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2025-11-04-checkr-head-internal-communications-cover-letter

Monday, November 4th, 2025

Dear Checkr Hiring Team,

I'm applying for the Head of Internal Communications role because Checkr's mission to power safe and fair decisions through data requires exceptional communication to succeed at scale.

I've spent my career at the intersection of complex technology and clear storytelling. I know how to distill complex concepts into compelling narratives. I've advised executives at the highest levels. And I've developed a framework for exactly what this role demands: creating alignment across growing teams through what I call "truth management."

Why I'm a Fit​

I Understand What Breaks When Communications Fail​

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 scaled, information was scattered. Leadership assumptions weren't 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: organizations 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 is helping teammates understand the vision, goals, and executive updates in ways that actually land and inspire action.

That's exactly what this role exists to solve. And I have both the framework and track record to deliver it.

I'm a Strategic Leader Who Can Toggle to Doer​

I'm comfortable being a trusted advisor to C-suite executives on high-stakes communications. I currently advise the Catholic Church in Rome on digital transformation. I've worked with the White House faith office. I consulted for a billionaire in edtech. I know how to provide strategic counsel, navigate sensitive matters with discretion, and operate in high-visibility environments.

But I'm also a doer. I don't just strategize communications. I execute them. I know how to move from concept to delivery quickly and with exceptional quality.

I Bring Technical Fluency + Exceptional Storytelling​

I started my career as a Software Engineer at Google Cloud from 2015 to 2019, leading a small team. I understand the technology industry deeply. I speak the language of product, engineering, and data teams. This technical fluency means I can help Checkr teammates understand complex product positioning and technical updates in ways that resonate.

But my real superpower is translating technical sophistication into compelling narratives:

  • Built a youth nonprofit that trained thousands globally in complex civic concepts. Named Forbes 30 Under 30 for this work.
  • Made crypto concepts like Sybil defense and regenerative web3 compelling to mainstream audiences, growing Gitcoin Passport from 200,000 to 1M users through strategic communications.
  • Organized Edge City Denver 2024—a seven-day event with 3,000+ attendees and 4.6/5 average satisfaction. Designed programming, recruited speakers, and created messaging that engaged diverse technical audiences.

I know how to work cross-functionally with HR, Marketing, Product, R&D, and Leadership to execute communication initiatives that engage, connect, and inspire.

I'm Fearless About Embracing Technology​

I'm a sophisticated user of AI and other technology solutions. I recently graduated top of my class from Gauntlet AI, an AI-first coding bootcamp. I use AI daily to scale my impact and enhance communication quality. I understand how to leverage technology to produce content faster, maintain editorial calendars more efficiently, and reach employees across multiple channels effectively.

I'm excited about using technology to help Checkr's internal communications stay ahead of the curve as you prepare for your next phase of growth.

I've Developed a Framework for Internal Communications at Scale​

I call it "truth management": the discipline of helping organizations document and evolve the shared operational knowledge that enables aligned action. For Checkr specifically, this means:

  • Strategic alignment: Ensuring messaging aligns with company vision, mission, and product positioning
  • Cross-functional collaboration: Building strong culture of collaboration across teams
  • Multi-channel execution: Producing employee communications across variety of channels
  • Narrative consistency: Developing strategic narrative and thought leadership strategy that's consistent across all touchpoints

My career has shown me why this matters and made me passionate about implementing it. It's the same approach Checkr needs to maintain alignment and build strong culture as you scale.

I Thrive in Fast-Paced, High-Growth Environments​

I'm organized and creative. I can adapt and change directions in an instant. I've worked in unstructured, fast-paced environments where tight deadlines are the norm. I've managed multiple priorities simultaneously while maintaining exceptional quality.

I've consistently chosen to work with high-growth companies at inflection points because that's where internal communications matters most.

My Commitment​

Checkr is at an exciting inflection point. As you prepare for your next phase of growth, the quality of internal communications directly impacts whether the team feels engaged, connected, and inspired by the mission.

I want to be the person who develops and executes the strategic internal communications plan that makes this happen. I want to help craft the messaging for leadership meetings, produce compelling content across channels, and partner with C-suite on thought leadership and brand evangelism.

Most importantly, I want to bring my truth management framework to bear on helping Checkr teammates understand your vision for powering safe and fair decisions as you continue building trusted workplaces and communities.

I'd love to discuss how my experience advising executives at the highest levels, my technical fluency combined with exceptional storytelling, and my framework for creating alignment at scale can help Checkr achieve its mission.

Thank you for your consideration.

Gary Sheng