Customer Operations & Writing Specialist

About Clerky

At Clerky, Inc., 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 technology companies for everything from forming to hiring and fundraising.

If you’ve ever watched a great company win through word-of-mouth, you’ll understand our approach: we earn trust by delivering consistently excellent support—especially when customers are under real time pressure.

About The Role

As a Customer Operations & Writing Specialist, you’ll be the voice of Clerky for thousands of founders, investors, and attorneys. You’ll help customers complete critical legal paperwork using our platform—and you’ll do it through clear, precise, empathetic writing.

This is not a “quick reply” role. Customer questions are nuanced, often specialized, and sometimes don’t have a simple answer. Your job is to think critically, communicate exceptionally well, and guide customers toward what they can do next—with confidence and clarity.

What You’ll Do

You’ll be responsible for high-quality customer support and continuous improvement across documentation and product feedback. Day to day, that means:

• Write thoughtful, empathetic email responses to customer inquiries using our help desk system (Help Scout).
• Create, update, and maintain Help Center articles that reduce repeated questions and improve customer self-service.
• Identify new documentation opportunities by analyzing patterns in customer emails and requests.
• Partner with Engineering to debug software issues customers encounter—turning real-world support signals into actionable fixes.
• Use our product to improve how customers complete legal paperwork, including developing and managing new workflows or ways customers can get their work done.
• Assist the Product team by testing new features and bug fixes, then clearly conveying what you learn from customer interactions.
• Spot trends in customer issues so the right teammates are alerted early and improvements happen faster.

You’ll also help shape how we think about support quality—because at Clerky, “good enough” isn’t the goal. We’re building a craft, not just a queue.

Why This Role Is Different

• Helping customers is unusually challenging. Questions can be technical, time-sensitive, and legally adjacent—meaning your writing must be careful, accurate, and useful.
• Iteration is part of the work. You’ll often refine responses with feedback, so you’ll need to think logically and improve continuously.
• Learning is constant. You’ll build real knowledge about startups and startup-related legal processes simply by doing the job.
• Sometimes there are no definitive answers. You’ll help customers figure out next steps, understand what’s knowable, and recognize when the right answer can’t be determined from the information provided.

If you prefer environments where you can “master everything quickly” and then run on autopilot, this likely won’t be a fit. If you enjoy sustained focus, careful writing, and ongoing improvement, you’ll probably love it here.

What We’re Looking For

We care about your instincts and your communication style as much as your execution. Specifically:

• Genuine love for helping people — and doing it in a way that respects their situation.
• High emotional intelligence — you can empathize without guessing, and you can stay calm when customers are stressed.
• Logical / analytical thinking — you can break down complex questions and reason through uncertainty.
• Exceptional written English communication skills — including the ability to write precisely and succinctly.
• Extremely detail-oriented — your work should feel accurate, polished, and deliberate.
• Comfort working remotely and independently — you can manage your time and stay productive without constant oversight.
• Technologically savvy — you should be confident learning new software tools without needing extensive training.
• Comfort giving and receiving feedback frequently (often multiple times per day).
• Natural internal motivation to strive for excellence in everything you do.

No legal experience is required. In fact, we don’t expect you to come in with a legal background. What matters is how you think and how you write.

How We Work

• Remote-first (always). Clerky has been remote-first for many years—long before COVID.
• Small team, big impact. Everyone’s contributions matter, and your work directly improves customer outcomes.
• Autonomous and efficient. We move quickly, with trust and respect for one another.
• Open collaboration. We work transparently and support you as you ramp up and grow in the role.
• Flexible schedules. Hours are adjustable as long as we maintain adequate team coverage.
• Growth budget. We provide funding for books, courses, tools, or other learning resources.

Benefits

You’ll receive top-of-market compensation and benefits, along with the opportunity to learn a lot while helping customers during an exciting time in their lives.

• Work from anywhere (100% remote)
• Reasonable hours and a sustainable pace
• Supportive team environment with strong collaboration and feedback
• Learning and development budget for ongoing skill building
• Compensation aligned with market

Location, Schedule, and Hiring Notes