Joseph's Interview Summary
Interview Overview
Position: Operations Generalist
Company: Waterlily
Interview Duration: ~12 minutes
Compensation Discussed: $50-60/hour (standard), willing to accept $20/hour
Career Background
Early Career
Started at 14: Hospitality industry at 2 and 3 Michelin-starred restaurants Focus: Creating unforgettable customer experiences Cannabis Industry Experience
First Role: Operations Associate → Director of Operations at cannabis M&A firm Achievement: Built systems managing $30M in retail assets during rapid growth Second Role: Head of Operations at SFEG (mission-driven M&A with shared ownership model) Expanded Skills: Marketing, legal, and financial management Entrepreneurial Experience
Founded NicerCo: Retail cannabis brand with community profit-sharing model Goal: National scaling with social impact Outcome: Wound down in 2021 due to COVID industry disruption Tech Industry Transition
Tradery (AI Trading Startup): First operations hire → COO over 5 years Built all departments and teams around initial algorithm Pivoted to hedge fund tech solutions Scaled down to engineering-focused team 24-Hour Inspections: Director of Operations & Chief of Staff Scaled remote AI-driven inspection infrastructure Core Competencies
1. Executive Support
Internal systems for calendar optimization (time-blocking, prioritization, automation) Email management and response systems Weekly executive team meeting facilitation Strategy workshop design and co-facilitation 3-day offsite planning (OKRs, team-building, retrospectives) 2. Recruiting & Management
Managed 6 legal firms, 2 design firms, accounting firms Recruited full product teams and 3 complete workforces (10-30 headcount) Built interview tools, onboarding architectures, and SOP training systems 3. Business Operations
Owned 100+ projects personally Managed multi-million dollar initiatives 10 end-to-end business development deals Supported 5 go-to-market cycles Managed accounting/finance for 3 businesses (invoicing, payroll, budgeting, governance) Work Methodology
Organization System
Quarterly Planning: Strategic priority mapping with data support OKR Framework: Visible targets in project management software Task Management: Granular breakdown from OKRs to daily tasks Time Blocking: Every minute scheduled for highest-priority work Daily Adjustment: Using Sunsama for tactical priority shifts Weekly Retrospectives: Green/yellow/red scoring for continuous improvement Problem-Solving Framework: 131 Protocol
Dissect: Thoroughly analyze problem (people, technology, domain) Three Solutions: Logic-based options including "do nothing" One Recommendation: Best solution selection AI Enhancement: Converted to workflow for technical problems Notable Examples
Success Story: Tradery Fundraising Pivot
Challenge: Mid-raise business model pivot due to tech constraints Solution: Shifted priorities between fundraising and recruiting Result: Successfully completed fundraise with modified narrative Failure Example: 24-Hour Inspections Conference
Situation: Last-minute conference prep with unrealistic timeline Issues: Incomplete deliverables, frustrated CEO, demoralized team Better understand priority of deliverables Push back on unrealistic timelines Set realistic expectations Conflict Resolution: NicerCo Ownership
Problem: Uneven contributions despite equal ownership Solution: One-on-one facilitated dialogues, mission recentering Outcome: Restructured agreements around fairness Future Approach: Set explicit contribution expectations upfront Motivation & Fit
Personal Drivers
Impact-Focused: Only pursuing meaningful work Self-Actualization: Physical/mental health, purposeful work, continuous learning Coaching Culture: Loves both coaching and being coached Why Waterlily
"Potato" Mindset: Extreme adaptability and growth orientation Relevant Experience: Team building, systems, protocols, frameworks Mission Alignment: Deep connection to helping families with LTC planning Team Quality: Attracted to "rare collection of awesome and deep talent" Communication Philosophy
Understanding stakeholder needs and motivations Adapting to preferred communication styles and platforms Tools: User manuals, RACI charts, Slack automation Principle: Share only essential, actionable information to relevant parties Closing Notes
Gratitude Expression
Acknowledged high competition for role Thanked team for raising LTC awareness Personal impact: Family now using Waterlily for 86-year-old grandmother Demonstrated genuine mission alignment beyond just job seeking Key Differentiators
Extensive startup experience across multiple industries Built and scaled operations from ground up multiple times Strong systems thinking and automation mindset Deep commitment to meaningful work Proven ability to wear many hats and adapt quickly Experience managing large offshore teams Track record of both successes and learning from failures Potential Questions
Mission & Culture Alignment
Core Mission Questions
Why Waterlily specifically? What drew you to our company? How does our mission to help families prepare for long-term care resonate with you personally? Tell me about a time you worked on something that had meaningful impact on people's lives What does "mission-driven excellence" mean to you? How do you stay motivated when working on complex, long-term problems? "Be a Potato" Mindset Questions
How do you handle uncertainty and rapid change? Tell me about a time you had to adapt quickly to completely new circumstances Describe a situation where you had to learn something completely new under pressure How do you thrive in ambiguous situations without clear direction? Give me an example of when you had to pivot your approach mid-project Radical Transparency Questions
How do you give difficult feedback to team members? Tell me about a time you received constructive criticism - how did you handle it? Describe a situation where you had to be completely honest about bad news How do you build trust with people you've never met in person? What's your approach to sharing both successes and failures with stakeholders? Operations & Scaling
Team Management Questions
How would you manage and coordinate a team of 40+ people in the Philippines? Tell me about your experience managing remote, multicultural teams How do you ensure quality and consistency across different time zones? Describe your approach to onboarding new team members in different countries How do you handle performance issues with offshore team members? Process & Automation Questions
Walk me through how you'd automate a complex, multi-step workflow How would you scale our customer support from 50 to 500 inquiries per week? Tell me about a time you used automation to solve a business problem How do you balance automation with human touch in customer interactions? Describe a process you've built that significantly improved team efficiency Systems & Infrastructure Questions
How do you ensure data quality and accuracy in automated systems? Tell me about a time you had to build something from scratch with limited resources How would you design a system to track and improve team performance? Describe your approach to documenting processes for global teams How do you maintain operational excellence while moving quickly? Growth & Strategy
Business Development Questions
How would you help us grow from 500 to 5,000 financial advisors? What creative growth strategies would you try for Waterlily? Tell me about a time you identified and executed on a growth opportunity How would you approach partnerships with major insurance companies? Describe a marketing campaign or initiative you've led Customer Success Questions
How would you ensure our advisors are successful with our platform? Tell me about a time you turned an unhappy customer into an advocate How do you measure and improve customer satisfaction? Describe your approach to gathering and acting on customer feedback How would you design an onboarding process for new advisors? Innovation Questions
What's a creative solution you've implemented that others hadn't thought of? How do you balance innovation with execution and results? Tell me about a time you challenged the conventional way of doing things How would you use AI/LLMs to improve our operations? Describe a time you built something that became a best practice for others Leadership & Communication
Stakeholder Management Questions
How do you build relationships with enterprise executives? Tell me about a time you had to manage conflicting priorities from different stakeholders How do you communicate complex technical concepts to non-technical audiences? Describe your approach to managing up, down, and across an organization How do you ensure all stakeholders stay aligned on project goals? Problem-Solving Questions
Tell me about the most complex problem you've had to solve How do you approach problems when you don't have all the information you need? Describe a time when your initial solution didn't work - what did you do? How do you prioritize when everything seems urgent? Walk me through your decision-making process for high-stakes situations Execution Questions
Tell me about a time you had to deliver results under tight deadlines How do you ensure quality while moving at startup speed? Describe a project where you had to coordinate multiple moving parts How do you handle competing priorities and limited resources? Tell me about a time you had to make a decision with incomplete information Industry & Technical Knowledge
Long-Term Care Industry Questions
What do you see as the biggest challenges in long-term care planning? How familiar are you with the financial services/insurance industry? What do you think about the current tools available for LTC planning? How would you explain Waterlily's value proposition to a skeptical financial advisor? What trends do you see in how families approach retirement and aging? Technology & Tools Questions
What's your experience with no-code/low-code automation tools? How have you used AI or LLMs to improve your work? Tell me about your experience with CRM systems and sales operations How comfortable are you with data analysis and reporting? What project management and collaboration tools do you prefer? Scenario-Based Questions
Crisis Management
Our AI platform is showing errors for 30% of users during peak hours. Walk me through your response A major enterprise client is threatening to cancel due to a service issue. How do you handle it? We've received negative press coverage about our AI predictions. What's your communication strategy? Resource Allocation
You have a $25,000 budget to maximize our presence at a major industry conference. How do you use it? We need to choose between hiring 2 more US team members or 8 more offshore team members. How do you decide? Our customer support is overwhelmed but we can't hire more people for 3 months. What do you do? Strategic Decisions
A Fortune 500 company wants to partner with us but requires significant platform changes. How do you evaluate this? We're considering expanding to Canada vs. focusing on more US growth. How would you analyze this decision? Our biggest competitor just launched a similar AI feature. What's your response strategy? Behavioral & Situational
Failure & Learning Questions
Tell me about your biggest professional failure and what you learned Describe a time when you were completely wrong about something important How do you handle situations when you don't know the answer? Tell me about a project that didn't go as planned Describe a time you had to admit you made a mistake to your team Collaboration Questions
Tell me about a time you had to work with someone whose working style was very different from yours Describe a situation where you had to influence someone without formal authority How do you handle conflicts within your team? Tell me about a time you had to coordinate with multiple departments to achieve a goal Describe your approach to building consensus among diverse stakeholders Work Style Questions
How do you stay organized when juggling multiple priorities? Tell me about your approach to time management How do you ensure you're working on the highest-impact activities? Describe your ideal work environment and communication style How do you maintain high performance over 50-60 hour work weeks? Questions About Joseph Specifically
Career Transition Questions
Walk me through your career progression from hospitality to cannabis to tech How did you develop expertise in operations across such different industries? What skills have transferred well across your various roles? Why did you choose to move from founding your own company to joining startups? How do you apply lessons from the restaurant industry to tech operations? Specific Experience Questions
Tell me more about managing that $30M in cannabis assets How did you handle the pivot at Tradery during fundraising? What did you learn from winding down NicerCo during COVID? Describe your experience as COO at Tradery - what did you build there? How did your role evolve at 24-hour inspections? Questions for You to Ask Them
About the Role
Confirm operations generalist role vs generalist. What does the rest of the process look like from here? Are there a lot of candidates for the role?? What would success look like in this role after 90 days? 6 months? 1 year? What are the biggest operational challenges you're facing right now? How do you see this role evolving as the company scales? What skills or background would make someone wildly successful in this position? What's the most important thing I should accomplish in my first month? About the Team & Culture
Tell me about how culture is currently reinforced by leadership. Can you give me an example of how "radical transparency" plays out day-to-day? How does the team coordinate between US and offshore operations? What does the feedback culture look like between different levels of the organization? How do you maintain the "potato" mindset as the company grows? What's the biggest cultural challenge you've faced while scaling? About the Business
What are the primary priorities wrapping this quarter and how do you run planning and execution cycles? What operational bottlenecks are you most concerned about as you scale? Which competitors do you watch most closely and why? What's the most surprising thing you've learned about advisor behavior since launching? How do you see AI evolving in the LTC planning space over the next 2-3 years? What would make this role a 10x success from your perspective? About Growth & Future
What's your vision for the offshore team's role in the company's growth? How do you balance the 50-60 hour expectation with sustainable team growth? What learning and development opportunities exist for this role? Where do you see the biggest opportunities for operational innovation? How do you envision the company in 2-3 years? Strategic Insights & Positioning
Executive Summary
This prep guide positions Joseph as a uniquely qualified Operations Generalist who understands Waterlily's mission, market opportunity, and operational needs at a deep level.
1. Unique Insights About Waterlily's Business
The $6 Trillion Opportunity
Quick Recall:
$6T market failure: 70% need LTC, only 10% prepared $240K average destroys family wealth Your angle: "Not software—category creation. Transforms fear into empowerment." The B2B2C Genius
Quick Recall:
Advisors pay $250/month → serve their clients → everyone wins Distribution + trust solved simultaneously Your angle: "Did this at 24-Hour Inspections: made lenders heroes to borrowers. Created flywheel—happy borrowers → lenders send more business → we improve → lenders look even better. Same opportunity here." The Data Network Effect
Quick Recall:
500M+ data points = unbeatable moat Every user improves predictions for all Your angle: "From Tradery: operational excellence → better data → better AI → happier customers → growth flywheel." Crossing the Chasm Strategy
Quick Recall:
Financial advisors = perfect beachhead (specific, reachable, desperate for differentiation) Wedge into $6T market through trusted intermediaries Fortune 100 wins prove enterprise readiness Your angle: "Classic Geoffrey Moore playbook—dominate financial advisors as beachhead, then expand to insurance carriers, then employers. At NicerCo, we tried to boil the ocean. Here, you're methodically conquering one beach at a time. Operations must support both current beachhead dominance AND prepare for mainstream market infrastructure." 2. Strategic Questions That Show Deep Thinking
About Scale & Operations
"With 40+ offshore team members and rapid growth, what's the biggest operational bottleneck preventing Waterlily from scaling even faster?" Shows you think in systems and constraints Opens discussion about your experience scaling teams "How are you balancing automation with the high-touch service that enterprise clients expect? Where do you see the biggest opportunities for AI-driven efficiency?" Demonstrates understanding of their "novel best practices" philosophy Lets you discuss your automation expertise About Market Strategy
"I noticed you've landed Fortune 100 clients incredibly fast. What operational infrastructure needs to be built to support enterprise accounts while maintaining startup speed?" Shows you understand enterprise vs. startup tensions Positions your multi-company experience as valuable "With expansion into disability and Medicare planning on the roadmap, how do you envision the operations team preparing for multi-product complexity?" Forward-thinking about product evolution Shows you can think beyond immediate role About Culture & Team
"The 'Be a Potato' philosophy really resonates with me. Can you share an example of how this shows up in day-to-day operations?" Demonstrates cultural fit Opens door to share your adaptability stories "With founders who started college at 11 and 14, I imagine the pace of learning here is intense. How do you support team members in keeping up while maintaining work-life balance?" Shows awareness of unique team dynamics Aligns with their 50-60 hour week philosophy 3. Highlights to Emphasize (Mapped to Their Needs)
Your "Potato" Credentials
Their Need: Extreme adaptability and growth mindset Your Story:
Started in Michelin restaurants at 14, pivoted to cannabis, then to AI/tech Built operations from zero at 3 different companies "I've literally built playbooks for industries that didn't have playbooks" Enterprise + Startup Experience
Their Need: Managing Fortune 100 relationships while moving fast Your Highlight:
Managed $30M in assets while in hypergrowth at cannabis firm Scaled Tradery from startup to hedge fund clients "I know how to wear a suit in the boardroom and roll up sleeves in Slack" Offshore Team Management
Their Need: 40+ Philippines team coordination Your Highlight:
Built and managed 3 different remote workforces (10-30 people) Created SOPs and training systems that scale "I've learned that great offshore management is 20% process, 80% culture" AI/Automation Expertise
Their Need: Leveraging LLMs and automation for 10x impact Your Highlight:
Converted problem-solving frameworks into AI workflows 5 years at AI trading startup (Tradery) "I don't just use AI tools - I think about how to systematize human judgment" Mission Alignment
Their Need: Genuine belief in transforming LTC planning Your Highlight:
Founded NicerCo with community profit-sharing mission Only pursuing impact-focused roles "My 86-year-old grandmother is now using Waterlily because of this application" 4. Operational Ideas to Share (Show Don't Tell)
Quick Win: Advisor Onboarding Automation
"I'd love to build an automated advisor onboarding sequence that combines personalized video messages, AI-generated welcome packets based on their client base, and automated calendar scheduling for success calls. Could reduce time-to-value from days to hours."
Systems Thinking: The "Waterlily Playbook Library"
"With your rapid growth, I imagine knowledge management is crucial. I'd create a living playbook library - templatized but customizable processes for every function, powered by AI that learns from what works. Think 'Uber's launch playbook' but for LTC planning."
Revenue Operations: Expansion Revenue Engine
"Your 15% expansion rate is strong but could be stronger. I'd design an automated system that identifies expansion opportunities based on usage patterns, triggers personalized outreach, and tracks what messaging drives upgrades."
Culture Innovation: "Potato of the Month"
"To reinforce the 'Be a Potato' culture, create a peer-nominated program celebrating extreme adaptability. Winners share their story in an all-hands, creating a library of adaptation examples for new hires."
5. Addressing Potential Concerns
Concern: "You've jumped between industries a lot"
Your Response: "Each transition taught me how to learn fast and build from first principles. In AGI's future, industry expertise becomes less valuable than the ability to rapidly understand new domains and build novel solutions. My varied background is my superpower."
Concern: "Do you have enough SaaS experience?"
Your Response: "While Tradery was B2B SaaS for hedge funds, I've also studied Waterlily's model deeply. Your $250/seat pricing, 58% monthly growth, and 3% churn suggest strong product-market fit. I'd love to discuss specific ideas for reducing that churn further."
Concern: "This role requires 50-60 hour weeks"
Your Response: "I appreciate the transparency. I've worked those hours when building companies, but I've learned it's about energy management, not time management. Your focus on effectiveness over hours aligns perfectly with how I work best."
6. Closing Strategy
The Vision Close
"Based on everything we've discussed, I see three ways I could immediately impact Waterlily:
Build operational infrastructure that supports your next 10x growth phase Create novel automations that make your team superhuman, not replaced Develop playbooks that turn your unique approaches into repeatable excellence I'm not looking for a job - I'm looking to help build the company that makes my grandmother's final years dignified rather than devastating. When can I start?"
The Learning Close
"This conversation reinforced why Waterlily is where I want to be. You're not just disrupting an industry - you're creating a new category. I have a few ideas about offshore team optimization I'd love to pilot in my first 30 days. What's the most important operational challenge I could help solve first?"
The Mission Close
"You know what sealed it for me? When my family started using Waterlily for my grandmother after seeing this job posting. That's when I knew this wasn't just another startup - you're solving a problem every family faces. I want to help scale that impact to millions. What questions can I answer to help you feel confident I'm the right person for this mission?"
7. Final Preparation Checklist
Technical Prep
[ ] Test your video/audio setup [ ] Have Waterlily's website open in a tab [ ] Pull up your automation examples [ ] Have specific metrics ready (your achievements in numbers) Mental Prep
[ ] Review their team backgrounds (Lily, Evan, Tim, Job) [ ] Practice pronouncing "Vittayarukskul" [ ] Prepare 2-3 specific Waterlily product features to reference [ ] Have a 60-second version of your story ready Energy Management
[ ] Do something physical beforehand (embody the "potato" energy) [ ] Review your grandmother story (connect to mission) [ ] Visualize yourself already in the role [ ] Remember: They need you as much as you want this Post-Interview
[ ] Send thank you within 2 hours [ ] Include one specific idea discussed [ ] Reiterate mission alignment [ ] Propose concrete next steps Remember: You're Not Interviewing, You're Consulting
Approach this interview as if you're already their Operations Generalist, solving problems together. Every question is an opportunity to demonstrate how you think, not just what you know.
The fact that your family is now using Waterlily because of your application? That's not just a nice story - it's proof that you understand their mission at a visceral level.
Go show them what a true "potato" can do. 🥔
The six standard ADLs are generally recognized as bathing, dressing, toileting, transferring (getting in and out of bed or chair), eating, and continence.
People don't remember what you do or what you say they remember how you make them feel. If you change what gets measured, you change what gets done People like us do things like this. I find it much easier to sell things that are important for society and that matter to me deeply.
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