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Waterlily Caregiving Inc.
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Job Type: Full-Time
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.
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.
This is an unusually high-ownership role. It's important to be equally clear about what the opportunity is not.
You want a narrow lane with a fixed job description.
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 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.
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.
Originally posted on Himalayas
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