Customer Operations & Writing Specialist

Customer Operations & Writing Specialist — Help Founders Move Faster

At Clerky, we build software that makes legal paperwork easier for startups and the attorneys who support them. We’re profitable, growing sustainably, and trusted by high-growth teams when time matters. As a Customer Operations & Writing Specialist, you’ll be the voice of Clerky—helping thousands of founders, investors, and attorneys get the right legal paperwork completed with confidence.

Because our growth is driven by word-of-mouth, we take customer experience seriously. This role is for someone who can write with clarity and empathy, think critically through nuanced questions, and continuously raise the bar on quality.

About The Role

Customer Operations at Clerky isn’t a “one-size-fits-all” support job. Your work will involve specialized, detail-heavy questions and scenarios where we often can’t provide a single definitive answer. Instead, you’ll help customers understand what they can do, what they should consider, and how to move forward intelligently.

You’ll also contribute to our knowledge base, partner with engineering to troubleshoot issues, and help shape how customers complete legal paperwork through product feedback and testing.

What You’ll Do

• Write thoughtful, empathetic responses to customer emails using our help desk system (Help Scout).
• Craft and maintain Help Center articles, ensuring our documentation is clear, accurate, and genuinely helpful.
• Identify gaps and new content opportunities by analyzing customer inquiries and spotting patterns worth documenting.
• Collaborate with engineering to debug software issues customers encounter—translating customer impact into actionable technical context.
• Use Clerky’s tools to improve workflows, helping develop and manage new ways for customers to complete legal paperwork.
• Support product quality by testing new features and bug fixes, then communicating what you learn back to the team.
• Surface trends early so other team members can address recurring issues and prevent customer friction.
• Iterate relentlessly—your best work will come from feedback loops, careful revision, and continuous improvement.

What Makes This Role Different

• It’s harder (in the best way). Customer questions can be nuanced and specialized, requiring careful reasoning and precise writing.
• There’s often no “perfect” answer. You’ll equip customers with the information and framing they need to make the right decision for their situation—or recognize when the right answer can’t be determined.
• Quality requires focus. The writing craft here takes intense attention to detail. If you want a role you can “set and forget,” this won’t feel right.
• You’ll learn constantly. You’ll pick up deep context about startups and startup law through real customer interactions.

What We’re Looking For

• Genuine love for helping people—not just solving tickets, but improving outcomes.
• High emotional intelligence to communicate clearly and empathetically under time pressure.
• Strong logical/analytical thinking to work through complex questions and edge cases.
• Exceptional written English—able to write precisely and succinctly, without losing nuance.
• Extreme attention to detail, especially when accuracy and clarity matter.
• Comfort working remotely and independently in a small team where ownership matters.
• Technological confidence—you should be comfortable learning new software quickly without extensive training.
• Comfort with frequent feedback (often several times a day) and a willingness to refine your work.
• Internal drive for excellence—you naturally strive to do things better, not just “done.”
• No legal experience required—and no legal background is preferred or expected.

How We Work

• Remote-first, always. Clerky has been remote-first for years, long before COVID.
• Small team, big impact. Your contributions matter, and you’ll work efficiently with autonomy.
• Open collaboration. We work transparently and support each other so you can succeed.
• Flexible schedules. We trust you to manage your time—flexibility is available as long as there’s proper team coverage.
• We invest in your growth. You’ll have a budget for books, courses, tools, and other learning resources.
• Top-of-market compensation and benefits. Plus, you’ll learn a lot while helping customers during an exciting time in their lives.

Benefits

• 100% remote work (work from home or anywhere else)
• Top-of-market compensation and benefits
• Reasonable hours with a sustainable pace
• Reasonable customers—we build for clarity, and we support people with care
• Continuous learning budget for professional development
• Supportive, high-craft team that takes quality seriously

Important Notes on Hiring & AI

We may use AI tools to support parts of the hiring process (for example, reviewing applications, analyzing resumes, or assessing responses). These tools assist our recruitment team and do not replace human judgment. Final hiring decisions are made by humans. If you’d like more information about how your data is processed, please contact us.

Ready to Join Clerky?

If you’re energized by precise writing, thoughtful customer support, and constant improvement—and you want to help founders and attorneys navigate critical paperwork with confidence—this role is built for you.

Apply now and tell us what kind of feedback-driven work you thrive in, and how you approach writing when the “right answer” isn’t always obvious.

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