Grammarly's core value was alleviating the deep-seated anxiety of writing. This emotional connection, which gave users confidence, was key to its initial success and proved more powerful than a purely functional benefit of correcting grammar.
Grammarly's new agent is designed around three attributes: it works everywhere, it proactively offers help, and it's connected to user data across platforms. This trifecta creates a powerful, integrated user experience that feels seamless and intelligent.
The most retentive products eliminate the "drudgery" of work by making complex tasks feel simple and intuitive. Users are hooked by the feeling of being in their natural flow, a more powerful motivator for retention than purely functional metrics like time saved.
A key to M&A success is creating a founder-friendly environment. Avoid killing entrepreneurial spirit by forcing founders into a rigid matrix organization. Instead, maintain the structures that made them successful and accelerate them by providing resources from the parent company.
In today's fast-paced tech landscape, especially in AI, there is no room for leaders who only manage people. Every manager, up to the CPO, must be a "builder" capable of diving into the details—whether adjusting copy or pushing pixels—to effectively guide their teams.
To scale to a multi-product company, Grammarly treats each acquired product as its own "startup" with its own P&L. They are tightly aligned on vision but loosely coupled in execution, preserving founder autonomy while leveraging shared platform services like billing and identity.
Even if your strategy is a ubiquitous AI layer, building your own applications (like an email client) is essential. These dedicated "surfaces" allow you to fully express your vision for an AI-native experience, which is constrained when only building on top of others' products.
User workflows rarely exist in a single application; they span tools like Slack, calendars, and documents. A truly helpful AI must operate across these tools, creating a unified "desired path" that reflects how people actually work, rather than being confined by app boundaries.
To assess a product manager's AI skills, integrate AI into your standard hiring process rather than just asking theoretical questions. Expect candidates to use AI tools in take-home case studies and analytical interviews to test for practical application and raise the quality bar.