Customer Upsell & Expansion Opportunity Workflow

A structured 10-15 day workflow for customer success and sales teams to identify, qualify, and pursue upsell opportunities while professionally handling downgrades. What this template does: Guides your team through a systematic approach to revenue expansion - from analyzing account health and qualifying opportunities, through personalized outreach, to tracking results and handling downgrades gracefully. When to use: • Contract renewal periods approaching • Customers showing high product engagement • Accounts expressing interest in additional features • Need to standardize expansion sales process Benefits: • Data-driven expansion decisions • Consistent qualification criteria across team • Professional handling of all scenarios including downgrades • Continuous improvement through result tracking Template Details: • Steps: 7 • Duration: 10-15 days • Automations: 1 (auto-routes qualified opportunities) • Best for: Customer Success, Account Management, Sales

7 steps 1 automations

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Process steps

Review expansion opportunities

2 day from previous step

task

Analyze customer data to find natural upgrade paths. Key data sources to review: • Product usage metrics and engagement levels • Account health scores and NPS feedback • Contract renewal dates and terms • Feature requests and support ticket history Priority signals for expansion: • High feature adoption rate • Growing team size or user count • Expressed interest in premium capabilities • Approaching contract renewal window Output: Ranked list of expansion-ready accounts with supporting data points for each opportunity.

Qualify and score the opportunity

3 day from previous step

task

Score each opportunity to prioritize your efforts effectively. BANT qualification framework: • Budget: Does the customer have budget authority? • Authority: Are you speaking with decision-makers? • Need: Is there a genuine business need for expansion? • Timing: Is now the right time (contract renewal, fiscal year)? Categorize opportunities: • Quick wins: High fit, ready to buy - route to AE immediately • Nurture: Good fit but timing not right - schedule follow-up • Not qualified: Poor fit - document and deprioritize Note: Completing this step automatically routes qualified opportunities to the next phase.

Identify specific upsell paths

4 day from previous step

task

Map each qualified account to the right upgrade option. Common upsell paths: • Tier upgrade: Moving from Basic to Pro or Enterprise • Seat expansion: Adding more users or teams • Feature add-ons: Premium integrations, advanced analytics, priority support • Usage increase: Higher limits, additional storage, more API calls Important timing considerations: • Never push upgrades on struggling customers • Align proposals with budget cycles • Look for natural expansion triggers (new projects, team growth) Document for each account: Recommended path, estimated value, key decision-maker, and best timing for outreach.

Prepare personalized outreach

6 day from previous step

task

Craft a value-focused approach tailored to each customer. Research before outreach: • Review their specific usage patterns and pain points • Note any recent support tickets or feature requests • Understand their business goals and industry context • Identify their key stakeholders and decision process Build your value proposition: • Focus on outcomes, not features • Use their language and terminology • Reference their specific situation and goals • Prepare ROI data or case studies from similar customers Avoid common mistakes: • Generic pitches that ignore their context • Leading with price instead of value • Pushing products they do not need

Conduct the expansion conversation

10 day from previous step

task

Have a consultative conversation focused on their success. Conversation structure: 1. Start by asking how things are going with current usage 2. Listen actively for pain points your upsell addresses 3. Present options tied to their specific needs 4. Discuss value and outcomes, not just pricing 5. Handle objections honestly and transparently Common objections and responses: • Budget concerns: Discuss ROI and payment flexibility • Timing: Offer to schedule for better timing • Need buy-in: Offer to present to stakeholders • Not sure of value: Propose a trial or pilot Remember: No pressure tactics. A declined upsell today can become an expansion next quarter.

Handle downgrades professionally

12 day from previous step

task

Turn downgrades into relationship-building opportunities. When a customer needs to downgrade: • Make the process easy and friction-free • Ask for honest feedback about the reason • Listen without arguing or applying pressure • Document the reasons for future analysis Keep the relationship positive: • Thank them for their business at any level • Explain what they will still have access to • Offer to check in when circumstances change • Set a reminder to follow up in 6-12 months Key insight: Today s downgrade can become next year s expansion. Customers remember how you treated them during difficult moments.

Track results and optimize strategy

15 day from previous step

task

Use data to continuously improve your expansion approach. Metrics to track: • Expansion revenue (MRR/ARR added) • Conversion rate by opportunity type • Average deal size and time to close • Win/loss reasons by category • Customer health score changes post-expansion Analyze patterns: • Which customer segments expand most? • What messaging resonates best? • Which objections appear repeatedly? • What is the optimal timing for outreach? Share learnings with the team: • Document successful approaches • Update talk tracks based on results • Identify training opportunities • Celebrate wins and analyze losses