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We are seeking a talented generalist operator with the raw talent and grit to join our team and grow into a leader and innovator in sales, marketing, customer support, and management operations that drive 10x value by leveraging automation, LLMs, and offshoring to run multiple departments. We expect you to have the drive, and will give you the tools to lead the industry with novel best practices. Versatility is required as you will need to wear many hats and adapt to the company's needs on an ongoing basis.
An ideal candidate does not necessarily have a long resume, but can show a sharp growth trajectory with the ambition to push further. We are looking to develop someone into an industry leader without the constraints of needing to unlearn how it's been done. You will be given the opportunity and the mission to drive new best practices that any company or startup would be envious of.
About Us
Waterlily uses AI to help families prepare for the largest financial and medical event in their lives, long-term care (LTC). Through comprehensive care planning and optimization, Waterlily is bending Americas multi-trillion dollar LTC cost curve.
Our Team & Culture
We've built a high-performance team culture based on three core principles:
Mission-Driven Excellence
We're deeply committed to transforming how families prepare for long-term care
Every team member genuinely believes in our mission and understands its importance
We prioritize work that drives meaningful impact for our customers and company
Be a Potato: Growth & Resilience
We embrace challenges and adapt quickly - like potatoes that grow under any circumstances
We make decisions swiftly while remaining thoughtful and open to iteration
We focus on execution and results rather than just effort, recognizing that input doesn't necessarily equal output
We value team members who show unlimited potential for growth and understanding
Radical Transparency & Support
We practice direct, honest communication while maintaining empathy and respect
Feedback flows freely in all directions - from intern to leadership and back
We begin meetings with brief check-ins to understand each other's context
We create safe spaces for vulnerability and authentic collaboration
We maintain high standards while supporting each other's growth and wellbeing
Our team comprises some of the brightest, most ambitious, playful, and friendly people you'll meet. You'll be working closely with our founding Waterlily team, including Lily, Evan, and Tim, and have direct access to a support team in the Philippines.
️ Lily Vittayarukskul , our CEO, is a patented inventor who started college at 14, attending UC Berkeley, was working at NASA when she was 16, and lead product and engineering at IoT medical device startups for years before founding Waterlily.️
Evan Ehrenberg , our COO, is a member of Forbes 30 Under 30, started college at 11, also attending UC Berkeley, and then continued on to his Ph.D. in computational neuroscience at MIT at 16 before dropping out at 21 to found Clara Health, a clinical trials SaaS platform and B2B2C marketplace, which he sold 7 years later before joining Waterlily.
Tim Chung , our founding engineer and data scientist, holds a Masters of Computer Science from UPenn and is midway through a Data Science Masters at Georgia Tech. Tim excels in a trio of roles: data scientist, machine learning engineer, and full-stack software engineer. At his previous companies, he led teams to launch pioneering machine learning models.
How We Work
We optimize for remote-first collaboration while maintaining high productivity
We emphasize contextual decision-making and practical solutions
We prioritize deep work and focused execution over unnecessary meetings
We consistently validate that we're working on the highest-impact initiatives
We maintain a healthy, growth-oriented mindset while pushing for exceptional results
We're looking for teammates who share our values of integrity, empathy, and intelligent hard work - people who can see beyond their immediate role to understand both company needs and customer impact.
About You ⭐
Growth Mindset & Adaptability
You're a "potato" - able to grow and thrive under any circumstances
You have a track record of rapidly learning complex industries and business domains
You proactively dive deep into industry knowledge, leveraging tools like LLMs to accelerate your learning
You're comfortable with ambiguity and can navigate complex enterprise relationships with confidence
Innovation & Execution
You have a history of building strategic relationships that challenge traditional approaches
You can point to specific examples where you've used automation or AI to multiply your impact
You focus on delivering value while building long-term partnerships
You have experience or strong interest in using technology to scale your effectiveness
Leadership & Relationship Building
You give and receive direct feedback with grace and professionalism
You can build deep, trusted relationships with enterprise executives
You're equally comfortable in formal boardrooms and informal social settings
You naturally build trust through consistent execution and thoughtful relationship management
Mission Alignment
You're drawn to meaningful work that impacts families' lives
You understand that sustained high performance requires maintaining personal wellbeing
You're excited about becoming a thought leader in the long-term care industry
You're genuinely passionate about transforming how families prepare for long-term care
The Ideal Background
While we value potential over experience, you likely have:
Demonstrated ability to manage and grow enterprise relationships
Experience navigating complex sales cycles and stakeholder relationships
Track record of improving team efficiency through process innovation and automation
History of taking initiative and driving results without extensive oversight
Comfort with technical concepts and ability to do light scripting/automation
Experience managing both high-level strategic relationships and detailed execution
We're not looking for someone who's done it all before we're looking for someone who has the raw talent and drive to help us pioneer new approaches to enterprise relationship management. If you're excited about pushing boundaries, learning rapidly, and making a real difference in people's lives, we want to talk to you.
About The Role
You will be tasked with owning and scaling mission-critical operations within customer support, sales, marketing, and general operations management. The goal will be to often push beyond industry best-practices by innovating new strategies that leverage LLMs and offshore teams to achieve company-defining results for a fraction of the time and cost of what other companies have previously achieved.
You will be working with our founding US-based team and report directly to our co-founder and COO, Evan Ehrenberg, and you will grow to manage a team of 40+ in the Philippines. You will collaborate on new ideas and implement quickly to test and iterate. Many ideas will not work and will be thrown away. Many ideas will need to be imperfect so that we can implement them faster. Everything will be iterative, no challenge will be too ambitious.
You will be challenged to produce meaningful results every week. It will likely take you more than 40 hours per week to drive industry-leading results. We do not think that 80 hour weeks are effective, and we expect you to limit yourself to 50-60 hour work-weeks. If you want to push harder we will urge you to reflect on ways to be more effective with your time so that you can dedicate your remaining time to benefit your mental and physical health.
We will be in the trenches with you, and together we will create one of the most impactful companies that will help families prepare for what has historically been one of the most devastating times in their lives so that they can face long-term care with confidence and calm.
Key Responsibilities ️
Customer Success : Your mission is to surprise and delight our customers through product and customer support initiatives that go above and beyond to make Waterlily their favorite company to work with.
Marketing & Sales Operations : Think creatively to implement non-traditional growth hacking strategies that outperform paid marketing and elevate our brand.
Process Automation : Super-charge your impact by leveraging large offshore teams, LLMs, and no-code/low-code solutions to automate workflows to scale low-cost strategies that outperform traditional approaches.
Team Management : Oversee and coordinate the efforts of an offshore team of over 40 individuals.
Content Creation : Craft and fine-tune communications to users and industry executives to combine scale with personalization and high standards of communication quality.
Key Skills & Qualifications
Voracious Learner: Eager to rapidly learn about new industries and departments with the passion and grit to dive deep in specific verticals to gain sufficient context to push the boundaries and improve upon historic best-practices.
Highly Motivated and a Self-Starter : Ready to take initiative and drive projects forward with minimal supervision or structure.
Adaptability and Problem-Solving : Thrive in a fast-paced, dynamic environment by quickly adapting to new challenges and finding innovative solutions with minimal direction.
Extraordinary Copywriting and Email Writing : Ability to create clear, persuasive, and engaging content that resonates with audiences ranging from families to industry executives.
No-Code/Low-Code Proficiency : Experience with tools like Zapier, Airtable, Google Apps Script, PhantomBuster, or similar to automate tasks and streamline processes.
GenAI Prompting : Strong skills in creating and tuning GenAI prompts to reliably produce high-quality results.
Strong Communication Skills : Both written and verbal, with the ability to convey complex ideas simply.
Why Join Us?
Backed by top VCs : Our investors are renowned for backing innovative companies and helping them grow to become industry leaders.
Customers Love Us : Check out some of our latest success case studies and customer testimonials and see why our customers love us so much.
Industry Giants Onboard : After launching in early 2024 we've already closed 3 Fortune 100 customers, 4 insurance carriers, one of the largest LTC providers in the Midwest, and one of the largest insurance distributors in the US.
Direct Mentorship and Development from our Co-Founders : Receive guidance and resources to develop your skills and become a 10x operator.
Growth Opportunities : Learn to operate multiple functions and gain diverse experience that will propel your career forward.
Dynamic Environment : Work in a fast-paced, innovative startup culture that encourages creativity and out-of-the-box thinking.
Impact : Play a key role in shaping the future of our company and making a tangible difference for families across America and the world.