Unless you’ve been dodging your board entirely, they’ve already asked you, “What’s your AI strategy?” And they’re not wrong to ask. It doesn’t matter if you’re a software company, a pizza chain, or a manufacturer of doorknobs, everyone needs to have a plan for AI.
The pessimist will say AI is overhyped. The optimist hopes their business can carry on unchanged. But the best founders? They adjust their sails. They know the market is changing quickly and they’re building a strategy to harness it before they’re left behind.
But what does that actually mean? Are you supposed to roll out chatbots? Automate everything? Retrain your team overnight to become AI experts? Most startups spin their wheels on vague initiatives that look like progress but deliver nothing.
The reality is that AI training only works if it’s tied to a clear goal. Start with a simple question: What are you actually trying to achieve? As with all projects, start with the end in mind. Ask what you want to be true as a result of this work, and build your strategy from there.
- Teach concepts if your team needs to understand what AI is and how it impacts their work.
- Focus on efficiency if you’re trying to help people use AI to work smarter and faster.
- Change the road map if AI will fundamentally alter how you build products.
No Awareness Means No Credibility
Your team doesn’t need to know how to build a neural network, but they do need to understand enough about AI to avoid sounding like amateurs. Awareness isn’t just about sounding smart in meetings; it’s about making sure your team can connect AI’s evolution to the decisions they make every day and protect your company from irrelevance.
Why does this matter? Startups don’t operate in a bubble. Whether it’s sales flagging a shift in buyer behavior, engineering designing a new feature, or customer success navigating tough conversations, the best opportunities emerge when your team can see how AI fits into the broader landscape.
Think about sales reps hyping AI features they don’t understand or engineers investing weeks in tools without realizing that the latest Anthropic release makes their work irrelevant. Awareness gives your team the context to ask the right questions, prioritize the right problems, and avoid wasting time on irrelevant ideas.
AI isn’t something you can delegate to a single team or phase into your strategy later. If you’re waiting for a ‘perfect moment’ to embrace AI, that moment was last year. Even if it isn’t core to your business, it’s core to the future your business will operate in. Leaders who fail to build shared awareness across their teams aren’t just missing opportunities, they’re actively creating blind spots that will inevitably lead to bad decisions.
Awareness doesn’t just drive smarter internal decisions, it protects your external credibility. Investors and customers aren’t testing your ability to say ‘AI’ in a sentence. They’re asking if your team knows how this seismic shift will reshape your market and your product. If your answer isn’t convincing, they’ll assume your strategy isn’t either.
Efficiency Is About Getting More from Less
If awareness builds understanding, efficiency delivers ROI. The fastest way to get value from AI is by teaching your team how to use it to work smarter.
One of our startups, WorkHelix, is a pioneer in taking a task-based approach to work, and it’s reframed how I think about jobs entirely. “Jobs” are just bundles of tasks, and AI doesn’t disrupt entire roles; it disrupts workflows. Instead of asking, “How will AI change my customer success team?,” ask how it will change ticket handling, escalations, and customer outreach. What can AI accelerate, automate, or eliminate?
There’s no cookie-cutter approach here. AI opportunities will look different across functions. For engineering, it might mean rolling out GitHub Copilot to speed up coding. For sales, it might mean training reps to write prompts that generate emails people actually open. For customer success, it could mean using AI to triage tickets and cut response times in half.
And prompts? They’re the new literacy. Teaching your team to write sharp, targeted inputs is like teaching them to ask the right questions in a strategy session. A lazy prompt gets lazy results. A smart, specific prompt can unlock transformative work.
AI efficiency isn’t about replacing people. It’s about removing friction and freeing your team to focus on higher-value work.
Your Roadmap Won’t Rewrite Itself
If your product is going to have an AI component (hint: it will), your team needs to think beyond features. AI changes how you solve problems, deliver value, and avoid becoming obsolete.
Here’s the existential product question every founder needs to ask: Is AI going to make my product irrelevant?
As models improve, some products and features will get left behind. If your strategy is just about staying ahead of today’s models, you’re already losing. Instead, your roadmap needs to align with AI’s trajectory. Build features that get better as the underlying models improve, not features that get wiped out by them.
Ask yourself: “How does this feature hold up as models improve? What’s its long-term defensibility?” If you can’t answer confidently, rebuild your roadmap.
Founders who roll their eyes at AI strategies are ignoring history. Mobile in the 2000s and the web in the ’90s were seismic shifts too. AI will follow the same pattern: early hype, overblown promises, and eventual transformation. If you’re not engaging with AI, you’re not just opting out. You’re handing the win to your competitors.
Map Your AI Goals by Function
Once you’ve clarified your why, the question becomes, “For whom?” The needs of your engineering team are wildly different from those of sales or customer success. Use a matrix to align each function’s unique needs with one of the three AI goals: concepts, efficiency, or roadmap.
Here’s how to put this into practice:
For awareness: Identify the gaps. Does sales need to explain AI features without sounding like they’re bluffing? Does engineering need to understand where AI models are heading? Awareness is about enabling smarter conversations and better decisions.
For efficiency: Focus on the bottlenecks. What slow, repetitive tasks are holding teams back? Look for workflows like ticket triaging, email generation, or code suggestions.
For roadmap: Think long-term. Ask how AI will reshape demand, where you can leap ahead as models improve, and which offerings risk obsolescence.
Turn this matrix into action. Use a heat map to evaluate opportunities by effort and impact. High-effort, low-impact? Deprioritize. Low-effort, high-impact? Make those your first experiments. This exercise forces you to build a prioritized list and tell you where to begin experimenting without unnecessary distraction.
The Best Founders Have Specific Plans
Your board isn’t asking about AI because they’re curious, they’re asking because they’re worried. They want to know if you’re ready to navigate the biggest shift in decades.
The best founders don’t drown in buzzwords or wing it. They build a plan, even if AI isn’t their core business. They break it down: What’s the goal? Who needs what? Where do we start?
AI isn’t just a feature, it’s the wind changing direction. Adjust your sails.
*Written with help from three AI systems:
- Circleback to record a discussion.
- WisprFlow to allow me to speak my thoughts and capture them faster than I could type.
- ChatGPT to organize and structure my thoughts.