Director of Enterprise Accounts
Hybrid in San Francisco, CA (Fully remote work options available)
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 America’s 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, Job, 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.
Our founding engineer and data scientist, Tim Chung, holds a Master’s of Computer Science from UPenn and is midway through a Data Science Master’s 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.
Our head of operations, Job Lawrence, holds a Master’s from Harvard and MBA from the University of Michigan, worked directly alongside Sundar Pichai at early Google for over 10 years where he led strategy and operations, and has run finance, strategy, and ops for startups ranging from the earliest founding stages through Series D funding and beyond.
About You
We're seeking a talented Director of Enterprise Accounts who embodies our values of resilience, execution focus, and mission-driven innovation. The ideal candidate isn't just a relationship manager – they're a strategic partner who sees beyond traditional account management to understand the larger business and human impact of their work.
What Makes You Stand Out
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.
You will be tasked with owning and scaling relationships with Fortune 100 insurance carriers, major financial advisory firms, insurance distributors, and long-term care providers. The goal will be to push beyond traditional account management by becoming a sought-after thought partner who brings innovative insights and best practices to every interaction.
You will work directly with executive stakeholders at some of the largest companies in the industry, requiring frequent travel to conferences and customer sites. Success in this role requires both high-level strategic thinking and attention to detail – from developing executive relationships to creating scalable processes for day-to-day account management.
You will be expected to become deeply knowledgeable about the insurance and long-term care industries through independent research, leveraging AI tools, and extensive stakeholder conversations. This knowledge will enable you to have intelligent, insightful discussions with industry leaders and position yourself as a trusted advisor.
You'll need to balance multiple priorities – from high-touch relationship building to process automation and scalability. We expect you to identify opportunities to use technology (including LLMs and basic scripting) to multiply your impact, while knowing when to roll up your sleeves for hands-on work.
You will be working with our founding US-based team and report directly to our co-founder and COO, Evan Ehrenberg. 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.
Strategic Relationship & Deployment Management: Build and maintain C-level relationships while managing complex implementations. Transform potential friction points into deeper partnerships, navigate client organizations to secure resources and buy-in, and maintain stakeholder enthusiasm through challenging phases. Become their trusted thought partner for industry innovation and implementation success.
Account Growth & Value Realization: Drive account expansion through strategic planning and consistent value delivery. Design and implement comprehensive measurement frameworks, identify key performance indicators, and establish systems to capture relevant data. Transform complex metrics into compelling narratives that demonstrate clear ROI and value creation.
Industry Expert Development: Become a recognized thought leader in the long-term care and insurance space through continuous learning, independent research, and leveraging AI tools to accelerate knowledge acquisition. Use this expertise to identify deployment optimization opportunities and overcome industry-specific challenges.
Process Innovation & Analytics: Create scalable account management processes and leverage technology (including LLMs and basic automation) to multiply your impact. Design and implement sophisticated measurement systems to track deployment success, analyze bottlenecks, and drive continuous improvement.
Executive Engagement & Stakeholder Alignment: Plan and execute high-impact executive meetings, presentations, and social engagements. Build coalitions of internal champions, maintain momentum through challenges, and know when to wine and dine to build authentic relationships that extend beyond the boardroom.
Deployment Success Leadership: Drive customer satisfaction by ensuring successful implementation, adoption, and ongoing value realization. Identify and remove blockers to success, adjust strategies based on performance data, and maintain stakeholder confidence through setbacks.
Cross-functional Leadership: Coordinate effectively with internal teams (product, engineering, operations) to troubleshoot implementation challenges, optimize deployment strategies, and ensure customer needs are met. Transform potential obstacles into opportunities for innovation.
Business Development & Impact Analysis: Identify and pursue strategic expansion opportunities while maintaining strong relationships. Develop and track sophisticated ROI metrics that align with client objectives, quantify business impact, and demonstrate value creation.
Performance Analytics & Optimization: Build comprehensive systems for tracking account health, deployment progress, and strategic initiatives. Analyze complex data sets to identify optimization opportunities, remove implementation bottlenecks, and drive continuous improvement in deployment effectiveness.
Relationship Management & Deployment Excellence:
Proven ability to build and maintain C-level relationships through challenging implementations
Experience managing complex enterprise accounts and technology deployments
Track record of growing strategic partnerships while maintaining momentum
Strong executive presence and ability to turn skeptics into advocates
History of building and leveraging internal champion networks
Technical & Analytics Acumen:
Comfort with technical concepts and ability to discuss them credibly with customers
Experience designing and implementing measurement frameworks
Basic scripting and automation capabilities (or willingness to learn)
Strong data analysis and visualization capabilities
Ability to leverage AI tools and LLMs for research, automation, and analysis
Understanding of enterprise software implementations
Industry & Implementation Knowledge:
Demonstrated ability to quickly learn complex industries
Experience navigating organizational change in regulated industries
Interest in insurance, healthcare, and financial services
Track record of successful enterprise-wide technology implementations
Commitment to becoming a subject matter expert
Experience with enterprise sales and deployment cycles
Strategic Thinking & Value Realization:
Ability to balance high-level strategy with detailed execution
Experience defining and tracking sophisticated ROI metrics
Strong project management and organizational skills
Skills in quantifying and communicating business impact
Data-driven approach to decision making and strategy adjustment
History of optimizing deployments for maximum value creation
Communication & Stakeholder Management:
Outstanding written and verbal communication skills
Experience presenting complex metrics and progress narratives to C-level executives
Ability to translate implementation challenges into clear action plans
Strong negotiation and influence skills
Experience managing expectations across diverse stakeholder groups
Leadership & Change Management:
Experience working with and aligning cross-functional teams
Ability to influence without direct authority
Strong delegation and process creation skills
History of mentoring and developing others
Proven ability to maintain stakeholder confidence through setbacks
Experience building consensus around measurement approaches
Business & Implementation Acumen:
Understanding of enterprise software business models and deployment lifecycle
Experience with complex pricing, ROI analysis, and contract negotiations
Ability to identify and remove implementation bottlenecks
Strong financial analysis and progress measurement skills
Track record of transforming challenges into opportunities
Recommended Experience:
Bachelor's or advanced degree in a technical topic
5+ years of enterprise account management experience
History of managing Fortune 500 relationships and complex implementations at the executive level
Demonstrated track record of exceeding targets and driving measurable ROI
Experience developing and tracking sophisticated success metrics
Willingness to travel frequently (40-50%)
Backed by top VCs: Our largest investor, Insight Partners, is a leading multi-billion dollar global firm renowned for backing innovative companies like Wiz, Calm and Monday, 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 March this year 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 run multiple departments, lead large teams, and gain diverse experience that will propel your career forward.
Impact: Play a key role in shaping the future of our company and making a tangible difference for families across America and the world.
Dynamic Environment: Work in a fast-paced, innovative startup culture that encourages creativity and out-of-the-box thinking.
Equal Opportunity Employer
We are an equal opportunity employer and value diversity at our company. We do not discriminate on the basis of race, religion, color, sex, gender identity, sexual orientation, age, marital status, veteran status, or disability status.
How to Apply
If you’re ready to take on a challenging and rewarding role, we want to hear from you! Please send your resume and a brief cover letter explaining why you’re the perfect fit for this position to careers@joinwaterlily.com
