Family Success Lead - FlightPlan
Location: San Francisco, CA
Starting: July 2026
Benefits: 20 days PTO, 401k, health, dental, vision insurance
Quick Facts
Company stage: Seed
Funding raised: $6.8M
Number of Employees: 12
About Curious Cardinals
Curious Cardinals is a mentorship marketplace and learning platform helping K-12 students find their passions, build confidence, and develop timeless skills for an AI-driven future. We've grown to support thousands of students globally through a network of 1,000+ mentors from top universities. We've worked with more than 15,000 students and taught over 100,000 hours of 1:1 mentorship, and we're backed by Anthos Capital and Audacious Ventures. We’ve been featured on CNN, CNBC, The TODAY Show and Forbes.
About The FlightPlan
Most college prep optimizes for the wrong thing. Students stack achievements, chase the highest GPA, and pile on activities — and arrive at college (or don't) having never asked what they actually care about. Nearly 3 in 5 young adults say they lack meaning or purpose. We think that's the real problem — and, not coincidentally, it's also what admissions officers are looking for.
The FlightPlan is an AI-powered college guidance product that helps students find their North Star as early as 8th or 9th grade, then supports them throughout high school to fulfill their potential, achieve their goals, and find their path. Built on six years of real student outcomes and trusted admissions data, it's proactive rather than reactive — it asks the right questions, helps students take action, and tracks their progress so families don't have to nag.
We launched May 1st to a sold-out Founding 100 cohort. Long term, we're building the purpose engine for a generation — the place students go not just to get into college, but to figure out who they want to become and what impact they want to have in an AI future.
About the Role
We're hiring our first Family Success Lead for The FlightPlan: the human face of the product for the families who use it.
This is a make-or-break role. You'll be the person parents and students talk to, trust, and rave about. You'll answer their questions, onboard them so they feel the magic, and serve as their monthly human touchpoint to help them get the most out of the product. You'll also be the bridge between our families and the rest of the company — carrying what you learn back to Product, and partnering with Growth to turn a great experience into a thriving community.
What makes this role unique:
- You own the relationship. Every FlightPlan family is yours to delight.
- You shape the product. You'll hear every point of confusion and every "wow" moment first, and your synthesized insights will directly steer what Product builds next.
- You build the community. Monthly office hours, fast answers, and the connective tissue that turns a tool into a movement — you'll create it alongside our Growth team.
- Mission that matters. Our families deeply value education. Beyond tactical support, you'll guide them through one of the most formative journeys of their lives: helping their student find their path to college. The impact is tangible and immediate.
What You’ll Do
In your first 90 days:
- Become the go-to person for founding families — own inbound questions across email, chat, and calls with fast, warm, genuinely helpful responses.
- Own onboarding end-to-end: get every new family from sign-up to their first real "aha" moment.
- Run our monthly FlightPlan Office Hours for future cohorts — a live forum where families get answers and feel the team behind the product.
- Build the first version of our help resources (FAQs, onboarding guides, templates) so families can self-serve the basics.
In your first year:
- Make our families so happy they refer their friends — with engagement, satisfaction, and word-of-mouth as your north-star metrics.
- Establish a tight feedback loop with Product: synthesize patterns from family conversations into clear, prioritized insights and feature requests.
- Partner with Growth to build community — events, ambassador and referral programs, and the rituals that make families feel part of something.
- Build the playbooks, systems, and (eventually) the small team that lets customer experience scale with the business.
- Keep the closest pulse on the family experience, helping shape the direction of a brand-new product as you make that experience magical, meaningful, and genuinely impactful.
Who You Are
- A magnetic connector. You light up talking to people. Parents and students trust you fast, and you genuinely love being the person they turn to.
- A natural advisor. You care about helping people find their path — not just the tactical "how do I use this" but the real guidance, drawn from your own stories and instincts about college and life.
- A jack-of-all-trades operator. You bring structure to chaos, thrive in ambiguity, and figure out whatever needs figuring out.
- A product mind. You want a seat at the table — surfacing patterns from family conversations, sharing insights, and thinking about where the roadmap goes next.
- A growth partner. Insatiably curious with a total-owner mindset. You'll work hand-in-hand with Growth to turn happy families into a movement.
- AI-first and tech-savvy. You're fluent in modern tools, comfortable standing up a CRM and the systems that keep things running, and you reach for AI by default.
- An exceptional communicator. Your writing is sharp enough that we'd trust you to talk to anyone.
- A hustler who cares deeply. You work hard because the mission matters to you, not because someone's watching.
Experience: 1–4 years of work experience, ideally in a family-facing role, startup operations, or both. What matters most is drive, judgment, and genuine care for the people you serve.
