After a few years in SMB sales, I’m trying to move up into mid-market or enterprise roles but not getting traction. Most hiring managers want someone who’s already done it. For those who successfully made that leap, how did you tell your story in a way that made the jump feel natural? Did you lean on metrics, client examples, or something else? I’m open to coaching myself up fast but need to figure out how to even get past the initial screen.

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Client examples helped me more than metrics. I walked through a few deals like case studies to show I understood stakeholder alignment, longer sales cycles, and layered objections.

When I moved from SMB to LE I found a manager that appreciated my tenacity. I took several members of his AE team out to lunch one on one and talked sales Strategy. I even partnered with them on some deals. I was in the channel.
Read The challenger customer book and familiarize yourself with the metrics behind gaining consensus in LE deals, the different roles, finding the mobilizer and map those concepts to how you did that in your accounts. I personally felt better with more autonomy and less managerial oversight when I sold in SMB. Lots of eyes on every deal in LE and you lose control of the outcomes due to the complexity of the sale and the matrix sales team . Be ready for that. You will make slightly more income.

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