About RoseTree
RoseTree is a premium investment education program for high-earning professionals (doctors, entrepreneurs, and executives) with $100K or more in investable capital. We help our members become the sophisticated investors in 12 months instead of three decades, using our Systematic Value Investing™ framework, without quitting their career, paying a money manager to just buy S&P500, or figuring it out alone through years of YouTube rabbit holes and expensive mistakes so the wealth they’ve earned becomes the wealth they keep, grow, and pass on.
You'll lead trading education, coaching, and bootcamps, teach our methodology, and help shape the curriculum and program as we scale. This is a builder's seat, not just a delivery seat.
Responsibilities
- Learn & teach the Systematic Value Investing™ framework
- Own and deliver the weekly group coaching call cadence with structured agendas and consistent quality
- Run independent investment research (equities, sectors, narratives, macro themes) and contribute primary analysis into the program.
- Design and deliver quarterly bootcamps (educational deep-dives) tied to the curriculum and current market conditions
- Contribute to weekly market research and methodology content alongside the CEO
- Co-build the structured year-one curriculum that takes members from fundamentals to confident execution
- Coach members on options trading, position structuring, and disciplined risk management
- Maintain an active, credible presence in the member community (Discord, group calls)
- Produce video content (tutorials, methodology explainers, market commentary) for the curriculum
- Partner with the COO & CSM on coaching quality, cadence, and member feedback loops
- Document SOPs and training materials
Requirements
We evaluate every candidate against the seven criteria below. The right person scores high on all of them.
- Ability to teach. You can take a complex concept and make it click for a beginner. You genuinely enjoy developing people, not just performing. Track record of teaching, training, or mentoring, formal or informal.
- Options expertise. Deep working knowledge of options trading and position structuring. You can teach options cleanly to someone who doesn't yet trade them, and you trade them yourself with discipline.
- Authority with HNW. Demonstrated ability to hold frame with high-net-worth professionals — handle pushback, frustration, and high-stakes questions without losing composure. You command respect in a room of successful operators.
- Research & written content. You produce clear, structured investment research.
- Video content. Comfortable on camera and able to produce clear video content. Existing channel is a plus.
- Education & curriculum building. Builder's mindset, you want to help design modules, quizzes, and milestones, not just deliver pre-built content. Experience structuring a curriculum or course is a plus.
- Grown personal portfolio. Documented track record of growing your own portfolio with real capital.
Results
Day 30
- Understand, apply and teach Systematic Value Investing™
- Program outline complete and co-owned with leadership
- Educational content produced as part of program curriculum
- Weekly group coaching call cadence live with structured agenda
- Personal trading book active and visible to members through coaching examples
- Independent research output flowing into the program from week one
- Active credible presence established in the community
Day 60
- Annual program content fully produced
- Bootcamp content reviewed and refreshed; first quarterly bootcamp delivered
- Group coaching call cadence finalized and running at consistent quality
- Member progress tracking dashboard live with coaching inputs feeding it
- Tutorial videos produced for frequently asked member questions and methodology topics
- Independent research cadence running weekly alongside the CEO
- NPS on coaching calls trending toward 70+
Day 90
- Coaching measurably contributing to 75%+ renewal rate on eligible contracts
- Quarterly bootcamp cadence sustained with refreshed content
- Year-one curriculum mature, tested, and refined based on first-cohort feedback
- Guest coach program supported if seasonal teaching is deployed
- YouTube and content contributions where appropriate to support top-of-funnel
- SOPs, training materials, and methodology documentation enable adding coaches without quality loss
Terms
- Part-time OR Full-time contractor
- Monday through Friday, US Eastern Time hours
- Some flexibility may be required around major market events
- Remote
Compensation
- $4,000-$8,000/month base + performance commission tied to renewal rate
Benefits
- Access to the RoseTree Mastermind, valued at $18,000 per year. This includes our premium investing strategy, portfolio access, education, and community.
- $1,000 annual budget for professional up-skilling.*
- Annual all-expenses-paid client retreat in Mexico. We believe in connecting in person and celebrating what we've built together.*
- Fully remote work with timezone flexibility outside scheduled coaching commitments. Work from wherever you do your best thinking.
*(for full-time team)
RoseTree Core Values
Our core values are the foundation of everything we do. The right person for this role lives these values naturally.
Progress. You take pride in showing up every day with discipline, focus, and the hunger to grow. You turn consistent, small efforts into extraordinary results over time.
Integrity. You do what is right even when no one is watching. You take ownership of your actions and follow through on your word.
Honesty. You have the courage to speak the hard truths with humility and respect. You welcome honest feedback as fuel for growth.