Customer Operations & Writing Specialist

About Clerky

At Clerky, Inc., we build software that helps startups and their attorneys handle legal paperwork faster, more accurately, and with far less friction. We’re profitable, growing sustainably, and trusted by high-growth technology companies to form, hire, and fund. If you’ve ever wished legal administration felt less like a maze and more like a guided workflow—this is that mission.

As a Customer Operations & Writing Specialist, you’ll be the human voice behind that experience. Thousands of founders, investors, and attorneys will rely on you when they need clarity on time-sensitive legal paperwork questions—often under real pressure. Because our growth is driven by word-of-mouth, we don’t just “respond.” We deliver service that earns trust.

About The Role

You’ll write the responses our customers see and feel. Your work will combine careful judgment, crisp writing, and genuine empathy. Questions won’t always have clean, definitive answers—so you’ll help customers understand what’s knowable, what isn’t, and what they should do next. In many cases, your best contribution will be equipping customers with the information they need to figure it out with confidence.

This role is intentionally craft-heavy. You’ll learn a lot about startups and startup law along the way, but the real differentiator is how you think and how you write: precisely, succinctly, and with high emotional intelligence.

What You’ll Do

• Write thoughtful, empathetic email replies to customer questions using our help desk system (Help Scout), ensuring responses are clear, accurate, and actionable.
• Maintain and improve our help center by writing help center articles and identifying topics for new articles based on recurring customer inquiries.
• Partner with Engineering to debug and troubleshoot software issues customers encounter—turning customer reports into useful, reproducible insights.
• Use our product to improve customer outcomes by developing and managing new ways for customers to complete legal paperwork.
• Support Product quality by testing new features and bug fixes, then conveying customer feedback in a way Engineering can act on.
• Spot patterns and escalate trends so other team members are aware of recurring issues and opportunities to improve.

What Makes This Customer Operations Role Different

• It’s unusually challenging—in the best way. Customer questions are nuanced and specialized. You’ll often need iterative feedback to get the writing and guidance right.
• You’ll keep learning. You’ll build real familiarity with startups and startup law, not through memorization, but through repeated exposure to real customer scenarios.
• There may be no “perfect” answer. We can’t always provide definitive legal outcomes. Your role is to help customers navigate uncertainty responsibly and effectively.
• Craft requires focus. The quality bar for writing is high. This isn’t a role where you can coast—accuracy, attention, and consistency matter.

What We’re Looking For

• Genuine love for helping people—you care about the outcome, not just the response.
• High emotional intelligence—you can communicate clearly and kindly, especially when customers are stressed or confused.
• Logical and analytical thinking—you can reason through complex situations and structure a helpful answer.
• Exceptional written English—you write precisely and succinctly, and you naturally edit for clarity.
• Extreme attention to detail—you notice what others miss, and you take correctness seriously.
• Comfort working remotely and independently—you can manage your time and deliver reliably without constant supervision.
• Technologically savvy—you can ramp quickly on new tools and software without needing extensive training.
• Comfort giving and receiving feedback often—sometimes multiple times per day.
• Internal drive to continuously improve—you naturally strive for excellence in your work.

No legal experience required. You don’t need a legal background to do well here. What matters most is your writing, judgment, and ability to learn quickly.

How We Work

• Remote-first, long before COVID. Clerky has been remote-first for years, and we’re comfortable collaborating across time and distance.
• Small team, big impact. Everyone’s contribution matters. We work efficiently and autonomously, with genuine respect for one another.
• Open and collaborative communication. We support you in succeeding in the role, and you’ll work closely with teammates to ensure customers get the best possible experience.
• Flexible schedules with coverage. We trust you to know what helps you be most productive—within reasonable coverage needs.
• Growth is built in. There’s a budget for books, courses, tools, or any other educational resources you need to level up.

Benefits & Compensation

• Top-of-market compensation and benefits
• Reasonable hours and a sustainable pace
• Reasonable customers—we prioritize support quality and clarity
• High-impact work during an exciting time in customers’ lives
• Opportunity to learn a lot by solving real problems for real people

Location & Work Arrangement

• 100% remote — work from home (or anywhere else)

AI & Hiring Transparency

We may use artificial intelligence (AI) tools to support parts of the hiring process, such as reviewing applications, analyzing resumes, or assessing responses. These tools assist our recruitment team but 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?

If you’re the kind of person who takes writing seriously, enjoys iterative improvement, and genuinely wants to help customers succeed—even when the answer isn’t obvious—this role is for you.

Note: Clerky is seeking a Customer Operations & Writing Specialist. Apply if you match the criteria above and want to do meaningful, craft-focused work in a remote-first environment.

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