Michael Villar Of Height: How AI Is Disrupting Our Industry, and What We Can Do About It

An Interview With Cynthia Corsetti

Don’t try to play catch up with your competitors. Building things just for the sake of feature parity is not a strategy. And that’s more true than ever with AI. There’s no proven playbook yet. Everyone is still figuring it out. Instead, lean on your own strengths and unique insights into your industry and customers.

Artificial Intelligence is no longer the future; it is the present. It’s reshaping landscapes, altering industries, and transforming the way we live and work. With its rapid advancement, AI is causing disruption — for better or worse — in every field imaginable. While it promises efficiency and growth, it also brings challenges and uncertainties that professionals and businesses must navigate. What can one do to pivot if AI is disrupting their industry? As part of this series, we had the pleasure of interviewing Michael Villar.

Michael Villar is the Founder and CEO at Height, a collaborative tool with the mission to automate project management. Before founding Height, Michael also co-founded Kickoff, a productivity company acquired by Stripe in 2013. As an early product designer and fullstack engineer at Stripe, he built products like Stripe Checkout, the iPhone app, and Stripe Atlas. At Height, he leads the global 20 person team and their company strategy.

Thank you so much for joining us in this interview series. Before we dive into our discussion our readers would love to “get to know you” a bit better. Can you share with us the backstory about what brought you to your specific career path?

I’ve been drawn to tech and tech startups since my childhood. Growing up in a small village in Belgium, I was fascinated by the dotcom boom from afar, and all the ways people were creating and selling digital products. At 14 years old, I was already selling skins for online forums, and building other software that I sold to people around the world. By the time I graduated from college, I knew I wanted to build my own product and company. So I co-founded Kickoff, a productivity startup, with a good friend, which was acquired by Stripe in 2013, and that brought me to San Francisco.

Joining Stripe gave me a whole new perspective on the mechanics of building a business online. Stripe’s mission to abstract away the pain of setting up payment processing so people could focus on actually building their businesses really resonated with me. Likewise, my experience there really set me up with an understanding of the fundamentals of running a successful company.

After several years at Stripe, I was ready to apply all this experience directly to building a business of my own again. To sell my own product, set the strategy, create something that helps elevate other builders too. And that’s what led me back to founding my second startup, Height.

People are often surprised that Height is in a similar space as my first startup Kickoff was, but the truth is that I love well-built products, and much of the talent of our generation has focused on consumer apps, shortchanging the B2B work tools we use everyday. Companies like Slack, GitHub, and Figma have helped change this, and I’m excited to be part of the movement to bring design sensibilities to business tools.

What do you think makes your company stand out? Can you share a story?

At Height, we’re building the world’s first autonomous project collaboration tool. Our team is comprised of experienced product builders coming from companies like Apple, Microsoft, Instagram, and we draw directly on our own familiarity with the space. Too much of our time historically has been spent on the many required tasks to keep a project on track — triage, backlog refinement, status updates, etc.

What makes us stand out is that we’re building a project management tool with AI at its core, not as an add-on or tacked on feature. Our goal is to actually take on all of the tedious project management legwork that is essential to the project’s success. Instead of just trying to make these chores easier or faster for you to do, we’re removing them from your plate so you can focus on the impactful work

An autonomous project management tool removes chores from your plate and handles them on autopilot. What I’m getting at is, the more you can offload the drudgery to Height, the more you can spend time on building something your customers love.

You are a successful business leader. Which three character traits do you think were most instrumental to your success? Can you please share a story or example for each?

Without a doubt, resilience has been key throughout my entire journey, especially as a solo founder. The first year after starting a new venture requires a lot self-motivation, pushing past any doubts, almost to the point of self-delusion.

As Height has grown, another skill I rely on constantly is a problem-solving oriented approach. When founding a company, you’re constantly facing new-to-you challenges, like managing payroll across many countries, setting up growth flywheels, or learning how to evaluate and hire leaders in other disciplines. And this is all of course in addition to making the strategic decisions required to build a successful product. Being able to problem-solve on the fly can often feel like the make-or-break ability as an early stage business owner.

And since I’ve always been drawn to extremely product-centric companies, being able to flex between engineering, design, and product roles has been a huge asset. At Stripe, I was both a fullstack engineer and a designer, and combined with my experience as a product owner at my previous startup, I’m now able to context-switch and pitch in wherever is most valuable. I predict we’ll be seeing similarly collapsed talent stacks a lot more now with AI helping builders expand their skill repertoire and leverage.

Let’s now move to the main point of our discussion about AI. Can you explain how AI is disrupting your industry? Is this disruption hurting or helping your bottom line?

LLMs are absolutely changing what’s possible, and within the productivity space, it’s no different. While the current trend within our space has been to focus on chatbots and tentative AI-powered features to test the waters, I’ve been fundamentally rethinking what tasks are mission-critical for humans to be doing vs ones that are ripe for automation.

One example top of mind for me is related to how product teams are always staving off decision fatigue. Product owners not only have to figure out what to build and how to build it, but also think through a million other micro-decisions like “How do I triage this bug?” or “How do I declutter my 300-ticket backlog?” Instead of trying to build tools that enable them to make these calls faster or more efficiently, those decisions can be offloaded to AI reasoning.

Another interesting illustration of what’s now possible: imagine a customer sends you a screen recording of a bug. AI could analyze that video, identify the issue, convert it into a detailed bug report, and even triage it based on severity and urgency to help the on-call engineer know if it’s high-priority. All of these separate steps are currently eating up a significant amount of your colleagues’ bandwidth. With the advent of powerful multi-modal AI models, we now have a pathway to a future where all this work can be prepared for product managers.

This is the future we’re building towards: one in which teams can invest more of their energy into strategic initiatives that drive the bottom line.

Which specific AI technology has had the most significant impact on your industry?

Large Language Models (LLMs), without question. Take GPT-4, for example, trained on a staggering 1.76 trillion parameters, it opens up possibilities for vector embeddings, in any knowledge software, at a scale we’ve never seen before. It transforms the core intelligence layer on which products are built.

Today, these larger, “generalist” models are in the spotlight, and rightly so. They have the broad knowledge base and versatility that allows them to be applied to all kinds of contexts.

But looking down the road, I can see the shift towards smaller, more domain-specific models. They have much more tailored knowledge for each use case, which could mean higher quality output. Plus, they require less compute, so they’re faster and cheaper to run. That’s the direction OpenAI, Microsoft, and Google seem to be heading in already and I’m keeping a close eye on the latest developments.

Can you share a pivotal moment when you recognized the profound impact AI would have on your sector?

So, I love cars and racetrack driving (there’s a reason the Porsche 911 has a tiny cameo on our Vision page!). But the first time I rode as a passenger in a fully autonomous car, in Waymo’s fleet, I was floored. The promise of autonomous driving has been dangled before us for over a decade, and like most people, I’d grown skeptical of what was going to be possible within the next. And like probably most founders, it’s also important to me to feel in control. However, that very first ride changed my mind and stuck with me because it felt like the future was here. I was able to entrust the driving decisions to the car, freeing up my mind to think about all the other things that occupy mindshare day to day.

This, by the way, is also why I call what we’re doing “autonomous project management” — I want to bring that exact same feeling of entrusting the heavy lifting of day-to-day project management. If we can take something as complex, with as many moving pieces, risks and lives at stake, as driving and remove humans from the loop, project management should be infinitely possible.

How are you preparing your workforce for the integration of AI, and what skills do you believe will be most valuable in an AI-enhanced future?

Defining clear prompts is one of the most obvious for product builders, at least in the near future. How well you communicate with AI is directly proportional to the performance and seamless end-customer experience you can expect of it.

At the same time, as the use cases we apply AI to grow more complex, designing good prompts will be table stakes. We’ll likely see more focus on building a portfolio of different prompting techniques, devising reliable strategies to test and optimize the outputs, and being able to design prompts that work across different AI modalities.

What are the biggest challenges in upskilling your workforce for an AI-centric future?

One of my top priorities is getting my whole team familiar with the potential of AI. Engineering, design, marketing, support — we encourage everyone at Height to experiment with AI and use it day-to-day. Our offsite hackathons have been a great start to get everyone to build with and think through the possibilities of AI.

It’s not enough for only the head of the company to be testing and following the latest developments. If you’re building with AI, your whole team needs to be constantly asking themselves, “Is this something that could be done well with AI?” Using AI tools themselves day-to-day builds an understanding of what’s possible and helps everyone be empowered to dream of how your company can benefit from what’s now possible.

I’m really stressing this point because if you’re relying only on yourself to stay up-to-date with the latest of AI, you become a single point of failure. A resilient company depends on multiple people experimenting and actively questioning and rethinking company strategy based on the breakneck speed of AI development.

What ethical considerations does AI introduce into your industry, and how are you tackling these concerns?

Building AI into Height 2.0 has definitely been an eye-opener. It’s putting our guiding principles to the test in all kinds of new ways. At the top of the list is establishing a quality threshold for the AI output we accept and will surface to our end users. Content produced by AI can be a bit of a wild card, so having solid, system-wide quality standards is key to build trust with users. We’re also involving people outside of just engineering when writing our underlying prompts, to expand the experience and backgrounds that feed AI experiences.

We’re also not here to flood our users with low-value AI-generated text. That’s not helpful. If people are bombarded with a wall of text without confidence in its accuracy, they can easily lose faith in the product. For example, if AI credits something to a teammate, we need to be fully confident that the person actually said it. There’s no room for hallucinations when people’s social credibility are involved.

What are your “Five Things You Need To Do, If AI Is Disrupting Your Industry”?

1. Look at AI’s impact on your space right now and assess if it’s signaling a long-term disruption. Is it just another shiny hype or could it actually make your business irrelevant if you don’t adopt it and immediately shift your company strategy?

2. Go on a discovery journey to understand how AI actually works, hands on. Take a few different AI-powered tools out for a test drive, and encourage your team to do the same. Experiment with prompting in the OpenAI Playground. Look beyond text generation — think multimodal. Try image, video, and audio models. This will help you uncover the unique competitive edge you can capitalize on if you pivot your strategy towards AI.

3. Study the early AI disruptors in your space. Are they additive to your product offering or replacing it entirely? There’s a lot of room for partnerships and integrations. Unless you’re building full-on AI models, there’s no sense in competing directly with ChatGPT or Claude, for example. You can carve out a unique market position by strategically integrating AI capabilities, instead of fighting them. An added bonus is you get to leverage the product velocity of these AI partners to accelerate your own product, without additional effort on your part.

4. Don’t try to play catch up with your competitors. Building things just for the sake of feature parity is not a strategy. And that’s more true than ever with AI. There’s no proven playbook yet. Everyone is still figuring it out. Instead, lean on your own strengths and unique insights into your industry and customers.

5. Decide if you’re going all in on AI or not at all. Don’t just put one foot in. I see a lot of tepid AI “add-ons” right now, rather than products built from the ground up around AI. But the transformative AI tools won’t have a divide between what is core product, and what is the AI layer. In the long term, they should be intrinsically linked, indistinguishable from each other.

What are the most common misconceptions about AI within your industry, and how do you address them?

When people hear “generative AI”, their mind goes straight to writing, summarizing, and extracting text. And we’ve already seen some of these applications in a project context: Notion’s autofill tables, ClickUp’s writing assistant, Asana’s smart answers.

However, I think many people are stuck in a tunnel vision mindset of what’s possible. LLMs are not just writers, translators, or summarizers. They can provide so much more. For me, AI reasoning is what will really take this generation of products to the next level. The room for innovation is vast, and as founders, we should not confine ourselves to chatbots, text generation, and what we’ve already seen.

Can you please give us your favorite “Life Lesson Quote”? Do you have a story about how that was relevant in your life?

Run lean. I’m paraphrasing Elad Gil here, but essentially as an early-stage startup, stay as small as possible and hire the absolute minimum. Pour your energy into building a great product, fast, with minimal overhead. That philosophy is at the center of Height, both as a company and a product.

And staying lean takes on added relevance with AI. Automating peripheral tasks to AI frees up everyone’s bandwidth to achieve more and flex to where they’re most needed, so smaller teams will be able to accomplish bigger feats.

Off-topic, but I’m curious. As someone steering the ship, what thoughts or concerns often keep you awake at night? How do those thoughts influence your daily decision-making process?

With the speed at which AI is evolving, we have to be extremely focused about what we build with it. It’s almost like you blink, and there’s a new innovation that gets the whole industry buzzing.

Our backlog has hundreds of ideas, but we need to focus on building the most impactful ones, that create the most value for our customers. The tricky part though is what’s possible to build could change every month depending on the latest AI developments. So when do you stick to your plans and when do you pivot? It’s a fine line to walk.

For me personally, I’m always thinking about achieving that balance between moving fast and staying focused. Sometimes we need to change trajectories, but there has to be a strong reason for it, not just to chase the latest shiny AI use case. Having a strong product vision to lean back on during these judgement calls makes these decisions approachable.

You are a person of great influence. If you could start a movement that would bring the most amount of good to the most amount of people, what would that be? You never know what your idea can trigger. 🙂

I want to contribute to building a future where we can do more with less. This has been the promise of technology all along, and you can see that potential has been realized in pieces of personal tech like the dishwasher, Roomba, or the SNOO. All these innovations that help us make the most of our personal time.

But work tools have yet to fulfill that same promise — they still demand our attention, energy, and constant upkeep. We’re working more, not less. That’s where I see a huge opportunity to refocus work tech on helping us achieve our most significant goals, using the fewest resources possible. AI innovations are an opportunity to step back and rethink the way we work, and the way we build.

I think that’s more imperative than ever, not just for our work lives, but also when we look at global challenges like climate change, for example, that call on us to get creative with how we use our limited resources and prioritize sustainability.

How can our readers further follow you online?

@michaelvillar on Twitter/X and Threads and my Substack newsletter.

And you can sign up for early access to Height 2.0 here.

Thank you for the time you spent sharing these fantastic insights. We wish you only continued success in your great work!

About the Interviewer: Cynthia Corsetti is an esteemed executive coach with over two decades in corporate leadership and 11 years in executive coaching. Author of the upcoming book, “Dark Drivers,” she guides high-performing professionals and Fortune 500 firms to recognize and manage underlying influences affecting their leadership. Beyond individual coaching, Cynthia offers a 6-month executive transition program and partners with organizations to nurture the next wave of leadership excellence.