AI is Breaking Department Silos: Moving from Org Charts to Work Charts

Hello go-to-market leaders, strategists, and innovators! 👋 Thank you for dropping by to learn practical AI applications and gain strategic insights to help you grow your business and elevate your team's strategic value.

Quick Take

AI is changing how teams work together. It’s moving us from strict department lines to simple, flexible ways to get work done.

Enter work charts.

What’s different?

• Org charts = who knows what (departments + roles)
• Work charts = what needs doing (jobs-to-be-done + workflows)

In this edition, I’ll share real-world examples and proven results from companies already starting to work this way and how you can take the first steps.

The shift:

• AI breaks down traditional silos by making expertise available on demand.
• Forward-thinking companies organize around workflows, not functions.
• Humans + AI systems work side by side.
• Rising customer expectations + economic pressure accelerate this.

Start with one cross-functional workflow. Prove value. Expand.

While my work often focuses on go-to-market teams, these concepts apply across all functions and can scale throughout the entire company.

The shift:

• AI breaks down traditional silos by making expertise available on demand.
• Forward-thinking companies organize around workflows, not functions.
• Humans + AI systems work side by side.
• Rising customer expectations + economic pressure accelerate this.

Start with one cross-functional workflow. Prove value. Expand.

While my work often focuses on go-to-market teams, these concepts apply across all functions and can scale throughout the entire company.

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The Shift Already Happening

If you've read my previous newsletters, you've seen how AI is changing go-to-market teams. In "AI Is Redefining GTM Jobs," we explored how teams move through three phases: using AI as tools, guiding AI as teammates, and orchestrating AI systems.

The walls between departments are blurring as:

• AI teammates make expertise available across traditional boundaries
• Customer workflows run with fewer handoffs and stops
• The gap between "who knows what" and "what needs to be done" shrinks

This marks the beginning of a new way to organize teams.

In "Human-AI Org Transformation Playbook," we examined how a lean marketing team grew to include 25 humans and 20 AI teammates working side by side.

From Org Charts to Work Charts: The Next Step

We can see a practical shift in how organizations will structure themselves:

This approach aligns with trends we're seeing across industries. The Microsoft 2025 Work Trend Index Report offers a similar model. They note that "teams form around goals, not functions, with AI helping employees do more and work faster."

Ethan Mollick, Associate Professor at the Wharton School, recently shared insights from a Harvard study with P&G professionals. Cross-functional teams working with AI experienced an interesting finding:

"You stop caring as much about the normal boundaries of your job."

When specialists from different functions used AI, the lines between expertise areas nearly disappeared. Traditional silos broke down as AI helped people think beyond their specialized training.

Leaders are experiencing this firsthand. Scott Braun , CMO of SimpliSafe, shares:

"When we started with AI at SimpliSafe, honestly, we weren't quite sure how it could help us at scale. With the help of Liza Adams during a strategic AI workshop where she inspired us with what's possible with various applied AI use cases, we quickly realized the real power wasn't in just making our old processes more efficient.

We can get the most out of it when we use it as a teammate, as a thought partner, and to connect dots across functions in our org. It was a wake-up call."

Where We Are Today: Reality Check

While work charts show where we're heading, most companies are at earlier stages:

The AI Work Chart Maturity Model presents a staged and simplified view of how organizations are evolving in the AI era. Your company’s path may look different based on industry, maturity, and structure.

Stage 1: Traditional Org + AI Tools

Most organizations currently work here, with individual AI usage within functional silos. Teams use AI separately with limited sharing across departments.

Stage 2: Traditional Org + AI Teammates

Forward-thinking companies work at this level, with defined AI teammates working alongside humans in departments. AI teammates have clear roles and help improve team output within traditional structures. While organizational silos still exist, AI augments individual and team productivity dramatically.

In working with the Dice marketing team, we successfully transitioned to Stage 2 by embedding structured AI teammates into their existing organization. What started as a lean team evolved into a 45-member powerhouse with 25 humans and 20 AI teammates working side by side.

That was in January 2025. Today (May 2025), they have 63 AI teammates. And they anticipate having more than 100 by this summer.

The results:

• 50–75% faster content creation with higher quality
• 98% accuracy in lead qualification
• 35% improvement in campaign performance

Dice built their AI teammates using ChatGPT Custom GPTs and Claude Projects to support specific tasks. But you can also use Gemini Gems, Copilot GPTs, or Glean Apps.

While each company’s structure varies, this diagram shows a conceptual example of how marketing teams can pair human expertise with assigned AI teammates to enhance productivity and reduce repetitive tasks.

AI teammates take on well-defined tasks (like data analysis, content generation, compliance checking), guided and maintained responsibly by human team members.

The Dice marketing team, led by Carol-Lyn Jardine, has since become a trailblazer for the company, conducting AI workshops and mentoring other departments like Sales and Customer Success. They are now beginning to explore cross-functional AI workflows—an early move toward Stage 3 of the AI Work Chart Maturity Model.

Stage 3: Connected Workflows

Pioneers explore this stage, creating workflows where AI connects previously separate processes. Cross-functional workflows form with AI serving as the link between departments. AI enables smoother handoffs, faster information flow, and more consistent customer experiences across teams.

Cin7 offers a real-world example of a company with some workflows operating at Stage 3 of the AI Work Chart Maturity Model.

Sean McCaffrey , Senior Director of Marketing Strategy and Operations at Cin7, shares:

"When we first used AI to identify our most engaged accounts, it opened the door to smarter marketing. Now, we’re going further.

We’re using AI-powered SDR outreach to follow up on demo requests and post-event engagement—personalized at scale on behalf of our human sales reps. Each message adapts based on CRM data, industry, and what we know from their website visits. We’re sharing relevant customer stories and speaking directly to pain points we’ve seen in similar businesses.

We're also sharing what we learn from sales conversations with customer success for better onboarding.

What began as one focused solution has become a connected workflow.

This level of scale and precision simply wasn’t possible with manual email sends. AI isn’t just making our process more efficient—it’s helping us meet prospects where they are, with what they care about."

Their results speak for themselves:

• 78% open rate + 20% booked meetings for demo requests
• 92% open rate + 3.5% booked meetings for event follow-up

AI has moved from simply enhancing tasks to orchestrating cross-functional work at Cin7.

Stage 4: Work Chart Organization

The full work chart model takes shape when companies organize primarily around jobs to be done rather than departments. This creates a new way to structure teams.

Most companies are in Stage 1 or early Stage 2. The full work chart model (Stage 4) exists in pieces but not yet fully in most organizations. However, this change moves faster than many expect.

The Stage 4 work chart structure aligns with my automation vs. augmentation framework above that I sketched out over a year ago. I originally drew this for marketing but this can be applied across organizations. It was a hypothesis back then. Now we're seeing evidence that this is becoming reality.

In this model, experts (both human and AI) come together to support specific workflows—some joining for short periods (ephemeral) while others stay involved longer (everlasting).

Three Forces Speeding Up This Change

Why is this organizational shift happening now? Three key forces come together:

1. Economic Pressure

Microsoft found that 53% of leaders say productivity must increase, while 80% of workers report lacking time and energy. Their data shows employees face interruptions every 2 minutes—275 times daily. Traditional structures can't solve this productivity gap.

2. AI Advancement

AI is growing from simple tools to systems that can coordinate work. OpenAI describes five levels of AI growth:

1. Chatbot - Answers questions with information.
2. Reasoner - Asks questions and adapts to context.
3. Agent - Takes action, plans, and completes tasks autonomously.
4. Innovator - Uncovers insights and proposes new ideas independently.
5. Organization - Works and learns across many functions with minimal human input.

We're currently between levels 2 and 3, with levels 4-5 on the horizon. As AI reaches these higher levels, work charts become a more natural way to organize.

3. Higher Customer Expectations

Customers don't care about internal departments. They want seamless experiences. 

Jacob Warwick , CEO of ThinkWarwick Global and an executive coach explains:

"Top leaders no longer hide behind department lines. The best are business leaders first, functional leaders second. They see problems and collaborate to fix them—even if it means funding another team's solution.

AI exposes exactly where customers get frustrated and leave. Customers don't care about your org chart. They leave when they hit walls between teams. Period. Top leaders must do the same or quickly become irrelevant or replaced. "

A Simple Template to Begin the Change

Here's a practical approach to move toward work chart organization:

This approach lets you start the change without disrupting your entire organization. Begin small, show value, and grow what works.

Your Next Steps

The move from org charts to work charts happens step by step but has already begun. Companies that see this coming can make choices today that support this change.

Here’s how to get started:

1. Map your key workflows across department lines
2. Find your worst handoff points
3. Create one cross-team test with shared AI support

Small steps in this direction lead to significant gains in customer experience, team effectiveness, and company speed. While I've focused on go-to-market teams, these concepts apply across HR, finance, product, engineering, and other functions.

This shift aligns perfectly with what I covered in my "AI is Raising Customer Expectations" newsletter. As buyers increasingly demand seamless experiences, companies need unified workflows that connect insights across the entire customer journey—exactly what work charts enable.

As the Microsoft 2025 Work Trend Index notes: "We are entering a new reality—one in which AI can reason and solve problems in remarkable ways... A new organizational blueprint is emerging, one that blends machine intelligence with human judgment, building systems that are AI-operated but human-led."

The move from org charts to work charts has already begun. The companies that embrace this shift today will have a massive competitive edge when AI-driven organizational design becomes the standard, not the exception. Where is your organization on this journey?

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