About Monstro

Monstro is the operating system for governed financial intelligence. We build the infrastructure that enables artificial intelligence to operate safely, explainably, and at institutional scale in highly regulated financial domains.

We exist because the level of financial guidance historically available to a small group should be accessible to many more people. By combining AI with deep institutional infrastructure, we help financial institutions deliver more personalized, responsible, and life-changing financial support to millions of individuals.

We’re building mission-critical systems in a regulated domain, and we care deeply about doing it right. If you’re motivated by meaningful problems, high standards, and improving financial outcomes for people who have never had access to them before, you’ll feel at home here.

About the Role

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.

Domain Scope

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

What You’ll Do

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.

What Success Looks Like

• Monstro’s core financial logic reflects institution-grade wealth strategy rigor that expert reviewers would not find fault with
• Cross-domain interactions — tax ↔ estate ↔ investment ↔ planning ↔ cash flow — are correctly modeled and defensible at every dependency point
• Product and engineering teams have clear, actionable guidance — not ambiguity that forces them to make domain decisions they are not equipped to make
• The financial logic established in this role is precise and complete enough that it does not require structural correction as Monstro grows in scope and complexity
• Every simplification is intentional and documented — tradeoffs are explicit, not artifacts of incomplete modeling

What We’re Looking For

Required credentials (one or more):

• 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

Required experience: 

• 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

The Strongest Candidates Will Reflect One of These Profiles

The practitioner-academic: e.g., CFP® with a PhD, or JD with an academic appointment. Has translated domain expertise into frameworks, curricula, or published research — the exact cognitive habit this role requires for articulating wealth strategy logic clearly and completely.

The Advanced Planning Strategist: e.g., CPA/JD/AEP® from a major institution, law firm, or accounting firm. Has reviewed complex, multi-domain wealth plans under institutional accountability. Accustomed to the standard of rigor Monstro’s platform must meet.

The cross-credentialed specialist: e.g., CPA + JD + CFP®, or JD + LL.M. + AEP®. Holds credentials spanning tax, legal, and planning domains simultaneously. Multiple credentials across domains are evidence of the integrated thinking this role requires — not resume decoration

The financial framework builder: e.g., prior experience building guidance frameworks, institutional playbooks, or structured advisory systems. Has experience translating expert financial judgment into documented frameworks, structured guidance, or institutional playbooks — whether at a major firm, fintech, or in an advisory capacity. Understands how expertise becomes process.

Additional Signals We Value

• 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

Location & Work Model

Hybrid — New York City. Preference for candidates based in or willing to work from New York City. 

Why Monstro?

• Ownership & Impact: Shape the future of AI-powered finance—building a category-defining product used by consumers and institutions around the world.
• Elite Team: Join a team with leadership that has a track record of scaling companies from early stage to major exits.
• Principles-Driven Culture: Work in a culture that values speed, ownership, and impact—what most companies achieve in 90 days, we do in 45.
• Comprehensive Compensation Package: Competitive salary, equity, and robust benefits package, including paid health, vision, dental, and disability coverage.

Compensation & Benefits

• Base Salary: $237,000 – $280,000 (New York City range)
• Equity participation
• Comprehensive benefits: paid health, vision, dental, and disability coverage

*The posted range reflects the base salary for this role across the market ranges for each location. Final compensation will depend on a variety of factors, including experience, skills, internal leveling, and market conditions, and will be offered within the stated range in accordance with applicable pay transparency laws.

A Note on Interviewing: We sometimes use AI note-takers to help us transcribe interview notes, so we can be more present in your interview. If you’d like to opt out of us using automatic transcribers, please note this in the free text field in your application, otherwise we’ll take your application as confirmation that you’re happy for us to use notetakers (whether added to video calls or in the background).