Senior Wealth Strategy Advisor

Monstro•New York, NY

2d•$250,000 - $295,000•Hybrid

About The Position

The Senior Wealth Strategy Advisor is a foundational hire. This person is responsible for ensuring that Monstro’s financial logic is institution-grade from the outset — correct, complete, and coherent across the full scope of comprehensive wealth management. Financial planning advice built on imprecise logic compounds its errors over time. Tax assumptions that ignore estate implications, investment recommendations blind to income-phase distinctions, estate structures that conflict with insurance positioning — these are not edge cases. They are the daily reality of comprehensive wealth management, and they are precisely what AI systems get wrong first. This role exists to prevent that. You will serve as the internal authority on how Monstro’s platform reasons about wealth — not as a reviewer after the fact, but as the architect of the foundational logic itself. You will work directly with Monstro’s Founder, who brings deep wealth management and family office experience. This role expands that expertise into durable, scalable guidance that safely governs product behavior over time. You will be the internal authority across five pillars of comprehensive wealth strategy. Cash flow sits at the foundation — it governs what is possible across every other domain. Deep expertise in at least one pillar is required; the ability to reason across all five collectively is essential. Cash flow — Income, expenses, surplus allocation, debt management, liquidity planning — the foundation that determines capacity across every other domain Tax planning — Income tax strategy, Roth optimization, tax-efficient withdrawal sequencing, entity structuring, UHNW tax planning Estate planning and legal structures — Trust design, estate tax planning, GRATs, dynasty trusts, business succession, generation-skipping strategies, asset protection Financial planning — Cash flow planning, risk management, insurance integration, retirement income architecture, holistic plan construction Investments — Asset allocation, portfolio construction, asset location, withdrawal strategy, annuity design, retirement income products

Requirements

JD / Attorney, ideally with tax or estate specialization
CPA or CPA/PFS
CFP® combined with an advanced designation (JD, LL.M., AEP®, CPA)
LL.M. in Taxation
AEP® (Accredited Estate Planner), particularly at the Distinguished level
Senior-level experience equivalent to a Wealth Strategist, Advanced Planning Strategist, or senior practitioner at a top financial institution, law firm, accounting firm, or academic institution
Deep tax expertise with strong understanding of downstream implications across estate, investment, and planning domains
Demonstrated experience in estate planning and legal structures — trust design, estate tax strategy, business succession
Broad financial planning background beyond a single specialty — able to reason across the integrated wealth management system
Strong academic and technical foundation; comfort with precision and documented reasoning

Nice To Haves

Published research, authored curricula, or editorial board participation in financial planning or estate planning journals (Journal of Financial Planning, Financial Planning Review, ACTEC Law Journal, NAEPC Journal)
Experience with UHNW or family office complexity — environments where cross-domain planning errors have material consequence
Prior exposure to AI-enabled financial tools, rules-based platforms, or fintech product development
Comfort operating as a senior individual contributor without a team of analysts
Familiarity with the academic literature in comprehensive financial planning, retirement income, estate planning, and behavioral finance

Responsibilities

Define the financial framework foundation
Establish the wealth strategy and provide expertise to the product and engineering team regarding frameworks, principles, and decision guidance that govern how Monstro’s platform reasons about complex financial scenarios. Your expertise defines the foundation — what the platform understands, how it weighs tradeoffs, and where it draws boundaries.
Articulate wealth strategy in a form teams can act on
Translate your financial expertise into clear principles and structured guidance that product teams can work with you to develop into actionable requirements. The goal is articulation — making expert judgment legible and usable for the people responsible for building from it.
Model cross-domain dependencies
Document and clarify the interactions that most AI systems get wrong: how Roth conversion decisions affect estate tax exposure, how trust structures interact with income tax elections, how insurance product positioning changes with retirement income phase. Surface second- and third-order effects before they compound into downstream errors.
Distinguish rules from judgment
Identify where structured, rules-based guidance is appropriate and where expert review or human judgment is required.
Serve as subject matter expert reviewer
Act as the senior subject matter expert reviewer for early advice frameworks, edge cases, and high-stakes planning scenarios. Establish standards for accuracy, completeness, and consistency that withstand institutional scrutiny.
Act as expert, challenger, and gatekeeper
The most common failure mode in AI-assisted financial guidance is not hallucination — it is plausible-sounding advice that ignores the dependency structure of wealth strategy. You serve as the expert, challenger, and gatekeeper: ensuring that oversimplified or technically incorrect guidance never reaches the platform.