Senior Wealth Planning Specialist — Financial Intelligence

Monstro•New York, NY

4d•$140,000 - $213,750

About The Position

Monstro is building an AI-powered wealth management platform that requires institution-grade precision in reasoning about complex financial scenarios. This role is for a professional with deep technical expertise in wealth management, specifically in areas like cross-domain modeling and comprehensive financial planning. The Senior Wealth Planning Specialist will be instrumental in defining how the platform reasons about wealth, acting as an architect of the foundational logic rather than just a reviewer. The goal is to make financial advice more personal and accessible without compromising trust, ensuring the AI can be audited, explained, and reversed. This position offers the opportunity to operationalize expert planning knowledge at scale and shape a category-defining product in AI-assisted wealth management.

Requirements

4–7+ years constructing or reviewing comprehensive financial plans in a technical (non-client-facing or limited client-facing) capacity.
Demonstrated comfort working across tax, estate, investment, and planning domains simultaneously within a single plan.
Experience with planning software at a meaningful depth (eMoney, RightCapital, MoneyGuide, or equivalent).
Strong written communication skills; ability to document complex financial logic clearly and precisely.
Comfort operating as a senior individual contributor without a team beneath you.

Nice To Haves

CFP® — particularly combined with CPA, JD, LL.M., AEP®, or advanced designation
CPA or CPA/PFS
JD or LL.M. in Taxation, ideally with tax or estate focus
AEP® (Accredited Estate Planner)
EA with deep planning experience alongside CFP® or CPA

Responsibilities

Assess AI-generated planning frameworks, decision constructs, and guidance pathways against professional judgment standards.
Test the completeness of AI logic, the weighing of tradeoffs, the surfacing of risks, and the appropriateness of conclusions for client scenarios.
Provide expert corrections to teach the system what good planning requires when reasoning is incomplete or misdirected.
Review, refine, and approve final guidance training across wealth planning scenarios to ensure disciplined financial reasoning.
Identify nuances missed by AI evaluators, challenge assumptions, and determine when human judgment must override automated conclusions.
Identify where the platform can operate on structured, rules-based guidance and where scenarios require flagging for expert human review.
Act as the subject matter expert for early advice frameworks, edge cases, and high-stakes planning scenarios.
Establish standards for accuracy, completeness, and cross-domain consistency that would hold up to institutional scrutiny.
Evaluate guidance related to cash flow, debt, liquidity, tax planning, estate planning, risk management, insurance, investment planning, retirement income, and distribution strategy.
Ensure AI logic properly identifies financial constraints, prioritizes competing uses of cash, and recognizes when certain strategies should take precedence.
Review guidance related to tax-efficient savings, withdrawal sequencing, Roth conversions, capital gains, charitable planning, asset location, and entity considerations.
Evaluate guidance involving wills, trusts, beneficiary designations, gifting, estate tax exposure, charitable intent, business succession, and intergenerational wealth transfer.
Review guidance related to life, disability, long-term care, property and casualty, liability, umbrella coverage, and broader risk exposure.
Evaluate guidance related to asset allocation, diversification, risk tolerance, risk capacity, time horizon, asset location, concentrated positions, and portfolio alignment with client goals.
Review guidance related to retirement readiness, withdrawal sequencing, Social Security timing, pension decisions, annuities, required minimum distributions, longevity risk, healthcare costs, and tax-efficient distributions.