Running Competitive Displacement Campaigns Against Legacy Tech Monopolies
Designed for Account executives and customer success managers at SaaS companies tasked with displacing entrenched legacy vendors (e.g., Salesforce, Oracle, SAP) in mid-market or enterprise deals to spark real collaboration and high-energy learning.
A 75-minute virtual workshop for experienced sales and CS professionals. Participants often lose deals to deeply entrenched legacy vendors because prospects fear switching costs, doubt the challenger’s reliability, or feel personal loyalty to the status quo. Many struggle to go beyond feature battles and provoke meaningful commercial urgency.
Monopoly Mindset Icebreaker
Kick off with a rapid-fire poll: 'Which legacy vendor is your team's biggest nemesis—and why?' Instantly display anonymized results and invite 2-3 people to share surprising reasons (e.g., 'deep IT ties,' 'fear of losing integrations'). This builds curiosity around the emotional and political forces at play.
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Why this works
By surfacing real competitor perceptions, you prime the group to think beyond product features and tap into the undercurrents shaping buy decisions.
Myth-Busting Matrix
Present a slide with the top 5 myths prospects believe about legacy tech (e.g., 'Switching is riskier than staying'). Read each out loud, then ask, 'Which one has killed your deals?' Collect quick chat responses and challenge the group: 'Why might YOUR prospects cling to these beliefs—are we missing something?'
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Why this works
Confronting misconceptions head-on helps participants realize the need to reframe the conversation, not just out-feature the incumbent.
Switching Stories Jamboard
On a collaborative board, participants drag-and-drop digital sticky notes to map every micro-step in a customer’s transition from legacy to challenger. No detail is too small! This low-pressure brainstorm reveals hidden friction—and unexpected moments of delight.
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Why this works
Visualizing the customer journey together lowers stakes, as everyone contributes informally. It exposes overlooked barriers and creative advocacy moments.
Rapid-Fire 'Objection Karaoke'
Turn up the energy with a lightning round: one facilitator reads a classic legacy-loyalist objection ('We’ve used Oracle forever—why change now?'), then tosses a foam ball (or picks from the Zoom grid) to a participant to give a 20-second challenger response. Rotate fast, building both skill and camaraderie.
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Why this works
This high-energy call-and-response format gets everyone’s adrenaline up and rehearses real-world agility, not canned scripts.
The CIO’s Dilemma Case
Share a vivid, real-world scenario: a Fortune 500 CIO must choose between your innovative SaaS and a 15-year legacy vendor. Reveal snapshots of their internal email threads—budget worries, hidden champions, board skepticism. Small groups debate: 'What should the CIO do, and how would you win them over?'
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Why this works
Wrestling with authentic dilemmas puts participants in the buyer’s shoes, fostering empathy and strategic thinking.
My 'Monopoly Move' Commitment
Invite each participant to privately write down one courageous action they'll take to challenge a legacy vendor in their next pipeline opportunity—then share aloud or in chat. Encourage specificity: 'I’ll ask the CTO, “What’s the business cost of waiting 2 more years?”' Close with a group commitment chant or digital pledge wall.
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Why this works
Personal commitments, voiced publicly, drive accountability and increase follow-through by building social proof.
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