Look for structured collaboration
"What's the mix of experience levels on the team?" Watch for healthy balance of senior and junior CSMs
"How does the team handle knowledge sharing?" Listen for established practices versus siloed knowledge
Red flags:
Lack of regular team interaction
High turnover in the past year
Poor knowledge sharing practices
Competitive rather than collaborative environment
Siloed information and resources
Cross-functional collaboration
Key questions to ask:
"How does CS work with Sales on handoffs and expansions?" Watch for clear processes
"What's the relationship like between CS and Product?" Listen for genuine partnership versus friction
"How are conflicts between departments typically resolved?" Look for mature resolution processes
Red flags:
Tension between CS and Sales
No regular interaction with Product team
Unclear handoff processes
History of inter-department conflicts
CS team treated as "cleanup crew"
Management style
Key questions to ask:
"How often do CSMs meet with their manager?" Listen for regular, structured support
"What's the management team's approach to professional development?" Watch for investment in growth
"How does the team handle performance challenges?" Look for supportive versus punitive approaches
Red flags:
Infrequent or cancelled 1:1s
Micromanagement tendencies
Lack of feedback and coaching
Poor handling of team conflicts
No investment in team development
Communication practices
Key questions to ask:
"How does leadership communicate company updates to the team?" Look for transparency
"What channels do CSMs use to raise concerns or suggestions?" Watch for open feedback culture
"How are CS team wins and learnings shared?" Listen for celebration of success
Red flags:
Poor communication from leadership
No clear channels for feedback
Lack of transparency about challenges
Fear of raising issues
No recognition of team achievements
5. Broader Culture
Before joining any company, you need to understand more than just your team and role. The company's overall culture will shape everything from strategic decisions to daily operations. Smart CSMs know that misalignment at this level can make even great roles unsustainable.
You need to understand:
If leadership's priorities match their public statements
How the company approaches change and innovation
What the company truly values when making tough decisions
How transparent they are about challenges and direction
Whether their mission actually guides decisions
Mission and values alignment
Key questions to ask:
"How have recent company decisions reflected the stated mission?"
"When revenue and values conflict, how does the company decide?"
"Can you share a time when the company lost money to stick to its values?"
"How do company values influence product and pricing decisions?"
Red flags:
Can't provide examples of values guiding decisions
History of compromising values for short-term gains
Defensive responses about past decisions
Different rules for big versus small customers
Mission statement contradicts actual behavior
Leadership approach
Key questions to ask:
"How does executive leadership communicate difficult news?"
"What access do employees have to senior leaders?"
"How does leadership handle employee pushback on decisions?"
"What's the biggest mistake leadership has admitted to recently?"
Red flags:
Leaders who are never wrong
Poor communication during challenges
History of surprising employees with major changes
Different messages to different audiences
Blame-shifting when things go wrong
Innovation and change
Key questions to ask:
"How does the company approach major change initiatives?"
"What's the biggest risk the company has taken recently?"
"How does the company gather and act on employee ideas?"
"What's the balance between stability and innovation?"
Red flags:
Constant reactive changes
No clear innovation process
History of failed transformations
Risk-averse to the point of stagnation
Innovation limited to certain groups
Financial transparency
Key questions to ask:
"How does the company communicate its financial health?"
"What metrics does leadership share with employees?"
"How are resource allocation decisions explained?"
"What's the company's approach to sustainable growth?"
Red flags:
Unwillingness to discuss finances
Sudden cost-cutting without context
History of unstable funding
Unclear business model
Growth at all costs mentality
Company resilience
Key questions to ask:
"How did the company handle its last major challenge?"
"What's the company's approach to industry changes?"
"How does the company prepare for economic uncertainty?"
"What's the backup plan if current strategies don't work?"
Red flags:
No clear contingency plans
History of layoffs without warning
Poor handling of past crises
Unwillingness to discuss challenges
Overconfidence in current approach
Remember: Strong companies have cultures that balance optimism with realism and can explain their choices clearly. If you hear vague answers about company-wide practices or see misalignment between words and actions, those are serious warning signs about the broader culture.
6. Risk assessment and challenges
Every company faces challenges, and good ones are honest about them. If a company claims everything is perfect, they're either hiding problems or out of touch with reality. Smart CSMs know it's better to understand the challenges upfront than discover them after taking the job.
You need to know:
What problems the team is dealing with now
How well they compete in their market
What support you'll have when things get tough
Where the company is really heading
This section helps you dig past the recruiting pitch to understand the real challenges you'll face. Companies that are open about their problems and have clear plans to address them are usually healthier than those that pretend everything is perfect.
The questions here help you spot the difference between:
Normal growing pains versus serious problems
Healthy competition versus market struggles
Good support systems versus being left on your own
Real growth plans versus wishful thinking
Use these questions to understand what you're really walking into. Every job has challenges - the key is making sure they're challenges you're prepared to handle.
Current challenges
Key questions to ask:
"What are the biggest challenges facing the CS team right now?" Watch for honesty versus sugar-coating
"How is the company preparing for potential economic downturns?" Listen for realistic contingency plans
"What are the main reasons customers churn?" Look for systematic understanding versus excuses
Red flags:
Unwillingness to discuss challenges
No clear plan for handling market changes
Blaming customers for all problems
History of layoffs without clear communication
Frequent restructuring
Market position
Key questions to ask:
"What consistent challenges do you face against competitors?" Watch for honest assessment
"How does your product roadmap address competitive gaps?" Listen for realistic plans
"What's your win/loss rate in competitive deals?" Look for transparency about market position
Red flags:
Dismissive attitude toward competition
Inability to articulate competitive advantage
Frequent loss of customers to competitors
No clear product differentiation
Unrealistic view of market position
Support structure
Key questions to ask:
"What resources are available when CSMs need help?" Watch for established support systems
"How does the company handle unexpected customer challenges?" Listen for systematic approaches
"What happens when a CSM gets overloaded?" Look for realistic backup plans
Red flags:
No clear escalation paths
Limited technical support resources
Poor crisis management history
Understaffed support teams
Reactive versus proactive planning
Future outlook
Key questions to ask:
"What are the growth plans for the CS team?" Watch for realistic scaling plans
"How does CS fit into the company's long-term strategy?" Listen for strategic versus tactical role
"What major changes are planned for the next year?" Look for transparent communication
Red flags:
Unclear growth strategy
Unrealistic hiring plans
History of failed initiatives
Poor change management
Lack of long-term vision for CS
FAQs
Q: What are the most telling signs of a company's financial health when researching a potential employer?
A: Even with private companies that don't share detailed financials, you can piece together their financial health through several key indicators:
Start by analyzing their funding history. Watch for concerning patterns like gaps over 24 months between funding rounds without clear profitability, down rounds where valuation doesn't increase, or bridge rounds that might signal cash flow problems. The quality of their investors matters too - top-tier VCs often indicate stronger due diligence.
Look for growth signals in their public presence. Track customer logos over time - are they adding major brands or losing them? Monitor job openings across departments, as healthy companies typically maintain steady hiring. Watch for expansion into new markets or product lines, which usually indicates strong core business performance.
Pay attention to warning signs like sudden office closures, multiple executive departures in short periods, reduced presence at industry events, scaling back of perks, or delayed vendor payments (often mentioned in Glassdoor reviews).
Study market validation through partnerships with established companies, which usually indicate solid due diligence. Watch if major customers are publicly expanding their usage and if the company is winning significant deals against established players.
If they're public, review SEC filings for revenue growth, margins, and cash flow trends. Study earnings call transcripts for customer metrics and monitor insider stock transactions.
Q: What should I ask in interviews to understand what working on the CS team is really like?
A: During interviews, ask clear questions that show you the day-to-day reality of the job: Ask about the team setup: "Who do CSMs work with daily? Who do they go to when they need help?" Listen carefully if different interviewers give different answers - this usually means there's confusion about how things work.
Find out about workload: "How many accounts would I handle? How did you pick this number?" Ask them to describe what a normal week looks like for a CSM. If they talk about constant emergencies or working weekends, that's a warning sign.
Learn about their tools: "What software do CSMs use every day? How do you track if customers are doing well?" Be careful if they say they mostly use spreadsheets or are "working on building better tools" - this usually means they lack proper systems.
Check their processes: "Can you walk me through how you handle customer onboarding?" Listen for clear, standard ways of doing things versus "everyone does it their own way.
Q: What signs show that a company really values its Customer Success team?
A: Look for these clear signs that a company takes CS seriously: Look at who CS reports to. If CS reports directly to the CEO or COO, that's good. If CS reports to Sales, watch out - this often means they care more about sales targets than customer success.
Check how they make decisions about product changes. Good companies regularly ask CS teams for input and actually use it. If CS isn't involved in product decisions, you'll likely struggle to help customers with product problems.
Look at their team support. Strong companies have clear backup plans when CSMs are sick or on vacation. They also have proper tools for tracking customer health and sharing information. If they expect CSMs to handle everything alone or use messy spreadsheets, that's a bad sign.
Pay attention to how they talk about problems. Good companies are open about challenges and have clear plans to fix them. If they blame customers for all problems or avoid talking about issues, that's a red flag.
Check their growth plans for CS. Ask about training, promotion paths, and plans to grow the team. If they can't explain how CSMs can advance or learn new skills, they probably don't invest much in their CS team.
Q: How can I tell if the customer portfolio I'd be managing is a good fit?
A: Ask these specific questions to understand who you'll be working with:
"What types of customers would I handle?" Get clear about their size, industry, and technical skills. If you'd be juggling very different types of customers (like big enterprises mixed with small businesses), that could mean trouble.
"How many customers would I manage?" Get a real number, not just a range. Then ask how they decided on that number. If they can't explain why it's reasonable, or if it seems too high, be careful.
"What does a healthy customer look like?" Good companies can clearly explain what makes customers successful. They should share specific examples and numbers, not just talk about renewal rates.
"What makes customers leave?" Listen for honest answers about why customers quit. If they only blame customers or avoid the question, that's a warning sign. Good companies understand and learn from customer losses.
"How do you match CSMs with customers?" There should be a clear plan for this, not just random assignment. Make sure the customers you'd work with match your experience and interests.
Q: What should I look for in the company's product before taking a CS job?
A: Look at these key things that will affect your daily work:
Check if the product actually works well. Look at their status page to see how often it has problems. Read customer reviews about reliability. If customers often mention crashes or slowness, you'll spend a lot of time dealing with angry customers.
See how hard it is to use. If customers constantly need technical help for basic tasks, that means you'll spend most of your time answering simple questions instead of helping customers succeed. Look at how it connects with other tools. If it doesn't work well with common software your customers use (like Salesforce for sales teams), you'll have a hard time getting customers to use it regularly.
Check their product updates. Look for regular improvements and bug fixes. If they rarely update the product or take forever to fix problems, customers will get frustrated and blame you.
Read their help documents. Clear, updated help guides make your job much easier. Poor documentation means you'll spend lots of time explaining basic things that should be written down.
Q: What are the biggest red flags I should watch for when researching a company?
A: Watch out for these clear warning signs:
Lots of CSMs leaving within their first year
Different interviewers giving conflicting answers about how things work
No clear way to handle urgent customer problems
CSMs regularly working nights and weekends
Poor relationships between CS and other teams
Heavy focus on sales without caring about customer success
Blaming customers for all problems
Using basic spreadsheets instead of proper CS tools
No clear plan for helping CSMs grow in their careers
Unrealistic expectations (like managing too many accounts)
Q: How can I organize all this research to make a good decision?
A: Create a simple checklist that covers:
Product health: How reliable is it? How often do they improve it?
Customer signs: Are customers generally happy? What makes them leave?
Team setup: How is CS organized? What tools and support do they have?
Work reality: How many accounts? What's a typical day like?
Growth potential: Can you advance? Do they invest in training?
Company health: Are they growing? Do they have enough money?
Rate each area as Good, Okay, or Worried based on what you find. If you're "Worried" about more than one or two areas, that's usually a sign to keep looking. Trust your research - if several things feel off, they probably are.
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