Start here if you've lost your job or been laid off
The first days after leaving a CSM role can feel overwhelming. This guide focuses on your immediate needs and next steps. For longer-term career planning and job searching, refer to our other dedicated guides.
Immediate response cheat sheet
Take these immediate steps to stabilize your situation and protect your interests in the first 48 hours:
Gather critical documents immediately
Forward every important email to your personal account before you lose access. Think: accomplishments, kudos from customers, project successes.
Download your last few performance reviews. These are helpful for interviews and negotiations later.
Save any training certificates. Especially if they're for tools like Salesforce or Gainsight that you might use elsewhere.
Keep those great customer testimonials, but be smart about confidentiality. Remove identifying details if needed.
Back up your work portfolio, but be careful. Don't take proprietary stuff. Focus on public-facing materials and your own created content.
Make folders like "Performance Docs," "Training/Certs," "Customer Success Stories," and "Project Results" - you'll thank yourself later.
Create your documentation workspace
The next few weeks will be a blur of deadlines, paperwork, and important conversations. Missing details now could cost you benefits or opportunities later. Here's how to capture everything:
Open up a fresh Google Doc or grab a notebook - whatever works for you. You need one central place to track everything. This prevents crucial information from getting lost in scattered notes or email threads.
Write down everything about your departure conversation while it's fresh - who said what, what was promised, key dates, everything. Your memory of these details will fade quickly, and you might need this information later for severance negotiations or if there are any disputes about terms.
Create simple sections: "Need to handle NOW" (next 2 days), "Need to handle THIS WEEK" (next 7 days), and "Can handle LATER" (everything else). This helps you focus on urgent priorities without losing track of important but less time-sensitive tasks.
Include a running list of questions as they pop up - you'll probably think of new ones hourly at first. Having these documented means you can address them efficiently in conversations with HR or your manager, rather than remembering them after the fact.
Handle immediate access and security
Make a list of every single work tool you're logged into. Everything from Slack to that random project management tool you used once.
Figure out which systems have customer data or company info you need to properly hand off.
Export your contacts but be careful. Don't take customer contact info unless you're absolutely sure it's allowed.
Go through your phone and laptop. Remove your work email and any other company apps.
Save bookmarks for useful industry resources and tools before you lose access to your work browser.
If you used your work email to sign up for any personal accounts (we all do it), change those over to your personal email now.
Take a full 24 to 48 hour pause before making any public moves
I know you want to jump into action, but trust me. Take at least 24 hours to process. Your emotions are running high right now, and you might regret hasty decisions. This isn't the time to blast social media or make big announcements. Use this pause to clear your head and make a solid plan instead of reacting emotionally.
Take time to acknowledge your feelings about this transition. Job losses can bring up complex emotions - from betrayal to shame to anger. These feelings are normal and valid
Remember that workplace situations leading to departures are often complicated and not a reflection of your worth or capabilities
Consider talking with a trusted friend or counselor to process these emotions before crafting your public messages. Clear communication comes from a clearer headspace
Give yourself permission to feel frustrated or hurt, but try to keep those emotions separate from your professional communications
If you do decide to make the announcement, go ahead and turn off your social notifications. You don't need the distraction of LinkedIn connection requests and "sorry to hear" messages right now.
If recruiters or companies reach out (and they probably will), just send a quick "Thanks for thinking of me. I'm taking a few days to organize my transition, and I'll get back to you next week".
Take care of your emotional wellbeing
Your nervous system is probably in overdrive right now, and that can lead to impulsive decisions or catastrophic thinking. Here's how to stay grounded:
Physical regulation basics:
Start with basic physical regulation. Take a walk outside, do some deep breathing exercises, or put on music that helps you feel calm. Your body needs to settle before your mind can follow.
Choose activities that keep you present and grounded. This might be gardening, cooking, exercise, or whatever typically helps you decompress in stressful times.
Maintain your regular eating and sleeping schedule as much as possible. Your body needs this stability right now.
Managing your thoughts and emotions:
Set up specific times to connect with supportive people who will listen without jumping into problem-solving mode. Let them know if you just need to vent.
Give yourself permission to feel whatever comes up, but try to postpone any big decisions until you're feeling more settled.
If you notice yourself spiraling into worst-case scenarios, redirect your focus to concrete tasks from your documentation list.
Creating structure:
Schedule designated worry time - 30 minutes where you can stress, then try to park those thoughts outside that window.
Keep your routine as normal as possible - regular meals, sleep schedule, and daily structure will help you feel more stable.
Break your day into smaller chunks with specific tasks. This helps prevent feeling overwhelmed by everything at once.
Start your financial snapshot
Open a spreadsheet and be brutally honest about your numbers. Exactly how much savings you have accessible right now.
List out every payment you're expecting: final paycheck, PTO payout, expense reimbursements, commissions, bonus, severance.
Pull up all your bills and subscriptions. What's due in the next 30 days and what can wait.
Check your healthcare card. Write down exactly when your coverage ends and what prescriptions you need to refill.
Look at every company benefit; healthcare, dental, vision, life insurance, disability, 401k. Note which ones need immediate decisions.
Start planning some budget cuts; what subscriptions can go, where can you trim expenses without making yourself miserable.
Build your support system
Pick your trusted advisors carefully - maybe your old mentor, that friend who's great with finances, and someone who's been through this before.
Be specific when you reach out; "Can I bounce some ideas off you about negotiating my severance?" works better than "I need help".
Keep this inner circle small for now. You don't need 20 people giving you conflicting advice.
Consider whether you need a therapist or career coach. This is a lot to process, and professional help can be worth it.
Set up specific check-in times with your support people; "Can we do a quick call Thursday morning?" is better than "Let's talk soon".
Create your action timeline
Map out every deadline on a calendar; when benefits end, when paperwork is due, when you need to return equipment.
Set phone reminders for anything crucial, especially legal or benefits deadlines that can't slip.
Break down your first 48 hours into specific tasks; morning, afternoon, evening.
Make a realistic daily checklist for week one. Focus on the must-dos and save the nice-to-dos for later.
Plan daily 15-minute check-ins with yourself to stay on track, morning coffee works great for this.
Check your state's unemployment website to verify eligibility requirements - having your dates of employment, salary information, and reason for departure ready will speed up the process.
Benefits and logistics
Healthcare continuation
Get clear on your current coverage
Log into your benefits portal and take screenshots of everything. You're looking for: your plan ID numbers, network details, and exactly what's covered. Download your ID cards too - you never know when sites will cut off access. Here's why this matters: Companies sometimes cut off portal access with no warning, and you'll need these details to fight any claims that come up during your coverage gap.
Check your coverage end date in writing. Most companies run till month-end, but get this confirmed. Email HR specifically asking "Can you confirm my health coverage ends on [date]?" This needs to be in writing because verbal confirmations won't help if there's a problem with a medical bill later.
Make a list of any medications you need - then check if you can get 90-day refills before coverage ends. Include medications for any family members on your plan too. Why? Even with COBRA, there can be annoying gaps in pharmacy systems recognizing your coverage. Better to have a buffer of medication than stress about it.
Look at the next 60 days of your calendar. Any doctor appointments scheduled? Write down their office numbers, you might need to reschedule or check about payment options.
If you have FSA/HSA money, check your balance and deadline to use it. Make a quick list of eligible items you actually need (contact lenses, dental work, etc.). This is your money - if you don't use your FSA funds by the deadline, you'll lose them completely. HSA money stays with you, but you might lose access to the particular investment options your employer offered.
Map out your COBRA details
That COBRA packet is coming; it's usually around 20-30 pages and looks scary. Set it aside for now, but don't lose it.
Write down this key fact: You typically have 60 days to decide, and it's retroactive. Here's why this is huge: You can wait to see if you need coverage before paying. If something happens on day 45, you can elect COBRA then and it'll cover you backdated to day 1. This can save you thousands in premiums if you find new coverage quickly.
Do the real math on monthly COBRA costs: Look at your past paystubs. Add your premium + what your employer paid + 2% (this extra 2% is a legally allowed administrative fee to cover the costs of managing your coverage separately from the employer's group plan.) Write down that number. It's usually shocking but important to know. People often assume COBRA will be like their employee contribution - it's not. It's usually 3-4 times higher because your employer isn't subsidizing it anymore.
If you got severance, dig into the details. Sometimes companies pay COBRA for a few months. Find the exact wording about this in your severance agreement. This is often negotiable. If they didn't offer COBRA coverage, you might be able to ask for it
Put three calendar reminders: 30 days (review healthcare needs), 45 days (make initial decision), 58 days (absolute deadline to elect COBRA). Missing these deadlines can leave you without options - and the government won't care that you forgot.
Final compensation details
Document every penny owed to you
Open a new spreadsheet tab called "Money Owed". This is your new best friend. List out: final regular paycheck, PTO hours × your hourly rate, any unpaid expenses (with report numbers), and commission on any closed deals. Why such detail? Companies make mistakes during offboarding all the time. Without your own clear records, you might not catch errors.
Screenshot your last paystub showing PTO balance and hourly rate. Don't trust the exit paperwork to get this right. It's not impossible where HR's numbers are wrong and people lose out on hundreds or thousands in PTO payout.
Grab the commission plan document and any emails about deals in progress. Here's the reality: Commissions often get messy during departures. You need proof of what deals you worked on and what the commission terms were.
Write down any bonuses you hit; retention, performance, quarterly targets. Note the exact targets and your proof of hitting them.
Check your expense reports from the last 60 days and what is still owed to you as reimbursement. Screenshot everything that hasn't been paid yet. Why? Expense reports have a weird way of getting "lost" during transitions.
Track how and when you'll be paid
In your "Money Owed" spreadsheet, create columns for: Amount Expected, Date Promised, Date Received, Payment Method, and Notes.
Forward any emails about payment promises to your personal email with the subject line "Payment Promise - [Type]." Why this specific format? If you need to find these later for unemployment claims or legal issues, you don't want to dig through thousands of emails.
If someone tells you something verbally about payment, send a follow-up email: "Just confirming our conversation that [payment details]". This isn't being paranoid. Verbal promises disappear quickly when management changes or memories fade.
Add calendar alerts 2 days before each expected payment and another on the payment date to check your bank account. Why 2 days before? Because if something's missing, you want to flag it before the weekend when payroll folks might be unreachable.
Keep all pay stubs and payment notifications in a folder called "Final Payments." Here's why: Unemployment often asks for these, and proving commission payments can be especially tricky without documentation.
Company property and access
Create your return inventory
Grab your phone and take photos of all company equipment right now. Get close-ups of any serial numbers and existing wear and tear. This isn't about being difficult, it's protecting you from claims about equipment damage that existed before.
Make a spreadsheet listing: Item, Condition, Serial Number, Date Received, Current Location, Return Deadline. Why so detailed? Because if anything goes missing in transit or there's a dispute later, you need to prove exactly what you had and its condition.
Email HR: "Can you confirm the complete list of items I need to return and the process for returning them?" Save their response. Some companies have tried to charge departing employees for items they didn't even have.
For remote folks: Specifically ask "Will you provide shipping labels or should I expense shipping costs?" Get this in writing. Why? Companies might refuse to reimburse shipping costs because "it wasn't approved", even though they required the returns.
Pack items properly - take photos of packed boxes and shipping labels. Keep all tracking numbers in your spreadsheet. Shipping damage disputes are more common than you'd think, and proof of proper packing can save you hundreds.
Handle digital cleanup
List every work account you have. Start with the obvious (email, Slack) but don't forget random tools you might use once a month (like meeting note takers or project management tools). Why? You need to let your manager know they should close these accounts.
Write down any passwords or bookmarks you need before logging out, especially for industry resources you use regularly. Focus on tools that are public knowledge in the industry, not company-specific resources.
Go through your phone right now and delete work apps but screenshot any important info first (like your calendar). Why? Work accounts can be remotely wiped without warning, taking your contact lists and calendar with them.
Check your Google Drive or Dropbox. Remove work account access but save personal files first. Many people lose personal files because they forget their wedding photos or side project docs were in their work Drive.
Delete work accounts from your browser's autofill and password manager. This matters because if your password manager synced work passwords to personal devices, it could create security risks.
Stock options and equity
Document your current equity situation
Log into your equity platform (like Carta) immediately and screenshot every page showing grants, vesting schedules, and current status. Why? Companies sometimes restrict access quickly, and these details are crucial for tax planning.
Download your complete grant history and all official documentation about your equity. Keep these forever - you might need them years later for tax audits or legal issues.
Create a simple table: Grant Date | Total Shares | Vested Shares | Exercise Price | Exercise Deadline. This isn't just organization - it's about understanding exactly what you own and what you'll lose if you don't act.
Calculate exactly how many shares are vested as of your last day. Include partial vesting if applicable - many people miss out on partially vested shares because they don't realize they're entitled to them.
Write down your post-termination exercise window (the deadline to buy your vested stock options after leaving). Many people lose their vested options because they don't realize that once this deadline passes, their right to buy the shares expires completely. And despite what you might hear, companies rarely extend this deadline.
Financial triage
Immediate expense assessment
Map out your true monthly costs
Pull your last 3 months of bank and credit card statements right now. Why? Most people underestimate their actual monthly spend by 20-30% because they forget irregular expenses.
Create three lists in your spreadsheet:
"Must Pay" (rent/mortgage, utilities, minimum debt payments, insurance).
"Need Soon" (groceries, phone, internet, essential transportation).
"Can Cut" (subscriptions, entertainment, non-essential services) Don't guess at these numbers. Use actual statement data. You need real figures to make survival decisions.
Calculate your real runway
Look at your truly accessible money; checking, savings, any non-retirement investments you could liquidate quickly. Why "truly accessible"? Because retirement accounts often have penalties and tax implications you can't afford right now.
Divide your accessible money by your bare minimum monthly expenses (Must Pay + Need Soon). This is your actual runway in months. Be brutally honest. Optimism about your runway can lead to painful financial decisions later.
Set aside enough for at least 2 months of "Must Pay" items immediately. Even if you get severance or unemployment, payments can be delayed. Having this cushion prevents panic decisions.
Build your survival budget
Calculate the absolute minimum you need monthly to avoid debt or permanent damage (like missing mortgage payments). Some financial hits (like missed mortgage payments) can affect you for years.
List every subscription on autopay; Netflix, Spotify, gym, everything. Don't forget annual subscriptions that might hit during your unemployment. You need to decide now which to keep, pause, or cancel.
Check all your insurance payments; car, life, disability. Some have grace periods, others will cancel immediately for non-payment. Know which is which before you have to choose what to pay.
Emergency income planning
Map out your income sources
Calculate your severance after taxes. This is your first bridge. Why after taxes? Because severance is usually taxed higher than regular pay, and people often get shocked by the actual amount.
Write down unemployment benefit amounts for your state. Google "[Your State] unemployment calculator" and run the numbers. The number might be lower than you expect, but it's guaranteed income.
List any side gigs or contract work you could start immediately. Focus on things you can do without investment or long ramp-up time.
Check your credit card rewards points/miles. Could these cover some expenses while you job hunt? Make a list of what you could convert to cash or necessary expenses.
Look for quick cost reductions
Call your major service providers (phone, internet, insurance) and ask about hardship programs or temporary reductions. Pro tip: Many won't advertise these programs but have them available if you ask directly.
Check your employer benefits for post-employment discounts or services. Some companies offer career transition services, resume help, or even extended benefits you might not know about.
Review any professional subscriptions or memberships. Which ones are truly essential for your job search? Which could you pause and restart later? Remember, some organizations offer unemployment discounts.
Know your backup options
Check credit card interest rates and available credit. Not to use them, but to know your absolute last resort options. It's better to know your options before you're in crisis mode.
Research local emergency assistance programs. Many cities have rent assistance or utility payment programs, but they often have waiting periods. Get on waiting lists now, even if you're not sure you'll need them.
Document any retirement account hardship withdrawal rules. This is a last resort, but know the rules and penalties now. Why? Because these decisions shouldn't be made under pressure - they have long-term implications.
Consider your assets
List anything valuable you could sell quickly if needed. Be realistic about values and how long things take to sell.
Note which assets are essential for your job search or next role (like your laptop) versus nice-to-haves.
Check if you have any pending reimbursements, tax refunds, or other money coming in. Create a timeline of when you expect these funds.
Maintaining professional standing
Reference and relationship preservation
Document your key relationships immediately
Map out your relationship network in tiers:
Tier 1: Direct advocates (former bosses, key stakeholders who love your work).
Tier 2: Strong professional allies (teammates, cross-functional partners).
Tier 3: Broader network (customers, vendors, industry contacts) Why this structure? Because you'll need different approaches for each tier, and you can't maintain the same level of connection with everyone.
Secure your references now
Reach out to your best potential references right away with something like: "I've really valued our work together, and I'd be grateful if I could list you as a reference. Would you be comfortable speaking to my impact on [specific project/metric]?" Why now? Because people's memory of your contributions fades quickly, and you want them thinking about your wins while they're fresh.
Document their preferred contact methods and any time zone considerations. Little details matter, you don't want a potential employer calling your best reference at 6am their time.
Send each reference a brief bullet list of your key achievements under their leadership. Not to tell them what to say, but to remind them of specific impacts they might mention.
Communication strategy
Plan your departure messaging
Create three different departure messages:
Close colleagues (warm, personal, specific memories).
Professional network (factual, positive, future-focused).
Clients/external contacts (professional, emphasizing smooth transition) Why different versions? Because mixing these up can damage relationships - too personal with clients can seem unprofessional, too formal with close colleagues can seem cold.
LinkedIn strategy
Don't update your LinkedIn profile immediately. Here's why: Your activity will notify your entire network, and you want to control the narrative. Wait until you've:
Notified key contacts personally
Secured your references
Prepared your new professional narrative
When you do update, turn off activity broadcasts first. Make your updates gradually over several days rather than all at once. This looks more natural and doesn't scream "I just lost my job"
Professional membership management
Audit your professional assets
Review all your professional memberships and certifications. Create a spreadsheet noting:
Cost
Renewal dates
Whether they're personally owned or company-sponsored
Value for job search
Why track all this?
Because some memberships might be crucial for your job search, while others might be expensive luxuries you need to pause.
Handle certifications strategically
Check the status of any certification you earned through your company. Some certs become invalid when you leave, others stay with you. Why check now? Because maintaining certain certifications might require action within specific timeframes.
Download all certificates and completion records while you still have access. Companies sometimes revoke access to learning platforms immediately, and proving you completed something later can be a nightmare.
Industry presence maintenance
Plan your content strategy
Don't go silent, but don't overshare. Instead, plan one thoughtful LinkedIn post or comment every 7-10 days. This timing keeps you visible without looking desperate, and gives you time to craft quality insights.
Focus on sharing industry insights or helping others. For example:
Share interesting articles with your specific take
Offer genuine congratulations on peers' achievements
Contribute meaningfully to industry discussions The goal is to be seen as a stable professional continuing to add value, not someone scrambling for their next role
Stay connected to industry trends
Set up a simple system to track industry news and updates. In interviews, you'll need to show you're current with industry trends despite your employment gap
Create a focused list of:
Key industry newsletters (3-5 max).
Thought leaders to follow.
Professional blogs to monitor Don't try to follow everything - pick the sources that give you the most relevant insights for your job search.
Short-term income solutions
Contract work transition
Evaluate your immediate consulting potential
Look at your last 6-12 months of work. What problems did you repeatedly solve? What processes did you build? Why this reflection? Because your recent wins are your most sellable consulting offerings right now.
Make a quick list of companies similar to your past customers but smaller. They often need fractional CSM help. Think series A/B companies that can't afford full-time CSMs but need the expertise.
Create three tiers of consulting offerings:
Quick wins (health score setup, renewal process design).
Medium projects (QBR program development, CSM team training).
Ongoing support (fractional CSM for smaller clients) Why three tiers? Because you need options that can start bringing in money next week, not just long-term projects.
Package your expertise smartly
Turn your CSM playbook into sellable pieces. For example:
"Customer Health Score Workshop" (2-day engagement).
"Renewal Process Audit" (1-week project).
"CSM Onboarding Program Design" (2-week sprint) Why package it? Because selling specific solutions is easier than vague "consulting services," and you can name concrete prices.
Quick income streams
Leverage your technical skills
List out all the CS tools you know well (Gainsight, Salesforce, etc.). Why? Because tool expertise is often needed for short-term projects during implementations or migrations.
Look for companies posting jobs for these tools - they might need temporary help while searching for permanent hires.
Check if your tool vendors have implementation partner programs. Sometimes they need certified experts for overflow work.
Target transitional opportunities
Search for "maternity cover," "medical leave coverage," or "interim CSM" positions. Why these specifically? Because they:
Often need someone to start quickly.
Have defined end dates (good for consulting rates).
Value experienced CSMs who can jump in with minimal training.
Keep a spreadsheet of companies that recently raised funding. Series B/C companies often need experienced CSMs to cover growth spurts.
Knowledge monetization
Create valuable documentation
Look through your CSM files for processes or frameworks you created. What could be turned into templates or playbooks? Why? Because selling these as products requires less time than consulting.
Document your best practices for:
Customer onboarding
Health score design
QBR templates
Renewal playbooks
But remember: Only use your original work, nothing proprietary from past employers
Develop training materials
Think about what you wish you'd known as a new CSM. Why? Because while you're job hunting, you could create and sell training content for:
CSM certification prep
Tool-specific tutorials
New manager transitions
Start with quick-win content like checklist templates or process guides. These are easier to create and sell than full courses.
Financial bridge planning
Create your bridge budget
Calculate your minimum monthly income needed, then create three income scenarios:
Best case (full consulting rate).
Medium case (mix of project work).
Minimum viable (part-time or reduced rate work) Why three scenarios? Because you need to know your absolute bottom line for negotiating.
Set clear income goals
Break down your target monthly income into concrete projects:
Number of consulting days needed.
Number of deliverables/assets to sell.
Mix of long-term and short-term work Include time for business development - typically 20-30% of your work week. Why? Because people often forget to budget time for finding the next project.
Frequently Asked Questions
Q: I'm feeling overwhelmed and don't know where to start. What's absolutely crucial to handle in the first 24 hours?
The key is to focus on securing your professional assets before emotions take over. Your immediate priority should be protecting important documents and information that you'll need for your job search and future roles. Start by forwarding key emails about your accomplishments and performance to your personal email - you'd be surprised how many people forget this simple but crucial step. Write down everything from your departure conversation while it's fresh in your mind, including promises made and next steps discussed. Next, download your last few performance reviews and any training certificates - these will be invaluable for future interviews. Create a simple list of all the work tools and systems you need to log out of, and take clear photos of any company equipment you need to return. Remember, you can handle the emotional processing and longer-term planning in the coming days. Right now, focus on these concrete tasks that have firm deadlines or could be lost if you wait.
Q: My company is offering severance, but I'm not sure if I should negotiate or just accept it. What should I consider?
Think of severance negotiation as your last opportunity to advocate for yourself with your current employer. The standard baseline in many industries is two weeks per year of service, but this varies widely based on your role, industry, and circumstances. Your negotiating power often depends on several factors:
Standard severance in your industry (typically 2 weeks per year of service)
Your role's seniority and how hard it would be to replace you
Whether they're laying off multiple people (less negotiating power) or just you (more power)
What leverage you have (key customer relationships, specialized knowledge)
Your financial runway without severance
Remember that money isn't the only thing on the table. Many people focus solely on the dollar amount and miss opportunities to negotiate for valuable non-monetary benefits. Consider asking for extended healthcare coverage, which can be worth thousands of dollars, or outplacement services to help with your job search. Professional development funds can help you stay current while job hunting, and more flexible payment timing might help with your cash flow planning.
Q: Should I tell my customers I'm leaving? What's the best way to handle this?
Customer communications during a transition need to be handled with both professionalism and sensitivity. The best approach depends heavily on your company's policies and the nature of your customer relationships. Ideally, you'll want to work with your manager to create an approved message that maintains trust while ensuring a smooth handoff.
If direct communication is allowed, prioritize your outreach based on relationship strength and customer impact. Start with key stakeholders who deserve to hear the news personally, but keep these conversations professional and focused on their continuity of service. Avoid sharing personal details or future plans, as this can create uncertainty about their ongoing support.
Most importantly, document everything about your customer relationships before you leave. Create detailed handoff notes that include:
Current projects and priorities
Recent challenges or wins
Key stakeholders and their communication preferences
Upcoming renewal or expansion opportunities
Any promises made or commitments pending
Q: How do I maintain relationships with colleagues without seeming desperate for referrals?
Building and maintaining professional relationships requires authenticity and a long-term perspective. Think of it as tending a garden - you need to nurture connections consistently, not just when you need something. Start by sharing interesting industry articles with thoughtful comments that add value to the conversation. When you see colleagues celebrating work anniversaries or promotions, take a moment to write a personalized congratulation that references your shared experiences or their specific achievements.
The key is to engage meaningfully and regularly, but not excessively. Consider creating content that showcases your expertise and insights - this positions you as a thought leader rather than someone simply looking for their next role. When you do reach out directly, make it personal and specific. Instead of a generic "can you help me find a job" message, try sharing an insight about their company's recent developments or asking for their perspective on an industry trend.
Avoid common networking mistakes that can damage relationships. Don't send mass messages asking for referrals, and never share negative comments about your former employer, no matter how tempting it might be. Keep your LinkedIn activity professional and measured - too much activity can look desperate, while too little can make you seem disengaged.
Q: How should I handle my equity and stock options? The deadlines and rules feel overwhelming.
Stock options and equity can be one of the most complex parts of your departure. Many people don't realize that vested stock options often have a limited exercise window after leaving - typically 90 days - and once that window closes, you lose everything, even if the options were fully vested. Start by downloading your complete grant history and all documentation while you still have access to your equity platform.
Make a clear timeline of when your exercise windows close for each grant. Pay special attention to understanding:
Exercise prices for each grant
Current fair market value (if available)
Tax implications of exercising
Total cost to exercise your options
Any acceleration clauses that might apply
Remember that exercising options can come with significant tax consequences. Consider consulting a tax professional before making any decisions, especially if you have ISOs (Incentive Stock Options) that might trigger AMT (Alternative Minimum Tax).
Q: I'm worried about the gap in my healthcare coverage. What do I really need to know about COBRA and my options?
Healthcare continuity is more complex than most people realize, but there's good news: you have more time and options than you might think. The most important thing to understand about COBRA is that you have 60 days to decide whether to elect coverage, and it's retroactive to your last day of work. This means you can wait to see if you need it before paying those expensive premiums.
Let's break down your options:
COBRA: Expensive but maintains exact same coverage
Partner's insurance: Job loss is a qualifying event for mid-year enrollment
Healthcare marketplace: Also has special enrollment for job loss
Professional associations: Some offer group health plans
Short-term health plans: Can bridge gaps but watch for coverage limits
The smartest strategy is often to wait and see. If you get a new job quickly, you might not need COBRA at all. If something happens during the 60-day election period, you can retroactively elect COBRA and be covered. Just be sure to put aside enough money to cover the retroactive premiums if you need them.
Q: What's the current situation with non-compete agreements? I keep hearing they're being banned nationally.
The landscape for non-competes is currently in a period of significant change. In April 2024, the Federal Trade Commission (FTC) issued a final rule banning non-compete clauses nationwide. Here's what you need to know about the current situation:
For Most Workers:
Existing non-competes will no longer be enforceable after the rule takes effect
Your employer will be required to notify you that your non-compete will not be enforced
You don't need to take any action to invalidate your non-compete - it automatically becomes unenforceable
For Senior Executives (a small exception):
If you're a senior executive (earning more than $151,164 annually and in a policy-making position), existing non-competes can remain in force
However, even for senior executives, employers cannot create new non-compete agreements
This exception applies to less than 0.75% of workers
Important Timeline Notes:
The rule becomes effective 120 days after publication in the Federal Register
However, there are ongoing legal challenges to the rule
A district court has issued an order stopping the FTC from enforcing the rule, which the FTC has appealed
The FTC can still address non-competes through case-by-case enforcement
What This Means For Your Job Search:
Document any current non-compete restrictions you have
Watch for notification from your employer about non-enforcement
Keep track of the legal developments and effective dates
Consider consulting with an employment lawyer if you're in a senior executive position
Remember that employers can still protect their interests through:
Non-disclosure agreements (NDAs)
Trade secret laws
Other confidentiality provisions
The key takeaway is that while non-competes are being significantly restricted nationwide, there's still some uncertainty due to legal challenges. Stay informed about developments and consider seeking legal advice if you have specific concerns about your situation.
Q: Should I start consulting while I job hunt? How do I set this up quickly?
Consulting can be an excellent bridge strategy, but it needs to be set up thoughtfully. The fastest way to start is by identifying your "quick win" offerings - things you can do for companies with minimal setup or preparation time. Look at what you did repeatedly in your CSM role that other companies might need help with.
Create three tiers of offerings:
Quick Wins (1-2 weeks): Health score setups, renewal process design, QBR framework creation
Medium Projects (2-4 weeks): Customer success playbook development, onboarding program design
Ongoing Support: Fractional CSM services for smaller companies
Target companies that are:
Series A/B startups that need CS expertise but can't afford full-time hires
Growing companies implementing new CS tools or processes
Former partners or vendors who know your work
Companies posting CSM jobs that might need interim help
Remember to set up your consulting business properly:
Create a simple LLC if you plan to do this for more than a month
Set up a separate business bank account
Create a basic consulting agreement template
Decide on your rate structure (hourly vs. project-based)
Get clear on what company assets you can and can't use
Q: How do I handle references and recommendations in a way that sets me up for success?
Think of reference management as a strategic campaign, not just a box to check. The best references come from people who can speak specifically about your impact and abilities, not just confirm your employment. Start by making a list of potential references in three categories:
Direct managers who can speak to your day-to-day performance
Stakeholders who benefited from your work
Peers who can discuss your collaboration and teamwork
Reach out to your best potential references immediately with something like: "I've really valued our work together, and as I plan my next steps, I'd be grateful if you'd be willing to serve as a reference. Would you be comfortable speaking specifically about [project/impact/skill]?" This approach helps them understand exactly what you're hoping they'll highlight.
For each reference, create a brief bullet list of:
Projects you worked on together
Specific metrics or achievements they witnessed
Challenges you overcame
Skills they can verify
Send this as a gentle reminder when you know someone will be contacted - it helps them give a more detailed and impactful reference. Remember to keep your references updated on your job search progress and always let them know when they might be contacted.
Q: My company was just acquired/merged and I've been let go. Are there any special considerations I need to know about?
Acquisitions and mergers often come with unique challenges and opportunities. First, document everything about the transition - the official announcement, any promises made about retention or severance, and any new agreements you're asked to sign. Pay special attention to how the acquisition affects your equity - sometimes there are accelerated vesting provisions or cash-out options that you need to understand quickly.
Look carefully at:
Any new severance terms offered due to the merger
Changes to equity or stock option agreements
Different healthcare continuation options
Special retention bonuses or packages
Any new restrictions or agreements you're asked to sign
Also, recognize that acquisitions often lead to strong networking opportunities. Other companies often specifically look to hire talent during acquisitions, so timing your job search announcement strategically can work in your favor.
Q: The job market seems flooded with CSMs right now. How do I stand out when everyone has similar experience?
Standing out in a crowded market requires focusing on your unique impact and specializations rather than just your job title. Start by analyzing your CSM experience for areas where you went beyond the standard role:
Did you build specific programs or processes?
Have you worked with certain industries or company sizes?
Do you have expertise with specific CS tools or technologies?
Have you managed enterprise vs. SMB customers?
Did you handle technical implementations or integrations?
Create a clear narrative around your specialties:
"I specialize in turning around at-risk enterprise accounts"
"I build scalable customer success programs for high-growth startups"
"I develop technical onboarding programs for complex SaaS products"
Remember to highlight quantifiable achievements that demonstrate your unique value:
Specific revenue retention numbers
Customer health score improvements
Program launch results
Time-to-value reductions
Scale achievements (number of customers, revenue managed)
Q: My mental health is struggling with this transition. How do I manage this while maintaining my professional momentum?
This is a common but rarely discussed challenge. Job transitions can be emotionally taxing, and maintaining your professional effectiveness while managing stress requires intentional strategy. Start by creating clear boundaries between job search activities and personal time - treat your job search like a job itself with defined working hours.
Create a structured self-care plan:
Set specific times for job search activities
Schedule regular exercise or outdoor time
Maintain consistent sleep schedules
Plan social connections that aren't job-related
Consider professional support through EAP or therapy
For professional activities:
Break tasks into smaller, manageable chunks
Celebrate small wins daily
Keep a "wins journal" of positive feedback and achievements
Schedule regular check-ins with a mentor or friend
Join CSM communities for peer support
Many companies offer extended mental health benefits even after departure - check your separation agreement for details about continuing these services.
Q: I'm being asked to train my replacement before I leave. How should I handle this professionally while protecting my interests?
This is a delicate situation that requires balancing professionalism with self-protection. While it's important to maintain good relationships, you also need to protect your future opportunities. Start by getting clear written guidelines about what's expected - how many hours, what specific knowledge transfer is needed, and what the timeline looks like.
Create a structured handoff plan:
Document standard processes and procedures
Create customer status summaries
Build basic troubleshooting guides
Outline regular workflows
But be strategic about what you share:
Focus on information needed for basic role function
Don't share your personal relationship-building techniques
Keep your unique methodologies and frameworks private
Maintain ownership of processes you developed
Don't share personal contact lists or relationships
Consider negotiating for:
Additional compensation for training time
Extended benefits during transition
Positive references or recommendations
Flexible schedule for job searching
Written agreement about training scope and timeline
The key is to remain professional while being strategic about protecting your intellectual property and future opportunities.
Q: I have active customer relationships and expansions in progress. How do I handle my pipeline and commissions ethically while transitioning out?
This situation requires careful balance between protecting your earned compensation and maintaining professional integrity. Start by documenting every deal in your pipeline, including exact stages, next steps, and expected close dates. Create a clear timeline showing which deals could reasonably close before your departure and which will need transition.
Focus on three key areas:
Active deals likely to close before you leave
Expansions in late-stage discussions
Renewals that are in progress
Document everything in writing:
Current deal stages and status
All customer commitments made
Expected close dates and values
Your specific contributions to each deal
Email trails showing your involvement
Most importantly, review your commission agreement carefully for:
Post-departure payment terms
Pipeline ownership clauses
Commission splits on transitioning deals
Specific requirements for earning commission
Payment timing and dispute processes
The goal is to ensure you're fairly compensated for your work while setting up customers and your replacement for success. Remember to keep copies of all documentation related to your pipeline and commission arrangements for at least a year after departure.
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