Skip to content
CV Rocket
Get started
How it worksThe enginePricingBlogContactSign in

Open nowFirst seen 5 days ago

Office of the Founders

Waterlily Planning5 open roles

Where
San Francisco, California, United States, Remote
Work mode
Remote
Get the CV for this job

From $25 per CV, paid once. No subscription.

Your applicationOpen nowOffice of the FoundersWaterlily Planning · San Francisco, California, United States, Remote

  1. YouYes, apply to this one.

  2. CV RocketCV written for this posting.

  3. 25 readersRecruiter, hiring manager, skeptic. Round after round.

  4. CV RocketApplied on Waterlily Planning's own form.

The reply lands in your private mailbox

3×more interviews than doing it yourself with ChatGPT.

The clock on this job

Early applications get read.

12.3% of postings close within 7 days. Measured by our own scanner across the market.

Share of postings closed within
  1. 2.1%1 day
  2. 4.5%3 days
  3. 12.3%7 days
  4. 19.3%14 days
  5. 35.6%30 days
  6. 58.1%60 days
This job: first seen 5 days ago

The posting

Role Overview

  • Job Type: Full-Time
  • Role Type: AI-Native Founders Office / GTM / Executive Operations / Business Operations / Special Projects / Chief of Staff
  • Ideal Experience Level: 2–7 years; exceptional candidates outside this range are encouraged to apply
  • Location: Remote, with some expected travel

Waterlily is hiring unusually sharp, technical, high-agency operators who will work directly with our founders and leadership to solve high-leverage problems across growth, revenue, finance, hiring, culture, legal, investor work, operations, and internal AI systems (Office of the Founders).

This is not an executive assistant role. It is not a traditional business operations role. And it is not a junior Chief of Staff role with a better title. It is a new kind of role for the AI-native era: a technical, high-agency generalist embedded with senior leaders to make the company dramatically faster.

You will sit close to leadership, see the company's most important problems early, and be expected to build solutions fast. One day you might prototype an internal AI tool that saves the operations team 30 hours per week. The next day you might analyze advisor activation, build a GTM model, improve a hiring process, automate investor reporting, draft a strategy memo, or create a workflow that helps a non-technical team specify exactly what they need before engineering gets involved.

The center of gravity is GTM and company leverage. You should constantly be asking: where are we losing customers, revenue, speed, quality, or focus, and what can I build, automate, analyze, or fix this week to move the company forward?

The strongest candidates have rigorous technical or quantitative foundations, whether through computer science, engineering, data science, operations research, financial engineering, applied math, statistics, economics, or similarly demanding experiences. You may have experience in consulting, banking, finance, startups, product, data, or engineering. What matters most is raw intelligence, speed, taste, grit, communication, AI fluency, and demonstrated ability to make things.

This is a career-accelerating role for someone who wants unusual exposure and responsibility. You will be in the room for meaningful company decisions, work directly with our CEO and COO, get tough deadlines, and learn by doing real work that matters.

Who We're Looking For

  • Experience in a high-performance environment such as consulting, investment banking, private equity, strategic finance, startup operations, product, data, engineering, or a similarly intense setting.
  • Strong preference for a technical or quantitative degree or equivalent demonstrated capabilities in computer science, engineering, data science, operations research, financial engineering, applied math, statistics, economics, or similar.
  • Demonstrated competency in making things and automating things. You have built projects, scripts, tools, automations, prototypes, dashboards, agents, websites, apps, analyses, or workflows that actually worked.
  • Deep AI-native working style. You do not just "use ChatGPT." You use AI tools to build, analyze, automate, prototype, research, write, debug, synthesize, and move faster every day.
  • Ability to build lightweight tools or prototypes using some mix of Python, JavaScript, SQL, spreadsheets, APIs, no-code tools, AI coding tools, product prototyping tools, and data platforms.
  • Strong analytical horsepower. You can build a model, interrogate assumptions, analyze a funnel, understand unit economics, and explain what matters.
  • Strong GTM instincts. You care about customer growth, revenue, conversion, retention, activation, reactivation, CAC, payback, funnel dropoff, and the practical mechanics of moving numbers.
  • Excellent written communication. You can write a memo, investor update, recruiting note, project spec, growth analysis, operating plan, or executive summary that is crisp and useful.
  • Strong people judgment. You can work with founders, operators, financial advisors, insurance professionals, executives, engineers, lawyers, candidates, investors, and vendors without losing context or trust.
  • Comfort with sensitive information. You can handle customer, company, legal, financial, recruiting, investor, and operational information with maturity and discretion.
  • High agency and low need for structure. You do not wait for someone to define the perfect project. You find leverage and go create it.
  • High-conviction interest in Waterlily. This role is intense, ambiguous, and close to leadership. It is best for someone who genuinely wants to be here and sees this as a chance to put their career on a much faster track.

Who This Role Is NOT For

This is an unusually high-ownership role. It's important to be equally clear about what the opportunity is not.

This role is probably not a good fit if:

  • You want a narrow lane with a fixed job description.
  • You prefer advising over doing.
  • You cannot figure out what to do to move the needle and operate without much direction.
  • You are not deeply curious about AI tools.
  • You need engineers or analysts to answer every first-pass technical or data question.
  • You are uncomfortable with growth, revenue, or commercial pressure.
  • You optimize for looking strategic instead of creating measurable leverage.
  • You want prestige without intensity.
  • You do not want to work closely with leadership in a high-speed environment.
  • You require constant supervision, struggle to communicate proactively, or find it difficult to create accountability and momentum in a remote working environment.
  • You are unwilling to travel when important company priorities require in-person collaboration.

Compensation, Benefits & Growth

  • Salary: Flexible
  • Early-Stage Equity: Competitive
  • Health Insurance: Medical, dental, and vision benefits
  • Additional Perks: In-person retreats, meal stipends, AI tooling budget, learning stipend, home office support
  • Time Off: Flexible, unlimited vacation policy
  • Work Hours: Flexible, with responsiveness around high-priority company moments
  • Work Setup: Remote, with some expected travel
  • Impact: Work directly on the highest-leverage problems at a company trying to transform how families prepare for aging and long-term care.
  • Autonomy and Learning: Operate across growth, finance, hiring, AI systems, investors, legal, product, culture, and operations.
  • Growth Opportunities: This role can grow into larger roles across GTM, business operations, product operations, strategy, or company-building.
From $25, paid onceGet the CV for this job

What happens when you press

One press. We do the rest.

  1. A CV for this posting

    Written against Waterlily Planning's own wording, from every piece of relevant proof in your profile.

  2. 25 readers review it

    Recruiter, hiring manager, skeptic and more read every draft, round after round. You get the best round.

    The review screen in CV Rocket: how each CV was read, round by round.

  3. We apply on Waterlily Planning's form

    Our application engine gets through the hardest forms there are. Where a question needs you, AI suggests the best answer. Don't want us applying from our IP addresses? Use our Chrome extension: we apply straight from your own browser.

    An application in CV Rocket: every answer filled in on the employer's form.

  4. Every reply, sorted

    Waterlily Planning's answer lands in your private mailbox, and we classify it on arrival: interview, question, rejection.

    The CV Rocket inbox: each employer reply classified as an interview, an action or a rejection.

  5. Reply with AI

    AI helps you write the email, checks it and sends it. We show you whether the recruiter read it.

  6. The interview in your calendar

    Full integration with your calendar. The invitation goes straight in.

    An interview invitation in the CV Rocket inbox, added to the candidate's calendar.
Get the CV for this job

From $25 per CV, paid once. No subscription.

Why it works

3×

more interviews than doing it yourself with ChatGPT.

ChatGPT writes a CV and never learns what happened to it. We see every reply. For each CV we know:

  • How it was written, and how the review scored it
  • When we applied, and how long after the posting went up
  • Which posting, which company, which city
  • Who got the interview, and who heard nothing

That is how we know which CVs get called.

Get the CV for this job

From $25 per CV, paid once. No subscription.

The numbers game

More applications. More interviews.

Every application goes out with its own CV, written for that posting and paid once. Send enough of them and the law of large numbers finds you the job.

Get the CV for this job
By hand5–10
With CV Rocket100
applications a day

Nearby

Live postings like this one

Same employer first, then the same role elsewhere.

Before you press

Straight answers

Get the CV for this job

From $25 per CV, paid once. No subscription.

What if my background isn't good enough?

We make the most of the background you have. The CV uses every piece of relevant proof your profile holds, and one of the 25 readers reads your whole profile and flags what the CV left out.

Do you really apply for me?

Yes, on the employer's own form, the hardest ones included. Where a question needs you, you answer it right there and AI suggests the best answer. Don't want us applying from our IP addresses? Use our Chrome extension: we apply straight from your own browser.

Is it a subscription?

No. You pay once per CV, from $25. Every application goes out with its own CV, written for that posting.

One job. One CV.
Paid once.

Pick the posting you want. We write for it, apply for you and catch the reply.

Get the CV for this job

From $25 per CV, paid once. No subscription.