WORKED SAMPLE ·Customer Operations & Writing Specialist·Remote
ⓘ Independent job-application page, not affiliated with or operated by Clerky, Inc. The sample replies below are illustrative writing, not legal or tax advice, and not real Clerky correspondence.

The job is writing that a founder can act on under pressure, when there's often no clean answer.

The posting is unusually honest: it's hard here, the questions are nuanced, and Clerky often can't hand over a definitive answer. So the fairest thing I can send is not a pitch about myself. It's the actual work: four customer replies written the way Clerky writes, a help-center article I drafted, and a read of the support surface. Judge the writing, not the adjectives.

PreciseEmpatheticSuccinctKnows the guardrails
The one-paragraph version

Clerky's customers are founders, investors and attorneys doing legal paperwork that has real consequences, often against a deadline. A good reply does three things at once: it lowers the customer's stress, it is precise about what is and isn't true, and it stays inside the line Clerky can't cross, which is that Clerky is software, not a law or tax firm. The craft is saying "here's what we can tell you, here's what only your attorney can" without making the customer feel abandoned. This page shows me doing exactly that, four times, plus an article and a plan.

What's on this page
  • A read of what makes Clerky support genuinely hard
  • How Clerky's support differs from Atlas, Carta, LegalZoom
  • Four full customer replies I wrote
  • A help-center article, drafted end to end
  • Each JD responsibility mapped to a plan
  • The principles I write support by
01

Clerky, in context

Formation
Delaware C-corps, the startup default
+ Hiring
equity grants, option pools, 83(b)
+ Fundraising
SAFEs, convertible notes, priced rounds
Profitable
word-of-mouth, service-led, remote-first

Clerky makes the legal paperwork of a startup safe to do without a lawyer in the room: incorporating, issuing founder stock, granting options, and raising money on SAFEs or notes. Its customers reach for it at the highest-stakes moments of a company's early life, and its growth is word-of-mouth, which means every support reply is a retention and referral event, not a cost center. The company is small, profitable and remote-first, so a support person is close to the whole business: the docs, the product, the engineers, and the customer's actual outcome.

02

Why this support is genuinely hard

The posting warns three times that this job is harder than it looks. I read that as a filter, and I agree with it. Here is the specific difficulty, and why writing is the actual skill being hired.

The stakes are real and timed

An 83(b) election has a hard 30-day IRS window with no extensions. A founder issuing stock at the wrong price or date creates a problem a reply can't undo. You cannot be breezy, and you cannot be wrong.

There is often no right answer

SAFE or priced round? Vest over three years or four? These are judgment calls Clerky can't make for the customer. The job is to equip them to decide, or to say plainly that only their attorney can.

The guardrail is the hardest part

Clerky is software, not a law or tax firm. Every reply has to be genuinely helpful while staying on the right side of that line. Warm and precise and bounded, all at once, several times a day.

So the skill is

Writing a precise, calm, correct answer that respects a hard boundary and still leaves the customer feeling helped. That is exactly the thing the samples below try to demonstrate, on the exact kinds of questions Clerky actually gets.

03

How Clerky support differs from the neighbors

Founders often arrive having tried a neighbor first. Knowing why Clerky's answer is shaped differently is part of writing a good reply.

ToolWhat it isWhy Clerky's support reads differently
Clerky this roleSelf-serve legal paperwork for startups, service-ledAnswers are precise and bounded on purpose: it equips founders to do the paperwork correctly and points to an attorney for judgment, rather than deciding for them.
Stripe AtlasIncorporation bundled with banking and paymentsOptimized for a fast, standardized formation path; less depth on the messy post-incorporation and fundraising edge cases Clerky is built around.
CartaCap-table and equity management platformStrong on ongoing equity administration; Clerky sits earlier, at the moment the documents that create that equity are generated and signed.
LegalZoom / Rocket LawyerGeneral-purpose legal documents and servicesBroad but not startup-native; a Clerky reply assumes the specific vocabulary of SAFEs, 83(b), option pools and Delaware C-corps.
A startup law firmActual legal advice and representationThe one thing Clerky is not. Good support names this boundary clearly and warmly, and hands off to counsel when a question crosses it.

Positioning is my read from public product pages and common founder workflows, not from any internal Clerky material.

Four customer replies, written

Each is a realistic, made-up ticket in Clerky's world. I wrote the reply, then added a short note on the choices behind it. These are illustrative and not legal or tax advice.

Ticket 01 panic · hard deadline · high stakes
Hi. I formed my company through Clerky about 5 weeks ago and a friend just told me I was supposed to file an "83(b) election" within 30 days. I don't think I did that. Did I just ruin my company?? Is there any way to fix this? I'm honestly freaking out a bit.
My reply Edward, Customer Operations

Thanks for writing in, and take a breath: this is a common worry and worth getting exactly right rather than guessing, so let's look at the actual dates together.

One important thing first: the 30-day 83(b) clock runs from the date your shares were issued to you, not from the date the company was formed. Those are often a few days apart, and sometimes more. So "5 weeks since incorporation" doesn't necessarily mean the window has closed. You can see your exact stock issuance date in Clerky under your company's Stock section, on the founder's stock purchase record. That date is the one that matters.

Here's the honest boundary: Clerky is software, not a law or tax firm, so I can't tell you whether your specific window is still open, or what the right move is if it has closed. Those depend on your situation and are decisions for a tax professional or startup attorney. What I can do is make sure you're looking at the correct date and have the filing materials ready to move quickly if you're still in time.

If you send me your Clerky company name, I'll point you to the precise spot where your issuance date and 83(b) filing instructions live, today. And if it turns out the timing is tight, I'd get a tax advisor on it in parallel rather than wait on us. You're not the first founder to hit this, and it's usually more fixable than it feels right now.

Why it's written this way: the first job is to lower panic without lying ("take a breath" earns the right to then be precise). The single most useful fact, that the clock starts at issuance not formation, is stated plainly and early. The guardrail is named honestly, then softened by giving a real next step Clerky can take. It ends with a concrete action and a true reassurance, not a hollow one.
Ticket 02 no right answer · asking us to decide
Quick one: should I raise on a SAFE or do a priced round? Which does Clerky recommend for a first raise?
My reply Edward, Customer Operations

Good question, and I want to be straight with you: Clerky won't recommend one over the other, because the right choice depends on your round size, your investors, and legal and tax factors that are specific to you. That's genuinely a call for you and your attorney, not for us. What I can do is lay out the tradeoff so that conversation is faster.

In broad strokes: SAFEs are lighter, quicker and cheaper to sign, which is why many first raises use them, they defer the valuation question to a later priced round. A priced round sets a valuation now and issues actual shares, which is more involved and usually more expensive to paper, but some investors prefer it. Neither is "safer" in the abstract; they just push complexity to different moments.

Clerky supports both. If you go the SAFE route, we generate the standard post-money SAFEs and walk you through sending them for signature; if you go priced, we support that document set too. Once you and your attorney have decided on the direction, I'm happy to point you to the exact workflow for whichever you pick.

Why it's written this way: the customer asked us to make a judgment call we can't make. The reply refuses clearly in the first line so there's no false hope, but immediately converts the "no" into value by framing the tradeoff, which is the thing Clerky can do. It stays factual and avoids anything that reads as investment or legal advice, then routes back to the product once the decision is theirs.
Ticket 03 software bug · needs an engineer · frustrated
This is the third time I've tried to send my co-founder's stock purchase agreement for signature and it just fails. I click "Send for signature," it spins, then nothing happens and the doc stays in draft. We have an investor call tomorrow and I need this done. What is going on?
My reply Edward, Customer Operations

Sorry you've hit this three times, especially the night before an investor call. Let's get it unblocked and get an engineer the details in parallel so this doesn't cost you tomorrow.

Two things would help me pin it down quickly: (1) which browser and version you're on, and whether it also fails in a private or incognito window, and (2) the moment it fails, does the co-founder's email field show as fully saved, or is any signer detail still blank? A signature send failing silently is very often a single missing signer field or a browser extension blocking the request, both of which we can work around fast.

In the meantime, one reliable path: try the send from an incognito window with extensions off. If it goes through, we've found it. If it still fails, reply with the two answers above plus the approximate time you last tried, and I'll file it to our engineering team with your account and a timestamp so they can trace the exact request rather than guess.

Either way, I'll stay on this with you tonight until your co-founder has the document to sign. You won't be walking into that call with it still stuck.

Why it's written this way: a frustrated user with a deadline needs momentum, not sympathy alone. It opens by naming both the frustration and the deadline, then does real triage: a likely-cause hypothesis (missing field / extension), a specific reproduction ask, and an immediate workaround so they aren't blocked while engineering looks. The last line is a genuine commitment, which is what turns a bug into a retained customer.
Ticket 04 nuanced edge case · non-US founder
I'm based outside the US and don't have an SSN. Can I still use Clerky to form a Delaware C-corp, and will the lack of an SSN block any of the steps?
My reply Edward, Customer Operations

Yes, founders outside the US do form Delaware C-corps through Clerky regularly, so being non-US isn't a blocker to getting started. There are a couple of spots where not having an SSN changes the path rather than stopping it, and I want to flag them honestly up front so nothing surprises you halfway through.

The main one is the EIN, the company's federal tax ID. The fastest online EIN route generally assumes a US SSN or ITIN for the responsible party; without one, the IRS process still works but runs through a different, slower channel. That's an IRS rule rather than a Clerky limitation, and it affects timing more than eligibility. The formation documents themselves, founder stock, and the core Clerky workflow don't require an SSN.

Because the exact right handling of the EIN and any tax-residency questions depends on your specific situation, that part is worth a quick check with a tax advisor familiar with non-US founders, it's the kind of thing where a professional saves you real time. I can point you to Clerky's guidance for international founders and walk you through the formation steps that aren't affected, so you can make progress today on everything that isn't waiting on the EIN.

Why it's written this way: the honest answer is "yes, with nuance," and burying the nuance would be worse than stating it. It separates what Clerky controls (the documents, the workflow) from what an external rule controls (the IRS EIN process), so the customer knows where the friction actually comes from. It flags the tax-advisor boundary without making the customer feel stranded, and still leaves them something to do right now.
04

A help-center article, drafted

One JD duty is writing and maintaining help-center articles, and spotting the topics that need one. Ticket 01 is exactly the kind of recurring, high-stakes question that deserves a standing article so founders find it before they panic. Here's the draft I'd propose.

HELP CENTER · STOCK & EQUITY
What is an 83(b) election, and why does the 30-day deadline matter?

Short version: if you received stock that vests over time, an 83(b) election is a form you file with the IRS to be taxed on the stock's value now, while it's low, instead of later as it vests. It must be filed within 30 days of when your stock was issued. That deadline is strict, and missing it can't be undone.

Why founders care about it

Most founder stock is subject to vesting, meaning the company can buy back unvested shares if you leave early. Without an 83(b) election, the IRS can tax you as each portion vests, potentially at much higher values later. Filing the election lets you pay tax based on today's typically low value instead. Whether it's the right move for you is a tax question, and depends on your situation.

The 30-day deadline, precisely

The clock starts on the date your shares were issued to you, which is the date on your stock purchase documents, not the date your company was incorporated. Those dates are often different. The election must be postmarked to the IRS within 30 calendar days of the issuance date. The IRS does not grant extensions, and there is generally no way to file late.

Where to find your dates in Clerky

Open your company, go to the Stock section, and find your founder stock purchase. The issuance date shown there is the date your 30-day window is counted from. Clerky also provides 83(b) filing instructions alongside those documents.

An important boundary

Clerky is software that helps you prepare and file paperwork correctly. We are not a law firm or a tax advisor, and we can't tell you whether to make an 83(b) election or what to do if a deadline has passed. For those decisions, talk to a tax professional or a startup attorney. This article explains the mechanics so that conversation is faster.

Related: How do I file my 83(b) election with the IRS? · What is vesting? · When are my founder shares issued?

Draft article, written for this application. The 30-day-from-issuance rule and the no-extensions point reflect widely documented IRS treatment; the exact Clerky navigation labels would be confirmed against the live product before publishing.

05

Each JD responsibility, and my plan for it

Responsibility (from the posting)My planShown in
Write thoughtful, empathetic replies in Help ScoutPrecise, calm, bounded answers that lower stress and stay on the right side of the not-a-law-firm line. Iterate on feedback rather than defend a first draft.the four replies
Write and maintain help-center articles; spot topics for new onesTurn recurring high-stakes questions (like the 83(b) panic) into standing articles founders find before they write in. Draft, test against real tickets, keep them current.the drafted article
Work with engineering to debug software issuesReproduce first, isolate the likely cause, give the customer a workaround, then hand engineering a clean report with account, timestamp and exact repro, not a vague "it's broken."Ticket 03
Develop and manage new ways for customers to complete paperworkUse the recurring failure points I see in tickets to propose clearer flows and self-serve paths, closing the loop between what customers struggle with and how the product guides them.§06
Test new features and bug fixes; convey customer feedbackTest from the founder's mental model, not just the happy path; carry structured, prioritized feedback to product so the common confusions get designed out.§06
Spot trends in customer issues to alert the teamTrack what's spiking and why (a seasonal 83(b) wave, a confusing new step) and raise it early, so one reply becomes a product fix or an article, not fifty repeated tickets.§07
06

The principles I write support by

1 · Lower the stress before adding information

A frightened founder can't absorb a precise answer. One honest, calming line first earns the right to then be exact. Never fake calm, and never skip it.

2 · Lead with the single most useful fact

Find the one thing that changes the customer's picture (the 83(b) clock starts at issuance, not formation) and say it plainly and early, before the caveats.

3 · Name the boundary, then soften it with a real next step

"We're not a law firm" is only abandonment if you stop there. Pair every boundary with something Clerky genuinely can do, today.

4 · Precise beats long

The JD asks for writing that is precise and succinct. I cut every sentence that isn't doing work. Detail-oriented means the dates and the numbers are right, not that the reply is heavy.

5 · Every ticket is a signal

A recurring question is a missing article or a confusing flow. I close the loop: reply now, then feed the pattern to the help center or product so it stops recurring.

6 · Treat feedback as the job, not an interruption

The posting says answers take iterative feedback, often several times a day. I want that. Rewriting a reply until it's right is the craft, not a correction to survive.

07

First 30 / 60 / 90 days

Days 0 to 30, learn the ground truth
  • Learn the product deeply enough to answer without guessing: formation, stock, SAFEs, notes, 83(b).
  • Read a large sample of past tickets to absorb Clerky's voice and the real boundary lines.
  • Take feedback on my drafts eagerly and adjust fast.
Days 30 to 60, carry real volume
  • Own a full share of the queue at Clerky's quality bar, not just easy tickets.
  • File clean, reproducible bug reports to engineering.
  • Draft or refresh two or three help-center articles from the questions I see repeating.
Days 60 to 90, make it compound
  • Surface trends to the team early, before they become ticket waves.
  • Propose one product or flow change that removes a recurring confusion.
  • Be someone the team trusts with the hardest, most sensitive replies.
08

Method & a note on honesty

How this was built

Everything here is written from public information: Clerky's own site and help content, the job posting, and widely documented facts about startup formation and the 83(b) election. The four tickets are invented, not real customer correspondence. The replies and the article are my own writing, drafted for this application to show how I'd work, not copied from Clerky's materials. Any product navigation labels would be confirmed against the live product before I sent them to a real customer. Nothing here is legal or tax advice.

Clerky: clerky.com

Role: Customer Operations & Writing Specialist (Entry Level), remote

Independent worked sample for the Clerky Customer Operations & Writing Specialist role · 2026 · edwardtay.com