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AI Wants In, Can Your Systems Handle It?
Mary Meeker says AI is here. Notion says most teams aren’t ready. We say mid-market execs have the edge — if they rethink the wiring.

Hi!
We’re back this week summarizing Mary Meeker’s 340-page report on AI in business and some cool announcements from OpenAI on integrating your existing systems more easily with AI.
1. AI Has Gone Mainstream — Now What?
Mary Meeker is back with her iconic trend report — and this time it’s all AI.
Yes, it’s 340 pages. No, you don’t have to read it. We did that for you.
Why it matters:
AI is no longer a "tech initiative" — it’s the new operating layer for business. The report outlines a dramatic realignment in talent, tools, and strategy. The takeaways? Small and mid-market businesses are perfectly positioned to leapfrog slower-moving giants — if they act with clarity and intent.
🧠 Top insights for your org:
Talent is shifting fast: AI-related IT job postings are up +448% since 2018. Those not evolving with AI are being left behind.
Workflows are transforming: Agents, copilots, and ambient tools are already taking over repetitive work — from documentation to customer service.
AI is a C-suite priority: It’s now mentioned by over 50% of S&P 500 CEOs on earnings calls. Mid-market execs can’t afford to ignore it.
The focus has flipped: AI isn’t just about cost savings anymore. It’s driving growth, sales productivity, and customer experience.
💡 How to think about it:
Reframe productivity:
What if 20% of your team's time could be refocused on strategic work by offloading admin with AI?Upskill by doing:
Start AI literacy sprints inside your org. Everyone should know how to prompt, automate, and evaluate — not just your IT lead.Redesign the employee experience:
Workers expect AI support. Integrate AI into onboarding, training, and daily workflows — not just in tools, but in mindset.Be revenue-minded:
The best AI use cases aren't hidden. They’re wherever you have friction in sales, service, or insight generation. Go there first.
📈 The bottom line:
AI is a multiplier — for good or bad. It will amplify whatever foundation your business is built on. Now is the time to tune it for growth.
2. Connectors galore!
What happened: OpenAI dropped a major update: ChatGPT now connects directly to the tools your team already uses — Google Drive, Calendar, Mail, Slack, HubSpot, and more.

Why it matters: Mid-market teams now get real-time, context-rich AI support across their existing tech stack. Instead of siloed chatbots, ChatGPT becomes a true work assistant — digging into files, parsing past meetings, surfacing priorities, and citing its sources.
Search across Google Drive, Slack, and Outlook in one prompt.
Pull up docs, links, and meeting notes directly in ChatGPT.
Record meetings, transcribe them, and summarize with follow-ups.
It’s the beginning of AI as the ultimate cross-platform operator — with your own data as fuel.
My Experience 💬
I connected ChatGPT to my Google Calendar, Drive, and Gmail last night. Then I asked it:
"Create a report on project milestones from our AI rollout."
Nine minutes later, I had:
A week-by-week summary of all key events
Direct links to the emails, meetings, and folders
A shockingly accurate project overview
It was like having an AI chief of staff that knows where everything lives and actually backs it up.
The big picture: Every tool we use is becoming AI-enhanced. The more context and connections we give these models, the more useful and precise they become. This isn’t about replacing workflows — it’s about supercharging them.
3. Notion: “Is Your Company AI Ready?”
Everyone wants AI. Few are truly ready.
Why it matters:
Notion surveyed 1,000+ execs and uncovered the top blocker to AI adoption: integrating it into existing systems. Think: incompatible workflows, strained resources, messy data, and a lack of trust.

📉 The friction:
Teams are jumping between tools just to get work done
AI adoption is often slowed by manual processes and tool fragmentation
Resource and trust issues hold back real progress

📈 What’s driving interest?
57% of leaders want AI to boost productivity
44% are actively investing in AI-supported workflows
They’re craving less friction, not more features

💡 Why this hits home for SMBs:
Switchboard sees this daily—leaders are excited about AI but don’t know how to make it real. What’s missing? A clear AI strategy, integration plan, and roadmap.
🔧 What to do next:
Audit your systems for AI readiness
Start small: Choose tools that embed AI, not tack it on
Build a roadmap aligned to real pain points—not hype
📖 Post of the Week
I love this AI-inspired idea
Friends had a baby shower and this game was a HIT.
They generated 6 AI babies. Only 1 was a combo of the couple. The other 5 were 1 partner + an A-list celebrity.
Those who guessed right were added to a text chat that would be first to get pics of the real baby when born!
— Steph Smith (@stephsmithio)
6:25 PM • Jun 1, 2025
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