13 months ago, our average contract value was $9K. Today, it’s $50K—with six-figure deals hitting every quarter. This isn’t a fluke. It’s the result of deliberate, repeatable processes we engineered inside the business.
This is our playbook—5,000 words of raw, unfiltered strategy, tactics, and execution that led us here.
1. Changing the Way We Approached Discovery
We realized that enterprise deals don’t start with a demo. They start with a conversation that challenges the buyer’s worldview. We stopped running discovery like an interview and started running it like a consulting session.
What We Changed:
- From script to strategy: We ditched templated questions. Every AE had a pre-call brief tailored to the vertical, buying stage, and persona. We did real homework: 10-Ks, LinkedIn profiles, blogs, podcasts, etc..
- Multi-layered questions: Discovery had 3 levels: surface ("what tools do you use?"), strategic ("how do you report to the board?"), and political ("who owns pipeline creation internally?").
- Reframing pain: Instead of "what's not working," we asked "what would your CEO say if you missed pipeline this quarter?" We made problems visceral.
- Pre-demo assignments: For key accounts, we asked prospects to share their internal deck or funnel model before a demo. We showed up with insights, not slides.
How It Impacted ACV:
- We uncovered more cross-functional needs (RevOps, Sales, Finance).
- We anchored value to outcomes, not features.
- We earned permission to run multithreaded cycles earlier.
2. Running Real Enterprise Deal Cycles
You can’t fake an enterprise deal. We learned how to run real, political, 6-figure deal cycles that didn’t just close—but closed strong.
Our Playbook:
- Mutual action plans (MAPs): No deal moved without one. AEs co-created MAPs with buyers in the first week. Dates, milestones, stakeholders, redlines.
- Stakeholder orchestration: We mapped the buying committee early: champions, influencers, blockers, and budget owners.