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2025-10-28-notion-head-internal-communications-cover-letter

Wednesday, October 29th, 2025

Dear Notion Hiring Team,

My name is Gary Sheng. I'm a software engineer, writer, and movement builder who has spent years helping technically sophisticated teams stay aligned as they scale.

I'm applying for the Head of Internal Communications role because I believe Notion is building one of the most important tools for human creativity and collaboration. And I believe I can provide what Notion needs to responsibly scale: keeping everyone aligned on what matters most through what I call "truth management."

Why I'm the Right Fit​

I Understand What Breaks When Companies Scale​

I recently completed a consulting contract with an early-stage tech-focused school system. The organization had talented people and an exciting vision from the founder. But as it had been scaling, it was falling apart. Information was scattered. Leadership assumptions weren't usually documented or shared. Teams operated on different operational truths. Critical context lived primarily in people's heads, with sometimes intentional siloing to protect fiefdoms.

This experience crystallized something I've believed for years: companies don't just fail from lack of talent or strategy. They fail from misaligned assumptions about what matters and how to operate. As companies scale, the challenge isn't just broadcasting information. It's the deeply human challenge of helping people with different worldviews, backgrounds, and contexts feel seen, connected, and aligned around what matters most (aka the “truth” of the organization).

That's exactly what this role exists to solve. And it's what I'm most passionate about.

I'm Passionate About the Problem of Internal Alignment​

I care deeply about people. I understand that organizations are made up of individuals with different perspectives, experiences, and ways of seeing the world. Getting alignment isn't about forcing everyone to think the same way. It's about creating the conditions where diverse perspectives can coexist while everyone still moves in the same direction.

As companies scale, this becomes exponentially harder and exponentially more important. The challenge is:

  • Proactively identifying what context people will need before they know they need it
  • Designing information flows where the right messages reach the right people with less noise
  • Helping founder vision cascade coherently while making space for how different teams interpret and apply it
  • Tracking whether communications actually land in ways that help people feel connected and informed

My career has given me a lot of time to think deeply about organizational alignment. I call it "truth management": the discipline of helping organizations document and evolve the shared operational knowledge that enables aligned action.

I Create Alignment at Scale Through Story and Structure​

I've spent years getting diverse groups of people aligned around complex, transformative missions:

  • Edge City Denver: Organized a seven-day event that drew 3,000+ founders and builders across crypto, AI, and biotech. Average satisfaction: 4.6/5. I designed the programming, recruited speakers, managed stakeholder alignment, and built buzz through consistent, compelling communication. This required orchestrating complex narratives across dozens of partners.
  • Democracy reform: Built a youth nonprofit that trained thousands globally. Named Forbes 30 Under 30 for this work. The Rock shouted us out on Instagram. Success required making complex civic concepts feel accessible and inspiring to youth worldwide.
  • Web3 ecosystems: Secured grants from Ethereum Foundation, Coinbase, and Celo by distilling technical visions into narratives that got buy-in from senior executives and community members simultaneously.
  • High-stakes advising: I advise the Catholic Church in Rome on digital transformation. I'm comfortable operating at the highest levels with discretion, empathy, and care.

For all these projects, Notion was used extensively to manage information and create alignment both internally and externally.

I'm a Builder Who Understands Notion's Audience​

I started my career as a Software Engineer at Google Cloud from 2015 to 2019. I recently graduated top of my class from Gauntlet AI's coding bootcamp. I understand how technical people think. I was an early power user of Notion and still use it religiously. I get the product's creative power and the builder mindset of your customers because I am one. Years ago, I even presented to Simon and a few colleagues how I personally use Notion!

My Commitment​

As you scale from thousands to millions of users, keeping your internal team aligned on that mission becomes exponentially harder and exponentially more important.

I want to be the person who ensures everyone at Notion feels connected to the mission through the stories we tell about their work. I want to design the information architecture that makes the right messages reach the right people with less noise. I want to work with your founders to distill their vision into moments that inspire your global team.

Most importantly, I want to take on one of the most interesting scaling challenges in tech: keeping a creative, distributed team aligned as Notion reaches its full potential.

Thank you for your consideration.

Best regards,

Gary Sheng