Selling to the CIO - A case study

Stop Selling. Start Thinking Like a CIO

If your CRO is asking you to help sellers sell to C-level executives, and your instinct is to double down on sales tactics, you’re going to struggle. Selling harder isn’t the answer.

We partnered with a leading tech company to help their reps stop selling and start thinking like their customers. Here's what happened when we flipped the script.

The Context

Our client was a category leader in infrastructure and cybersecurity, with nearly two decades of dominance in the enterprise. Their sales team had deep credibility with IT directors—technical buyers who valued detail, stability, and execution.

That positioning made them the default vendor in many large enterprises. But it also trapped them.

The Market Shift

From below, developer-led tools were empowering practitioners to make more buying decisions on their own. From above, cloud hyperscalers were building strong ties with CEOs and CIOs and positioning themselves as strategic partners, not just platforms.

The rules had changed.

Our client wasn’t losing deals on functionality or pricing. They were being written out of the conversation before it even started. Because at the C-level, decisions are shaped by broader priorities—growth, risk, transformation. Not features.

The Challenge

The CRO had a clear mandate. The team needed to engage higher. But reps weren’t ready to operate at that altitude.

They were brilliant with specs. Comfortable with procurement. Trusted by directors. But when it came to CIOs, they lacked fluency. They couldn’t hold their own in strategic conversations that weren’t about technology, but about outcomes.

That’s when they turned to Forge.

The Approach

We didn’t build a playbook. We didn’t run a training. We didn’t simulate a sale.

We built a simulation that forced reps to stop acting like sellers and start thinking like CIOs.

In this immersive experience, reps became the CIO of a national retail chain. They were responsible for modernizing a complex tech stack—consumer apps, backend systems, employee devices—while navigating resource constraints, organizational friction, and shifting business demands.

No pitches. No quotas. No decks.

Just C-level decisions.

The Experience

The simulation unfolded over three rounds, each representing a fiscal year. In each round, participants faced realistic executive dilemmas and had to make tradeoffs:

• Should we prioritize an e-commerce rebuild or double down on fraud prevention?
  
• Do we expand the cloud team or invest in AI-driven inventory management?
  
• What do we do when security flags a marketing tool mid-campaign?
  
  

Participants weren’t judged on bookings or pipeline. Instead, they saw metrics like:

• IT spend as a percentage of revenue
  
• Mean time to respond
  
• Project delivery velocity
  
  

They experienced the same tension real CIOs manage daily:

• Balancing operational stability with innovation
  
• Meeting stakeholder demands with limited resources
  
• Justifying investments to a skeptical CFO
  
  

These were not abstract scenarios. They were grounded in the kinds of decisions CIOs live and breathe—decisions that are invisible to most sellers.

What Changed

One seller summed it up best:

"Now I realize I'm not just competing against our obvious competitors. I'm competing against every other initiative the CIO could fund. Infrastructure upgrades. New hires. Supply chain projects. I need to position our value in that context."

That shift in perspective changed everything.

Post-simulation, reps were more confident and credible in executive settings. They understood how to speak to business priorities, not product features. They stopped asking for time and started earning it.

The company saw measurable results: more in-person CIO meetings, larger deal sizes, stronger executive alignment.

And most importantly, the enablement team didn’t deliver a one-off event. They built an internal capability.

The Bigger Picture

This is what simulation is for. Not performance theater. Not checkbox training. Capability building.

You don’t equip sellers to sell higher by teaching them how to fake fluency. You do it by letting them experience the world their buyers live in.

That’s the Forge philosophy.

You’re not just preparing people to talk about business value. You’re letting them feel the tradeoffs. The pressure. The constraints. The stakes.

That’s what creates transformation. Not passively watching. But actively owning.

If your team needs to operate at a higher altitude, give them a new perspective. Stop scripting the conversation. Let them live it.

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