Customer Operations & Writing Specialist

Customer Operations & Writing Specialist (Clerky)

At Clerky, we help startups and their attorneys complete essential legal paperwork—faster, clearer, and with less stress. If you’re the kind of person who can take a messy question, think it through carefully, and respond with precision and empathy, this role is built for you. As our Customer Operations & Writing Specialist, you’ll be the trusted voice of the company for founders, investors, and legal professionals who often need answers on tight timelines. And because our growth is driven by word-of-mouth, “great service” isn’t a slogan—it’s the standard.

About Clerky

Clerky builds software that makes legal paperwork easier for high-growth technology startups. We’re profitable and growing sustainably. We’re a leading platform for forming startups and are also used by many top-tier companies for hiring and fundraising.

We’re proud of our customer satisfaction and the culture behind it: we’re rabidly customer-centric, and we take the craft of written communication seriously.

What Makes This Role Different

This isn’t a “generic support” job. Helping customers at Clerky can be genuinely challenging because the questions we receive are nuanced, specialized, and often require iterative thinking. In many cases, there isn’t a single definitive answer we can hand back—your job is to provide the right information, the right framing, and the right next steps so customers can move forward with confidence.

• Hard problems, not easy scripts: You’ll need to think critically, write thoughtfully, and refine your responses.
• Continuous learning: You’ll pick up real knowledge about startups and startup law as part of the work.
• No “always right” answers: Sometimes the best outcome is helping customers understand what’s knowable, what isn’t, and how to decide.
• High focus required: The quality bar for writing is intense—this role rewards sustained attention and craftsmanship.

What You’ll Do

You’ll support customers primarily through written communication and help-center documentation—while partnering closely with engineering and product to improve the experience.

• Write empathetic, precise email responses to customer questions using our help desk tool (Help Scout).
  • Communicate clearly and succinctly, even when the question is complex.
  • Adjust tone to match founders, investors, and attorneys—always with care and respect.
• Write and maintain help center articles
  • Keep existing documentation accurate and up to date.
  • Identify new article opportunities based on recurring customer inquiries.
• Collaborate with engineering to debug customer issues
  • Investigate software problems customers encounter.
  • Help translate customer experience into actionable technical insights.
• Use our product to improve how customers complete legal paperwork
  • Develop and manage new ways for customers to complete legal workflows.
  • Support improvements by identifying friction points and opportunities.
• Support product quality by testing features and fixes
  • Test new functionality and bug fixes.
  • Share customer feedback in a way that helps the team ship better outcomes.
• Spot trends and escalate what matters
  • Identify patterns in customer issues so the right teammates are alerted.
  • Help prevent repeated confusion and improve the overall customer experience.

How We Work

• Remote-first (long before COVID): Clerky has been remote-first for many years, so distributed work is built into how we operate.
• Small team, big impact: Everyone’s contributions matter. You’ll work efficiently and autonomously, with mutual respect.
• Open, collaborative culture: We support one another and work openly to help you succeed in the role.
• Flexible schedules: We trust you to manage your time effectively as long as there’s adequate team coverage.
• Growth budget: We provide a budget for books, courses, tools, or other educational resources to help you level up.

We work hard, but we also trust people to do their best work—and to communicate clearly about what will make them most productive.

What We’re Looking For

You don’t need legal experience to succeed here. What matters is how you think, how you write, and how you treat people.

• Genuine love for helping people
• High emotional intelligence — you can be empathetic without losing clarity
• Logical, analytical thinking — you can reason through ambiguity
• Exceptional written English
  • Ability to write precisely and succinctly
  • Strong editing instincts and attention to wording
• Extremely detail-oriented — you notice what others miss
• Comfort working remotely and independently
• Technologically savvy
  • Confident using new software without extensive training
• Comfort giving and receiving feedback frequently (often several times per day)
• Internal drive to pursue excellence in your work, every day

Benefits & Compensation

Clerky offers top-of-market compensation and benefits, reasonable hours, and reasonable customers. You’ll also have the opportunity to learn a lot while helping customers through an exciting stage of life.

• Remote-first flexibility
• Books/courses/tools budget for growth
• Top-of-market compensation and benefits
• Supportive team and strong culture of feedback

Remote Work Details

This is a 100% remote position. You can work from home (or from anywhere else).

AI Tools in the Hiring Process

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 ultimately made by humans.

Ready to Join Us?

If you thrive in a role that demands careful thinking, excellent writing, and continuous improvement—without relying on easy answers—this could be a great match. Apply and show us how you approach complex questions with clarity and empathy.