How Slack's Sales Team Could Beat the "It's Free" Objection with AI

NOTE: This is a hypothetical case study exploring how Slack's enterprise sales team could leverage DealoAgent.AI. While Slack and its market challenges are real, this scenario is imagined to illustrate DealoAgent's capabilities.

Slack defined the modern collaboration era. But today, they face a formidable existential threat: Microsoft Teams. For many enterprise buyers, the conversation isn't about features or delight; it's about consolidation. CFOs look at their Microsoft 365 subscription and ask, "Why are we paying for Slack when Teams is included for free?" It is the ultimate "Good Enough" vs. "Best in Class" battle.

The Challenge: The CFO's Veto

Meet Alex, an Enterprise Account Executive at Slack. He's managing a renewal for a large retail logistics company. The deal is worth $150k/year. The engineering and product teams love Slack. They live in it. But the new CFO is on a cost-cutting mission.

Alex gets the dreaded email: "We've decided to consolidate on Microsoft Teams to reduce overhead. Please cancel our renewal." Alex knows this is a mistake—he knows the engineering team will revolt and productivity will tank. But he doesn't have the hard data to prove it, and he doesn't know who inside the company is willing to fight for him.

I know the developers hate Teams. I know their Jira workflows will break. But the CFO only sees the $0 price tag. I need to prove that 'free' is actually expensive, but I don't have time to interview 500 users to build a business case.

Enter DealoAgent: Building the Defense

In this hypothetical scenario, Slack uses DealoAgent to turn their sales process into an intelligence operation. DealoAgent connects to Alex's inbox, calendar, and CRM to analyze every interaction he's ever had with this account.

1. Identifying the Hidden Champions

Alex asks DealoAgent: *"Who at RetailLogistics cares most about our integrations?"*

DealoAgent scans two years of emails and support tickets. It surfaces three names Alex had overlooked:

• **Sarah (DevOps Lead)**: Emailed 6 months ago about the PagerDuty integration latency.
• **Marcus (Product VP)**: Replied to a newsletter about the new Workflow Builder.
• **Jen (IT Admin)**: Asked about Enterprise Key Management (EKM) specifically for Slack.

These are his champions. They have skin in the game. DealoAgent drafts personalized emails to each of them: "Hi Sarah, I know your team relies heavily on the PagerDuty integration. We're facing pressure to move to Teams, which doesn't support the custom workflows you built. Would you be open to a 10-min call to discuss the impact on your on-call rotation?"

2. Quantifying the "Switching Cost"

The CFO argues that Teams is free. Alex needs to prove that *switching* is expensive. DealoAgent analyzes the account's technical footprint based on past technical reviews and support queries.

**DealoAgent Insight**: "This account has 42 active custom workflows and 15 critical integrations (Jira, GitHub, PagerDuty, Datadog). Based on industry averages, rebuilding these in Teams would require approximately 300 engineering hours."

Now Alex has a number. 300 hours x $150/hr = $45,000 in immediate migration costs, plus the risk of downtime.

3. The CFO-Ready Business Case

DealoAgent doesn't just give Alex the data; it helps him present it. It drafts a "Cost of Change" analysis document for the CFO, highlighting:

Alex sends this to the CFO, copying Sarah (DevOps) and Marcus (Product). The "Free" argument suddenly looks very expensive.

The Impact

Conclusion

When you're selling against "free," you can't compete on price. You have to compete on value. But value is invisible unless you have the data to prove it. DealoAgent gives Slack's sales team the X-ray vision to see where that value lives—in the integrations, the workflows, and the champions—and the tools to turn that insight into a winning defense.