Lessons from May Habib

As the co-founder and CEO of Writer, a full-stack generative AI platform, May Habib has emerged as a prominent voice in the tech industry. Her journey as a multi-time founder and her insights on artificial intelligence, entrepreneurship, and the future of work offer valuable lessons for leaders and innovators.

On the Transformative Power and Reality of AI

On the potential of AI: "We can have a future where AI takes dignity away from a lot of people. Or, we can have a future where AI enables a lot more progress, access, and prosperity. We're working like hell for the latter." [1]
On AI's impact on work: "The future is work where you get to do the work you want and let AI do the rest." [2]
On the current state of AI adoption: "Despite the hype around genAI currently, most companies are still in the initial stages of implementing AI strategies... Most of the TAM is still on the sidelines believing that Microsoft is going to be their savior and deliver generative AI in all the places that count. And there's still a ton of white space. Most of the space is blank, to be filled by all of us." [3]
On the evolution of AI: "We started Writer in 2020. We called the company Writer because it was very clear even in those early days that AI was going to be better than people at reading and writing and certainly faster." [3]
On the hype versus the reality of generative AI: “The capabilities of large language models are transformative, but there's still much work to be done to harness their potential fully. Companies need to separate the signal from the noise and focus on real-world applications that deliver value.” [2]
On the challenge of AI implementation: “Most companies struggle with the last mile of implementation. LLMs alone aren't the solution; you need to incorporate business context, data, and workflows.” [2]
On the necessity of a full-stack approach: "It's really hard to control an end user experience in generative AI if you don't have control of the model. And given that we had chosen the enterprise lane, uptime matters, inference matters, cost of scale matters, and accuracy really matters." [4]
On the future of AI models: "I think we've realised nobody wants to build their own LLM - enterprises don't want to build their own LLMs. So I think there's a whole host of companies built on the premise that enterprises will be building their own LLMs at scale.” [5]
On smaller vs. larger language models: "I am so unequivocal about this now having been doing this for uh 3 years smaller is just better it is more efficient it's more manageable they're easier to train and fine-tune and they're they're more accurate." [6]
On the path to super intelligence: "These are models that are able to update their training data in real time so they can learn from every wrong interaction, which is going to be very critical in agentic AI." [7]

On Entrepreneurship and Building a Company

On her entrepreneurial drive: "I was born into a family of entrepreneurs and hustlers. One of my earliest memories of being in Canada was watching my immigrant dad and uncle, whose family we lived with, buy used cars, fix them, and sell them. I worked in various family businesses and knew I was going to start a company one day." [1]
On taking the leap: "I started as an entrepreneur after several years in banking and private equity, which was a huge leap of faith. I was happy there and learning a lot, but I knew that the longer I did it, the longer my salary and bonuses would become golden handcuffs and I wouldn't easily get out." [1]
On her focused entrepreneurial style: "I jokingly say that I'm a non-serial entrepreneur — I choose one space and stick to it for an unnaturally long time." [1]
On validating a startup idea: "Rarely is the first idea the right idea." [8]
On market research: "I literally read that Eric Ries book... it really was like I did feel like it was a very intentional process but you know just what really came natural talk to people who were using competing solutions to do what we were trying to do." [9]
On building a board: "We wanted to make sure that the board really represented where we wanted to be, what kind of company we wanted to be over the next few years, and really worked backwards from that." [3]
On hiring: “We keep hiring to a really high bar, but also once they come into the business, how quickly can we really operationalize them?” [3]
On the importance of slowing down to speed up: Habib highlighted the need to slow down in order to speed up, making sure they properly integrate everyone they just hired before going out and hiring more. [3]
On the importance of focus: "We're really specific about what we do and what we don't do. We don't work with agencies. We don't work with smbs." [9]
On the constant state of reselling in a noisy market: "In generative AI you actually are in a constant state of reselling. because it's such a noisy Market your buyer your Champions. there's so many shiny things come in their way." [9]

On Leadership and Vision

On communicating a vision: Successful entrepreneurs must translate their personal visions into something tangible enough to attract employees, investors, and eventually, customers. [8]
On storytelling: "I don't see myself as a storyteller, I see myself as decent at picking up signal from noise and explaining that to people." [8]
On the role of a leader in the age of AI: “Executives need to articulate a vision for AI that brings people together and helps them see the possibilities.” [2]
On creating internal AI champions: "You don't want it to be something people are doing off the sides of their desk you want it to be somebody's full-time job like making and getting business impact out of generative AI." [6]
On being contrarian: “A lot of what we've been doing has felt contrarian. We built our own models even as folks said, 'Hey, these frontier models are getting more powerful and cheaper, why don't you just build on them?' and that has really proven to be what the enterprise needs.” [10]
On embracing discomfort: “I do think over time I've gotten comfortable being uncomfortable, being scared.” [10]
On the importance of a learning organization: "Do you really become a learning organization. and so we we've now Incorporated that into our operating principles of when we act with urgency." [9]
On the partnership with customers: "There's a lot to learn for all of us and, luckily a real excitement around making that happen... it's a very close partnership with the customer. So, what we learn, they learn what they learn, we learn." [11]
On trust and shared responsibility: “Our customers are taking significant risks in adopting generative AI, so it's our job to guide them through the process.” [2]
On leading with value, not just technology: Habib emphasized that Writer's success and rapid growth are attributed to the fact that they still lead with solutions, business impact, and value — even though AI opens the door for them. [3]

On Equity, Ethics, and the Future of Work

On the dual potential of AI for equity: “I think what's interesting now is that AI has both the potential and the risk to be ten, maybe a hundred times more equity-creating or equity-exacerbating, depending on how we shape it.” [10]
On the impact of language on opportunity: “The language you were born speaking shouldn't impact the kind of life you end up leading.” [10]
On the risk of a dystopian future: “We could end up with a really dystopian future where most jobs are done by AI employees and folks who already would have been top of the food chain, you know, that much more productive as a result of having all that leverage.” [10]
On the responsibility to upskill the workforce: "It's our responsibility to really bring people along from a training and skills perspective." [12]
On rooting out bias in AI: Her goal is “to evaluate the entirety of corporate communication to tackle gender bias — and changing language is just the first step.” [1]
On the democratization of AI skills: "There's a real democratization of who can be an AI engineer today it's such a wide spectrum of technical capabilities that we can now invite to use these primitives um to do really powerful stuff." [12]
On the enduring value of human writers: Despite the rise of AI, both Phylise and May emphasize the enduring value of skilled human writers who can infuse creativity, personal stories, and authentic human interaction into their writing. [13]
On the future of jobs: "We talk about you know 50% of jobs are going away you know I don't know that I believe that at all." [12]
On the importance of diversity in AI teams: "We want them to really feel like the writer team and our generative AI pods are are really reflective of them." [12]
On the human element in the age of AI: "Our stories are what make us human. Our stories shape how we see the world, how we see ourselves, and how we impact others. In the age of AI, this simple truth will help light our way as we strive to transform the world around us for the better." [10]

On Strategy and Go-to-Market

On focusing on specific use cases: "Habib pointed out the importance of focusing on specific use cases and industries when implementing AI." [3]
On creating a "cheat sheet" for customers: “We break [use cases] down by vertical. It's kind of a cheat sheet, like where the gold is buried, based on our learnings over the past years of doing this for the enterprise.” [3]
On avoiding being too prescriptive: "There's a danger in being too prescriptive in the use cases because there are so many opportunities to create new workflows that would have been unthinkable if done manually." [3]
On the importance of understanding the customer's business: “The magic isn't when they learn how to use our building blocks, although that is very magical. It's when we can together diagram out a workflow and then build an app that actually can mimic and collapse that workflow.” [5]
On speaking the customer's language: "We challenge ourselves not to say GenAI in pitches. That's when you know you're having a real conversation with somebody.” [5]
On the challenge of enterprise adoption: "Change management is a big deal uh when you are really trying to get your people to be more efficient internally using generative AI." [6]
On the importance of ROI: “You know, some of these numbers are so crazy in terms of ROI that we pare it down a lot. Because no CIO is going to believe 50x ROI. They have been burned so many times." [5]
On the "over-chat-ification" of AI: Her take on the “over-chat-ification” of AI products, the reliance on chat interfaces as opposed to other ways to access AI capabilities. [14]
On the importance of an investor who understands the space: "It's really important to have an investor who understands the space inside and out." [8]
On the future of AI interfaces: Her company is pioneering approaches like “headless AI” to help employees across an enterprise use AI to be more creative and productive. [14]

Learn more:

Lessons from May Habib

On the Transformative Power and Reality of AI

On Entrepreneurship and Building a Company

On Leadership and Vision

On Equity, Ethics, and the Future of Work

On Strategy and Go-to-Market

Written by Antoine Buteau

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