How to Upsell Premium Support Tiers to Legacy SaaS Customers
Designed for Customer Success Managers and Account Executives at mid-market SaaS firms with >3 years tenure, tasked with converting legacy clients to premium support tiers amid stagnant renewals. to spark real collaboration and high-energy learning.
A 75-minute virtual workshop for seasoned CSMs and AEs. Participants report frustration with legacy accounts stuck on outdated support contracts; they struggle with value articulation and face frequent price pushback. The workshop aims to build confidence, spark creativity, and deliver practical upselling scripts.
Hidden Impact Quiz
Begin with a rapid-fire, interactive quiz featuring surprising stats about customer outcomes from different support tiers (e.g., 'Customers with premium support resolve tickets 3x faster — true or false?'). Participants answer live; reveal answers immediately and discuss why these outcomes matter.
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Why this works
Leveraging curiosity and data-driven surprise builds immediate engagement and sets a factual foundation for later persuasion.
Myth-Buster Gallery
Showcase common misconceptions legacy customers hold about premium support ('It’s just glorified ticket escalation'). Invite participants to walk through a virtual gallery of customer quotes and vote: Myth or Fact? After voting, clarify each statement and debunk with evidence.
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Why this works
Addressing misconceptions head-on helps participants prepare for real conversations, and cognitive dissonance primes deeper learning.
Silent Script Swap
Distribute two anonymized email snippets: one successful, one unsuccessful upsell. Participants read silently and jot down what worked or flopped in each. Then, share observations in chat (no pressure to speak aloud), seeing patterns emerge across the group.
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Why this works
Low-pressure solo participation builds comfort and allows introverts to contribute, while collective analysis surfaces best practices organically.
Lightning Pitch Battles
Split into breakout groups. Each group crafts a 30-second premium tier pitch for a skeptical legacy customer persona. Groups deliver their pitches rapid-fire, and the rest cheer, vote, and offer one improvement suggestion. Fast, fun, and energetic.
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Why this works
Competitive, collaborative activity boosts energy and hones concise messaging—participants get immediate peer feedback.
‘What Would You Do?’ Dilemma
Pose a real-world dilemma: ‘Your legacy client’s contract is up and they say, “We’ve done fine with basic support—we don’t see the need.”’ Participants choose from three possible responses (e.g., empathy, data-driven challenge, escalation) and discuss consequences in pairs.
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Why this works
Applying learning to realistic situations cements skills and surfaces nuanced approaches—dilemmas deepen critical thinking.
Personal Upsell Story Circle
Invite participants to share (via chat or voice) a time they successfully—or unsuccessfully—upsold a legacy customer. Prompt: ‘What made it work, or what held you back?’ Facilitator encourages connection, empathy, and practical takeaways from each story.
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Why this works
Active reflection and sharing create personal relevance, deepen learning, and foster community; storytelling solidifies new skill adoption.
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