ClearPath Conversations

17 - How to Introduce CS-Led Upsell Without Feeling Salesy


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In this episode of ClearPath Conversations, Mark Bernardin tackles one of the most uncomfortable topics for Customer Success Managers: how to drive expansion revenue without abandoning the advisory role that makes them effective. Drawing from over a decade managing enterprise accounts at companies like Cofense, Swimlane, and Palo Alto Networks, Mark breaks down the systematic approach that enabled him to drive over $1M in expansion revenue while strengthening customer relationships.

Mark opens with a coaching story from his time mentoring CSMs at Palo Alto Networks. When a CSM came to him with a fifteen-slide product deck, Mark stopped him with one question: "What problem does this solve for them?" The CSM couldn't answer. This moment reveals the core mistake most CSMs make with expansion - leading with product instead of problems. Mark guided him through a discovery-first approach that closed a $47,000 expansion while strengthening the relationship.

The episode introduces Mark's 5-Part Expansion Conversation Framework from "The CSM's Personal Playbook." Part one: Context Setting - referencing observed signals without pitching. Part two: Situation Exploration through open-ended questions. Part three: Impact Discovery, helping customers quantify business implications. Part four: Solution Connection, presenting capabilities as options. Part five: Next Steps Agreement, establishing clear timelines.

Mark illustrates with a detailed Cofense example where he managed 50+ enterprise accounts. After noticing a customer repeatedly asking about SIEM integration, Mark prepared before their next meeting. He pulled usage data, reviewed incident response metrics against industry benchmarks, and analyzed SOC workflows. When they met, Mark showed findings: analysts spent $337,000 annually on manual work plus missed incidents due to detection delays. The $85,000 expansion was approved within two weeks.

Mark addresses CSM discomfort with expansion, reframing it as recognizing their unique position to identify opportunities. CSMs identify and validate; Sales handles commercial discussions.

The episode closes with a Swimlane example where Mark facilitated a peer conversation between two financial services VPs rather than pitching. By connecting a customer facing alert challenges with a regional bank that solved the same problem, Mark enabled authentic learning. The conversation covered implementation, resources, and a 40% reduction in response time. Two weeks later: $24,000 expansion.

Throughout, Mark emphasizes proactive preparation over reactive conversations, strategic peer facilitation over product presentations, and helping customers build internal business cases. The companion toolkit at ClearPathCX.com includes signal detection checklists, the conversation framework, IMPACT qualification criteria, and business case templates.

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ClearPath ConversationsBy ClearPath CX