How AI is Changing Project Management

Height 2.0 and why project management will become invisible

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Hot take: founders should spend 0% of their time on project management.

When I say this to founders they tentatively nod in agreement — they know that startups are chaotic and maintaining an accurate project task list is often impossible but they don’t know a better way.

But what if it took no time at all? Then wouldn’t accurate priority lists and project boards be… actually pretty useful for chaotic startups?

Michael Villar thinks so. He saw the value a single source of truth created for teams after building and launching foundational products at Stripe like Stripe Checkout, Stripe Atlas, and the Stripe iPhone app.

Six years ago he set out to build what became Height — the first autonomous project collaboration tool. During that time he’s raised a Series A led by Redpoint and an earlier round included participation from Lightspeed.

I sat down with him this week to better understand how AI gives us the option to make project management fully automated and “invisible” to humans. I walked away compelled that Height is disrupting the market.

Here’s how project management will change by 2030 👇

How AI is Changing Project Management

The Status Quo

The kanban board was invented over 70 years ago and has been used to manage software projects at least since Microsoft began using it in the early 2000’s. It’s since become part of the status quo for project management, alongside project task lists, standups, and more.

Each component of project management has historically required tedious, manual work that wouldn’t otherwise exist — it’s entirely lacking in automation and takes time away from actually building products or talking to users.

That often doesn’t work for founders. I can’t tell you how many times I’ve tried to set up a project tracking system for my teams over the years, only to be the one to stop keeping up with it myself.

That leads to a world where startups don’t have a single source of truth for information about what’s going on within the company. You can see the problems here — keeping teams on the same page is challenging, onboarding new hires is even harder, and critical information leaves the company if team members do.

But LLMs have, for the first time in over 20 years, created an opportunity to actually rethink project management from first principles — and Height is capturing it.

Autonomous Project Collaboration

The ideal project management tool is invisible and removes all manual work.

In the background, it simply keeps information current and updates your team either automatically or on demand. Your documentation becomes a set of detailed prompts for a system that can then add and glean context within your team’s conversations (and proactively propose solutions or inject reminders).

When you think of classic project management actions like triaging bugs, prioritizing improvements based on customer feedback, scoping sprints by task size and people resources, descoping projects when they are delayed, most of the time, we just apply a manual script we learned about how to do one of these things.

Now imagine having AI apply that script for you. Could these parts of project management be done better and/or faster by AI? In a lot of cases, the answer is yes.

- Michael Villar, Founder & CEO of Height

This allows you and your team to focus on doing high quality work rather than updating kanban boards or sharing standups — your standups will write themselves.

This actually already exists within Height. Standups are auto-generated updates that land in your inbox. You get a roundup of the team’s tasks, even the tasks where they weren’t assigned but jumped in to provide help or feedback to others. You can get a much clearer context on where all projects stand than you would in a 15-minute meeting:

Height makes standups more comprehensive and autonomous

Height’s vision is a lot bigger than standups though. They’ve already launched features that enable their AI to draft release notes, track feedback, deduplicate task lists, and summarize conversations about issues — all automatically.

When I spoke with Michael, he mentioned how knowledge workers typically lose as much as 5 hours each week to tedious, manual project updates. As teams get larger I’d imagine this increases.

Ironically, Height is the first project management tool I’ve come across that actually reduces the amount of time teams need to spend managing projects thanks to the thoughtful way they’re building with LLMs.

Project Management in 2030

To build the future you need to start from first principles — now that LLMs exist and are accessible, what’s the best product and user experience for project management?

Michael said it best when we spoke:

The immediate impulse when building with generative AI seems to be “let’s build a chatbot that can answer users’ questions.” We’re trying to balance when to let the user choose what to ask an AI bot themselves, versus offering them a fully AI-native workflow. We always prefer the latter.

We see a future where humans never manage a project again. That’s the core vision that we’re building Height 2.0 around, and we evaluate our product decisions based on how close they get us to that goal.

In the same way that self-driving cars are autonomous, AI will clear the way for collaboration across teams by taking all that cross-functional friction out of the way.

- Michael Villar, Founder & CEO of Height

Think about it — LLMs have immense knowledge of your team’s localized “world” in any setting. This creates a natural single source of truth.

In Height’s case that includes project management methodologies, millions of open issues and task reports, and definitions of what makes a project successful or not. We’re seeing the emergence of a new type of UX that isn’t intrusive but is integrated into existing workflows.

I’m bullish on this future, especially for founders!

A Disruptive Opportunity

A good product is one thing, but Height also has the right timing and positioning to disrupt the industry.

As the existing incumbents focus on their high-margin and high-revenue customers, the majority of lower-ticket customers get left behind. Their evolving needs aren’t met and Height, as a new entrant, can capture them.

In our conversation, Michael predicted that incumbents would embrace AI but that they’d use it to make modifications to their existing products and workflows — to make them more efficient — rather than rethinking the product experience from the ground up:

What I see a lot of right now is AI being added as separate features of existing products, instead of rethinking what it means to build a product from scratch with AI under the hood. But the transformative AI tools won’t have a divide between what is core product, and what the AI layer is.

In the long term, they should be one and the same, indistinguishable from each other.

Michael Villar, Founder & CEO of Height

This rings true to me (some evidence: OpenAI may be building a physical device to compete with the iPhone) and helps open up an interesting category of opportunities where AI is both a sustaining innovation (as Sam Lessin predicted) and a disruptive one. A better way to think about that — and what Height is doing — is re-creating new markets within existing ones from the ground up.

Why I’m Bullish On Height

I was fully expecting to be more skeptical but I came away from the conversation impressed and more excited about project management than I’ve been… basically ever.

Height 2.0 will get founders to a point where managing task updates or writing project specs will be like sending a fax — once essential, but no longer something we do.

I for one am excited for the end of human-led project management as we know it today.

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