Should we hire a person or AI?
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Recently, I found myself staring at a ClickUp dashboard wondering something I never expected to ask out loud: should our next hire be a person... or AI? We’ve been jamming recently on this idea and had a big jam session as a team in the last week. This wasn't a theoretical exercise. We’ve been actively weighing candidates for a critical role. It was down to four options:
A part-time contractor who knows us, shows promise, and is hungry to grow.
A dynamic full-time candidate with deep expertise and a network.
A contract veteran with strong operational muscle.
AI agents, integrated with our stack.
What unfolded was one of the most thoughtful, revealing team conversations we've ever had. It wasn’t just about skills. It was about values, velocity, and the kind of company we want to build. We’re really answering a bigger question: What kind of team do we want to build, and what should work even feel like in 2025?
Tools are only as useful as the structure around them
AI agents are crazy powerful. They can automate task assignments, write docs, track OKRs, build functioning prototypes, and integrate with almost every app we use. With the right setup, they can eliminate a large chunk of the manual work that usually slows teams down.
But that power is a trap if your team isn’t aligned on how to use it. We realized that the biggest issue wasn’t tool selection. It was the lack of structure around how we operate: who owns what, when handoffs happen, how projects get scoped, and what “done” actually looks like.
Before we could make AI useful, we had to get clear on our working model.
Teams don’t need roles, they need functions
We started reframing the conversation. Instead of saying "do we need someone in an operational role?" we’re asking:
Who owns the orchestration of complex projects?
Who’s ensuring we communicate clearly with clients?
Who’s connecting dots across projects, people, and systems?
Sometimes, that answer is a person. Sometimes, it’s a combination of people and well-trained AI. And sometimes, it's a temporary contractor with deep systems experience who builds the foundation others can grow on.
That’s when it clicked: we were trying to solve a phase-specific challenge with a permanent solution.
A phased approach to hiring and scaling
I think building a team is a lot like building products/software. Don’t build the final version. Build the next version. Test. Learn. Adjust. Here’s the three-phase model in my head:
Phase 1: Foundation: Stand up core systems and clarify rituals. Use tools like ClickUp (or your tool of choice) to codify how you work. Bring in a contractor if needed to get the bones in place.
Phase 2: Augmented execution: Train your team (and tools) to operate consistently. Blend AI agents with human oversight.
Phase 3: Strategic depth: Once systems and roles are humming, invest in full-time hires who bring relationship-building, intuition, and creativity. That’s when cultural impact become differentiators.
We’re somewhere between phase 1 and 2 now, and we’re embracing that.
Putting this into action
If you’re facing a similar crossroads, here are some things I’ve been chewing on lately that may help you:
Map the work, not the role: What needs to get done? Who or what can do it best?
Stand up your tools, then teach your team: Don’t expect software to solve undefined/inconsistent process.
Use contractors to accelerate systems: Temporary help can set up structures that stick.
Invest in talent that sees around corners: When it’s time for full-time hires, pick people who elevate the team, not just fill a gap.
Think in phases, not permanence: You don't have to solve for the next 5 years. Solve for the next 5 months. We realized we might not need a full-time role yet if we can ramp our existing team and bring on a fractional contractor to support us.
Evaluate candidates by additive value: We started asking: "What can this person do that no tool can?" For our top candidate, it was community reach and synthesis across functions. For the part time contractor, it was trust and trainability.
Use AI as augmentation, not substitution: Our best outcome wasn’t AI or a human. It was AI plus a human who can direct it. We started scoping a contractor who can build the AI agent role, then train the part time contractor to operate it.
Culture is built in the gray moments: The debate itself shaped our values. The transparency, the back-and-forth, the willingness to say "I don’t know" out loud, that’s the culture we want. That’s what matters more than any one hire.
Wrapping up
The future of employee experience isn’t binary. It’s blended. AI won’t replace great employees. But it will expose the gaps in your systems, your structure, and your ways of working. We need humans who can use AI wisely. We need systems that flex for real life. And we need to be honest about what work needs a heart, not just a head.
Your job isn’t to choose between people and AI. It’s to build a blended team that makes both better. We’re betting on both. People first. But powered by systems that make them better.
Onward & upward,
Drew
P.s. If we haven’t met yet, hello! I’m Drew Burdick, Founder and Managing Partner at StealthX. We work with brands to design & build great customer experiences that win. I share ideas weekly through this newsletter & over on the Building Great Experiences podcast. Have a question? Feel free to contact us, I’d love to hear from you.