“This Meeting Could’ve Been AI”

Oh, hi 👋 

From CEO memos on AI adoption to Microsoft’s report on the chaos of modern workplace to OpenAI’s enterprise playbook — this week is all about how AI is reshaping the way companies operate from the inside out.

Let’s dive in.

What’s happening:

CEOs from Shopify, Duolingo, Uber, and Fiverr are broadcasting a clear message to their teams and sharing them publicly as well: “AI-first isn’t a buzzword — it’s a requirement.”

Why it matters:

We’re now seeing a seismic shift in leadership expectations. These memos aren’t gentle nudges — they’re full-blown directives to rearchitect how teams work, hire, and justify headcount.

• Shopify: AI usage is now a baseline job expectation.

• Duolingo: Headcount will only be given if a team cannot automate more of their work

• Uber: Learning to use AI agents to code is a “must” within a year.

• Fiverr: AI proficiency is part of hiring and performance reviews.

The hard truth:

The work that used to keep people busy all day — can now be near-instant. Teams are learning the hard way: you can’t just bolt on AI. You have to rewire how the work gets done.

If your ops still rely on 8 people manually moving data between tools and spreadsheets, AI doesn’t optimize it — it makes it obsolete. That demands a different kind of org design.

What we’re seeing at Switchboard:

This new era of AI-first thinking matches what we’re seeing companies coming us to ask for support on. The memo mindset is real, but execution is the gap. Teams are needing clarity on:

• Helping Ops roles & teams refactor and redesign workflows.

• Making sure data and tool integration is ready for AI.

• Integrating AI into processes that are ready for it and helping retool ones that aren’t.

The takeaway:

AI-first isn’t optional anymore. But most businesses aren’t equipped to make the leap alone. The org chart needs a rebuild — and the smartest teams are already reskinning the architecture.

Check out some of the CEO memo’s here:

• Shopify

• Fiverr

• Duolingo

• Uber

• Zapier (not a CEO memo but a good summary of how Zapier has approached making their own company AI-first)

What’s new: OpenAI studied 7 enterprise leaders that are ahead of the curve with AI. Each one turned experiments into impact—streamlining ops, enhancing products, and multiplying output. The takeaway? Early action and fast iteration win.

Why it matters: These are big companies solving big problems—but the playbook applies at any scale. For small and mid-sized businesses, adopting AI early (and intentionally) can unlock efficiency, edge, and growth before competitors catch up.

7 enterprise-tested lessons

1. Start with evaluation:

   Morgan Stanley rigorously tested models before scaling. Result: 98% adoption among advisors, faster research, better client service.

2. Embed AI in your tools and services:

   Indeed personalized job matches using GPT-4o. Uplift: 20% more applications, 13% higher employer success rates.

3. Start now, invest early:

   Klarna’s AI assistant now handles 2/3 of chats. It saved $40M+ in a few months and improved employee adoption across the board.

4. Customize and fine-tune models:

   Lowe’s fine-tuned GPT for search accuracy. Result: +20% tagging accuracy, +60% error detection.

5. Put AI in experts’ hands:

   BBVA launched 2,900+ internal GPTs in 5 months. Legal, Risk, and Ops teams slashed time and improved decisions.

6. Unblock your developers:

   Mercado Libre built “Verdi,” a no-code AI dev platform. Now devs build faster, tag 100x more products, detect fraud, and personalize content at scale.

7. Set bold automation goals:

   OpenAI automated internal customer support. Result: faster replies, fewer repetitive tasks, and better cross-team efficiency.

Go deeper: These wins come from starting small, learning fast, and iterating. OpenAI’s lesson? AI success demands hands-on use, continuous feedback, and bold vision.

Read the full report →

Microsoft’s 2025 Work Trend Index, a global report drawing insights from 31,000 workers and trillions of Microsoft 365 data signals, captures the chaos of the modern workday.

It’s not just about AI. It’s a pulse check on how work actually happens today — and where the cracks are widening.

275 interruptions a day.

That’s how often employees are pinged — every 2 minutes — by Slack, Teams, email, or a last-minute meeting.

Why it matters:

It’s not just digital noise. It’s a sign of workflows that weren’t built to scale. Instead of doing real work, teams are trapped in a constant loop of:

• “Where’s that file?”

• “Is this updated?”

• “Who owns this?”

It’s operational drag — and a red flag for any company trying to grow without rethinking how work flows.

The reality:

• 80% of workers say they’re too maxed out to do their job well.

• 60% of meetings are unscheduled and chaotic.

• PowerPoint edits spike 122% right before meetings — a symptom of reactive work, not planned execution.

🤖 The AI Shift: What Leaders Need to Know

This isn’t about layering AI on top of chaos. It’s about reworking how your business runs — which, as we’ve said earlier in this newsletter, is the real unlock.

Microsoft’s data shows a clear direction:

• AI is becoming digital labor. Agents are being used to expand team capacity and take on repeatable tasks.

• Your team will manage AI — not just use it. Employees will direct and oversee agents like junior staff.

• New roles are emerging. From AI Strategists to Agent Specialists, the org chart is shifting fast.

• The most agile businesses are already ahead. They’re using AI to streamline ops, speed up execution, and reduce the load on their teams.

🧠 What This Means for You

If you’re feeling the pain of endless status checks and bloated meetings — you’re not alone. But fixing it isn’t about another tool or another training. It’s about rethinking your workflow from the ground up.

AI can help — but only if you do the redesign.

This report is a wake-up call. Worth the read if you want to see where the future of work is heading — and how to stay ahead of it.

Read the full report →

Chat soon 👋