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March 11, 2025

First 90 Days as a Customer Success Leader: Complete Checklist

Start strong as a Customer Success leader by focusing on these key steps in your first 90 days:

  1. Build Trust and Learn (Days 1–30):
    • Meet key stakeholders (executives, sales, marketing, product, finance, and your team).
    • Map current workflows, assess processes, and review metrics (e.g., NPS, churn rates).
    • Talk to customers to understand their needs and goals.
  2. Develop a Strategy (Days 31–60):
    • Prioritize impactful changes like improving onboarding or standardizing playbooks.
    • Choose 3 key metrics to track (e.g., Customer Health Score, Net Revenue Retention).
    • Create a 12-month plan with quarterly goals.
  3. Execute and Measure (Days 61–90):
    • Launch new programs (e.g., customer health monitoring, enhanced onboarding).
    • Track progress with leading and lagging indicators.
    • Foster cross-team collaboration with regular updates and shared goals.

Quick Overview

Phase Timeline Key Focus Example Actions
Learn Days 1–30 Build relationships Meet stakeholders, review workflows, talk to customers
Strategize Days 31–60 Plan improvements Prioritize changes, set metrics, create a roadmap
Execute Days 61–90 Implement and measure Launch programs, track metrics, refine processes

Pro Tip: Focus on trust-building and actionable insights early on. This sets the foundation for lasting success in your role.

Month 1: Learn and Connect

Use your first 30 days to build relationships and gather crucial insights. This groundwork will set you up to make well-informed decisions and implement impactful changes down the line.

Connect with Key People

Strong relationships across the organization are essential for success. Schedule focused meetings with key stakeholders to align on goals and expectations:

Stakeholder Group Meeting Focus Discussion Points
Executive Team Strategic Alignment Company vision, growth targets, and Customer Success (CS) role expectations
Sales & Marketing Pipeline & Messaging Customer acquisition strategies and handoff processes
Product Team Roadmap & Features Development priorities and customer feedback loops
Finance Metrics & Resources Budget allocation, revenue targets, and reporting needs
Customer Success Team Current Operations Day-to-day challenges and team capabilities

Map Current CS Workflows

Take time to document existing workflows and pinpoint areas for improvement. Focus on these key aspects:

  • Process Assessment: Review the customer journey (onboarding, check-ins, renewals) to identify gaps or inefficiencies.
  • Metrics Review: Evaluate critical performance indicators such as:
    • Customer health scores
    • Net Promoter Score (NPS)
    • Churn rates
    • Customer satisfaction metrics
    • Revenue metrics (e.g., expansion and retention)
  • Tech Stack Evaluation: List all tools and systems your team uses, noting how they integrate and how data flows between platforms.

Talk to Customers

Conversations with customers can provide essential insights to guide your strategy. Here are two key questions recommended by Douglas S. Miller, VP of Customer Success at AirPR Software:

"What can my company do to better serve your needs?"
"How do you need to transform your business over the next 18 months, and how can I help?"

Structure these discussions around three main areas:

Focus Area Purpose Sample Questions
Current State Understand the existing relationship Why did you choose us? What's working well?
Pain Points Identify improvement areas What challenges are you facing? How can we help?
Future Goals Align with customer objectives What does success look like? What are your 12-month priorities?

These insights will be invaluable as you begin strategic planning in Month 2.

Month 2: Plan Your Strategy

Take what you learned in Month 1 and turn it into actionable steps to improve customer success. Focus on identifying key changes that deliver both immediate results and set the stage for long-term growth.

Focus on Key Changes

Prioritize changes that create the biggest impact for customers while improving team efficiency.

Area Initiative Impact
Customer Journey Streamline onboarding Faster time-to-value for customers
Team Operations Standardized playbooks Better team efficiency
Technology Stack Consolidate reporting Clearer insights, lower costs
Customer Health Early warning system Prevent churn proactively

Choose Metrics That Matter

Once your priorities are clear, decide on the key metrics to measure success. Mike Begala, MBA, offers a great perspective:

"Do not worry about the metrics. Worry about solving the problem for the customer. If you get caught up in a thousand metrics, you will always be looking at the wrong thing. Care for the customer as if it meant your life. Every touch point, every interaction. Reduce the friction, increase the empathy."

Stick to just three critical metrics to avoid getting overwhelmed:

  • Customer Health Score: Combine data like product usage, support tickets, and customer engagement.
  • Net Revenue Retention: Measure how expansions and churn affect recurring revenue.
  • Time to First Value: Track how quickly new customers reach their initial goals.

Map Out a 12-Month Plan

Research shows that reducing churn by just 5% can boost profits by up to 25%. Use this insight to guide your quarterly objectives:

Q2 2025

  • Launch a standardized onboarding process.
  • Implement a customer health scoring system.
  • Start regular voice-of-customer sessions.

Q3 2025

  • Introduce customer success playbooks.
  • Begin quarterly business reviews.
  • Launch a customer advocacy program.

Q4 2025

  • Automate customer health monitoring.
  • Develop a digital customer success program.
  • Plan for team expansion resources.

Q1 2026

  • Roll out a proactive expansion program.
  • Scale digital customer success efforts.
  • Launch an advanced analytics dashboard.

Month 3: Take Action

With your strategic plan from Month 2 in place, it’s time to put your ideas into motion. This month is all about execution.

Start New Programs

Kick off these programs to drive results:

Program Type Focus Area Expected Outcome
Customer Health Monitoring Automated scoring system Detect risks early
Onboarding Enhancement Standardized playbooks Shorten time-to-value
Digital CS Program Self-service resources Boost scalability
Voice of Customer Regular feedback sessions Strengthen retention

Check Progress

Keep a close eye on how your initiatives are performing by using both leading and lagging indicators. For example, Adobe saw a 30% drop in voluntary turnover after introducing regular manager-employee check-ins.

"Tracking team progress is more than just ticking checkboxes; it's understanding where your team stands, identifying any potential roadblocks, and ensuring everyone works toward shared goals."

Focus your reviews on these three areas:

  • Customer Impact: Look at changes in customer health scores and engagement levels.
  • Team Performance: Measure efficiency gains and how well playbooks are being used.
  • Business Outcomes: Evaluate retention rates and expansion opportunities.

Regular reviews ensure your team stays on track and aligned with your goals.

Set Team Communication

Clear and consistent communication is key. Sal Pugliese highlights its importance:

"Sustained and open communication within your teams is a key component for a successful project, especially when it comes to promptly identifying and addressing potential risks. This proactive approach ensures a more Agile and adaptive project management process."

Use a structured approach to team communication:

  • Daily Standups: Quick 15-minute updates to discuss progress and roadblocks.
  • Weekly Progress Reviews: Dive into key metrics and address blockers.
  • Monthly Strategy Sessions: Adjust priorities as needed.
  • Quarterly Business Reviews: Evaluate overall performance and long-term goals.

Leverage project management tools to keep everyone on the same page and focused on high-priority tasks. This ensures transparency and accountability across the team.

Working Across Teams

When launching new programs, prioritize collaboration between teams to boost overall results.

Cross-departmental teamwork can save considerable time and money. Without it, siloed teams may lose up to 20 hours a month, which could cost a 200-person company $1.5 million annually.

Partner with Sales and Product Teams

Work closely with Sales, Product, and Marketing teams through clear communication and shared goals. Here's how successful companies collaborate:

Department Focus Area Key Actions
Sales Customer Insights Share success stories, coordinate handoffs, and align on ideal customer profiles.
Product Feature Development Provide feedback, track shared metrics, and prioritize customer needs.
Marketing Customer Engagement Coordinate campaigns, share insights, and create customer success content.

To strengthen these partnerships, schedule regular check-ins:

  • Weekly CS-Sales Syncs: Discuss renewals and review customer health scores.
  • Bi-weekly Product Reviews: Share feedback and evaluate feature requests.
  • Monthly Joint Planning: Align on priorities and allocate resources effectively.

"Instead of thinking in a silo, really look at how customer success and sales can better partner together or how you can leverage marketing as a tool and as a resource to drive customer engagement."

  • Maranda Dziekonski, Chief Customer Officer at Swiftly

Set Up Team Updates

Once your strategy is in place, regular updates between teams help maintain alignment without overwhelming anyone.

Digital Collaboration Tools:

  • Use platforms like Slack or Microsoft Teams for dedicated project channels.
  • Share documents in centralized repositories.
  • Leverage project tracking tools that are accessible to all stakeholders.

Meeting Best Practices:

  1. Focus on problem-solving rather than status updates.
  2. Involve active participation from all relevant departments.
  3. Track action items and ensure follow-ups are completed.

"CS needs Product to continue building tools and features customers will love, and Product needs CS to continue driving adoption and customer happiness."

When submitting feature requests, include:

  • Business use cases.
  • Expected impact on customer results.
  • Supporting data or examples.
  • Priority level based on customer demand.

Research shows that top-performing organizations are 5.5x more likely to reward effective collaboration at all levels. Make teamwork a measurable part of performance reviews and celebrate cross-functional successes often.

Tools and Data Management

Your tech stack and data processes play a huge role in driving customer success initiatives. They empower teams to take proactive steps and deliver better outcomes.

To succeed, you need tools and systems that integrate seamlessly and provide clear, actionable customer insights.

Review Your Tech Stack

When reviewing your workflows, it’s equally important to evaluate whether your tools can fully support those processes.

Tool Category Primary Function Key Features to Look For
CS Platform Customer Health Monitoring AI-driven insights, workflow automation, custom health scores
Data Analytics Performance Tracking Real-time dashboards, predictive analytics, custom reporting
Integration Hub Data Consolidation CRM sync, support ticket integration, communication tools

When choosing customer success software, look for solutions that:

  • Are easy to implement
  • Offer strong reporting capabilities
  • Allow customizable workflows
  • Integrate smoothly with your current tools

"ClientSuccess has been a huge help for our company as we have grown and scaled our Customer Success efforts over these last years. Being able to customize the software to the way we want to engage and evaluate customers has been a tremendous help to our CSMs and our executive team." - Christian Kuehne, EVP of Athletic Organizations at GamePlan

Use Data for Decisions

A data-driven approach is essential for understanding and improving the customer journey. Tracking the right metrics ensures your team stays ahead.

Key metrics to monitor:

  • Onboarding Analytics: Measure how quickly customers reach value and track adoption rates.
  • Feature Usage: Identify which product features deliver the most value.
  • Customer Health: Keep tabs on engagement levels and potential risks.
  • Renewal Indicators: Analyze patterns that signal renewal likelihood.

"The ability to look at all actions through the lens of revenue is paramount. If my team is able to stay ahead of churn pitfalls that were previously unpredictable, that's a win and puts a clearer lens on the opportunities to protect and grow customer revenue." - Conor Nolen, Drata

Set up a regular reporting schedule to keep everyone aligned:

  • Daily: Health score updates
  • Weekly: Adoption trends
  • Monthly: Core metrics review
  • Quarterly: Business impact analysis

Make sure key data is accessible to your entire team. As Totango Team explains, "Using customer data to illuminate the road ahead is always going to be far more effective than winging it or blindly assuming that what has worked in the past will continue to work in the future."

To turn data into action:

  • Automate alerts for accounts at risk.
  • Build dashboards for critical performance indicators.
  • Regularly check data quality.
  • Set up escalation protocols for flagged issues.

These steps ensure your team stays aligned and can make informed, impactful decisions.

Conclusion

90-Day Checklist Summary

The first 90 days are critical for setting yourself up for long-term success. Here's a quick recap of the key milestones you've achieved:

Timeline Core Focus Areas Key Achievements
Month 1 Information Gathering Gained product knowledge, built team connections, and gathered customer insights
Month 2 Strategy Development Defined success metrics, improved processes, and developed annual plans
Month 3 Program Implementation Launched new initiatives, tracked progress, and aligned your team

This summary highlights the groundwork you've laid for growth and progress.

Next Steps

Now that you've established a solid foundation, it's time to refine, expand, and strengthen your strategies. Stay focused on these key priorities:

Refine Your Customer Success Framework
Create a system to collect and act on customer feedback. This will help you spot trends and adjust your strategies as needed.

"The business world is ever-evolving, and so are your customers' needs. Staying agile, being open to feedback, and being willing to pivot your strategies are essential to a successful Customer Success function. This is not a one-time effort but an ongoing journey of improvement and adaptation."

Expand and Streamline Operations
Focus on scaling through standardization and automation. This includes:

  • Streamlining onboarding processes
  • Automating health monitoring
  • Setting clear escalation protocols
  • Establishing repeatable QBRs

Build Stronger Cross-Functional Relationships
Collaboration across departments is key to ensuring Customer Success is a company-wide effort. Prioritize:

  • Aligning with the product team for feature updates
  • Partnering with sales for smooth handoffs
  • Working with support to deliver consistent service

Customer Success leadership is a dynamic role that requires constant growth and adaptation.

"Customer Success is more than just a department; it's the heartbeat of any thriving company."

Keep building on your progress while evolving your strategies to meet new challenges and opportunities.

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