AMA: Gainsight Senior Director of Customer Success, Meenal Shukla on Establishing the Customer Success Function

First 30 Days: Assessment & Foundation * Deep customer discovery: Interview 15-20 key customers across segments to understand their success metrics, pain points, and where they need support * Internal stakeholder alignment: Meet with Sales, Product, and Support to understand current customer handoffs and identify gaps * Data assessment: Evaluate what customer data we currently capture and what systems we'll need for proper CS measurement * Hire first CS Manager: Bring on someone with experience building CS programs who can help scale the team * Define initial success metrics: Create preliminary health scores based on product usage, support tickets, and renewal indicators 30-60 Days: Process & Playbooks * Launch pilot program: Select 15-20 customers for high-touch CS engagement to test approaches * Develop onboarding playbook: Create a structured process to accelerate time-to-value for new customers * Build QBR framework: Design a quarterly business review template that demonstrates clear value * Implement health scoring system: Roll out automated customer health tracking to identify at-risk accounts. Use tools like Staircase.ai to determine relationship gaps, sentiment issues and churn risks. * Develop escalation paths: Create clear protocols for handling customer issues that require cross-functional support * Hire 2-3 additional CSMs: Begin scaling the team with focus on specific customer segments 60-90 Days: Scale & Optimization * Expand program coverage: Roll out the CS model to a broader customer base with a tiered approach (high-touch, medium-touch, tech-touch) * Launch proactive intervention program: Begin outreach based on early warning indicators from health scores * Develop customer advocacy program: Identify champions and create pathways to testimonials, case studies, and referrals * Implement success planning: Create joint customer roadmaps with clear milestones and value indicators * Establish ROI framework: Develop clear metrics showing CS impact on retention, expansion, and overall revenue * Present CS roadmap: Share 6-12 month plan with executive team including resource requirements and expected outcomes

The most fundamental surprise is often how establishing CS requires comprehensive organizational change management—not just building a team, but reshaping company culture around customer outcomes. When transitioning from an established CS organization to building one from scratch, several surprising challenges often emerge: 1. Resistance to Customer Centricity * Unexpected opposition: You'll be surprised by how many teams operate without considering customer outcomes * Product-first mentality: Many organizations still build features first and consider customer success as an afterthought * Sales disconnection: Finding that Sales sees their job as "done" at signature, with little consideration for post-sale success 2. Data Fragmentation & Visibility Issues * Missing customer intelligence: Discovering critical customer data is scattered across spreadsheets, emails, and people's heads * Incomplete journey tracking: Realizing nobody has mapped the full customer lifecycle or measured key transition points * Usage blindness: Learning your product lacks basic instrumentation to understand how customers actually use it 3. Resource Struggles * ROI skepticism: Having to repeatedly justify CS investments before you have established metrics * Responsibility without authority: Being accountable for retention without control over product roadmap or support resources * Expectation misalignment: Leadership expecting immediate impact while proper CS foundations take time to build 4. Cultural Transformation Challenges * Breaking reactive patterns: Finding teams deeply entrenched in firefighting rather than prevention * The "overhead" perception: Discovering CS is viewed as a cost center rather than a revenue driver * Success ownership confusion: Unclear boundaries between CS, Support, Services, and Account Management 5. Customer Expectation Reset * Relationship recalibration: Customers who have operated without CS suddenly expecting immediate transformation * Trust rebuilding: Inheriting customer relationships that may have accumulated frustrations and unmet expectations * Value articulation: Discovering customers don't understand how to measure their own success with your product

Small Company CS * Generalist roles: CSMs handle everything from onboarding to renewals to support * Direct executive involvement: Founders/C-suite often engage with key customers * Rapid iteration: Can quickly adapt processes based on customer feedback * Limited resources: Creative solutions with minimal tools and headcount * High visibility: Each customer represents a significant percentage of revenue * Relationship-driven: Heavy reliance on personal connections and flexibility * Reactive tendencies: Often addressing issues as they arise rather than proactively * Minimal segmentation: Similar service levels across most customers * Shared responsibility: CS functions overlap with sales, support, and product Large Company CS * Specialized roles: Dedicated onboarding specialists, CSMs, renewals managers * Structured processes: Standardized playbooks and escalation paths * Tiered service models: Clearly defined engagement levels based on contract value * Data-driven approach: Sophisticated health scoring and predictive analytics * Platform investment: Purpose-built CS tools with extensive integration * Scale-oriented: Designed to handle hundreds/thousands of customer relationships * Cross-functional teams: Dedicated resources from product, support, and services * Global coverage: Regional CS teams aligned to customer geographies * Revenue focus: Clear metrics on retention, expansion, and CS-influenced growth

Key Indicators You're Ready * 10-20 paying customers: Enough accounts to justify dedicated attention * Recurring revenue model: You have ongoing relationships to maintain * Post-product-market fit: Your offering solves a proven need consistently * Initial churn concerns: You've experienced or anticipate renewal challenges * Complex onboarding: Your product requires significant setup/training * Customer retention is vital: Your unit economics depend on multi-year relationships Financial Readiness Signals * $500K-$1M ARR: Typically provides enough revenue foundation * Expansion opportunity: Customers have natural upsell/cross-sell potential * Renewal cycle approaching: First wave of customers nearing renewal decisions

When joining a small but growing team to improve customer success processes, focus on strategic implementation that balances immediate impact with scalable foundations: Prioritize High-Impact Quick Wins * Customer journey mapping: Document the current experience to identify immediate friction points * Basic health scoring: Start with simple red/yellow/green classifications using available data (engagement, support tickets, renewals) * Standardize onboarding: Create repeatable templates even if basic; consistency drives efficiency * Regular customer touchpoints: Implement structured check-ins at critical moments (post-onboarding, pre-renewal) Build for Scale While Staying Lean * Choose versatile tech: Select CS platforms that can grow with you—avoid over-engineering early * Design tiered service models: Create different engagement levels (high/medium/tech-touch) to efficiently allocate resources * Templatize everything: Build playbooks for common scenarios that anyone can follow * Cross-train team members: Develop versatile CSMs who can handle multiple customer segments Establish Measurement Foundation * Define leading indicators: Identify early warning signs of churn before they become critical * Track time-to-value: Measure how quickly customers achieve their first meaningful outcome * Set engagement benchmarks: Establish healthy usage patterns by customer segment * Connect CS metrics to revenue: Show direct impact on retention and expansion to secure resources Build Cross-Functional Alignment * Create feedback loops with Product: Establish regular channels to share customer insights * Clear handoffs with Sales: Define exactly when and how customers transition to CS * Support escalation paths: Design clear protocols for when issues need specialized attention * Executive visibility: Regular reporting to leadership on customer health and CS impact Focus on Proactive Engagement * Develop early warning system: Simple alerts for at-risk behaviors * Success planning: Work with customers to document their goals and milestones * Value reviews: Regular check-ins showing ROI customers have achieved * Expansion identification: Process for flagging accounts ready for additional products/service

Establish a Joint Metrics Workshop 1. Bring together CS and Sales leadership for a dedicated session focused solely on metrics alignment 2. Start by identifying what each team currently measures and why 3. Look for overlap and gaps in current measurement approaches 4. Define what "good" looks like from both perspectives Design Collaborative KPIs That Matter to Both Teams * Renewal rate with shared accountability * Expansion rate with clear attribution models * Customer lifetime value with joint ownership (this one is hard) Create Operational Connection Points * Weekly pipeline reviews including both new and expansion opportunities * Monthly account health briefings where Sales learns about customer status * Quarterly business planning with joint account strategies * Unified customer meeting cadences where appropriate

Essential Manual Tracking Tools * Customer health database: Create a central spreadsheet (Google Sheets/Excel) with: * Basic account info (contract value, renewal date, key contacts) * Health indicators (color-coded red/yellow/green) * Usage metrics pulled manually from your product * Engagement tracking (last contact, QBR dates) Risk indicators and mitigation plans * Renewal pipeline tracker: Separate spreadsheet focusing on: * Upcoming renewals by quarter * Expansion opportunities * Renewal probability scores * Historical trends by segment * Customer engagement log: Document all meaningful interactions. (There are tools available in the market that can automatically do this for you, like Staircase.ai). * Meeting notes in a shared drive * Email summaries of key discussions * Support ticket history * Product feedback collected The breaking point typically occurs around: * 20 accounts per CSM for high-touch B2B relationships * ~200-300 total accounts across your CS organization * 10+ CSMs Signs you've outgrown manual tracking: * CSMs spending 20%+ of time just maintaining tracking systems * Renewal forecasting becoming consistently inaccurate * Difficulty identifying at-risk accounts before problems escalate * Inability to correlate product usage with renewal likelihood * Leadership lacks clear visibility into customer health trends