About the Role

Paraplanners and associate planners bring some of the deepest technical thinking in wealth management - the rigorous cross-domain modelling, the comprehensive plans that hold together under scrutiny, the insight that turns complexity into clarity. At Monstro, that expertise takes centre stage. We're building the financial intelligence layer that will power the next generation of AI-assisted wealth management, and we want the people who think this way at the front of it - shaping the logic, setting the standard, and building something the industry hasn't seen before.

What Monstro Is Building

Monstro is developing an AI-powered wealth management platform that must reason about complex financial scenarios with institution-grade precision. The challenge isn't getting AI to talk about financial planning - it's getting it to reason about wealth correctly, across the full dependency structure of comprehensive wealth strategy.

Tax assumptions that ignore estate implications. Investment recommendations blind to income-phase distinctions. Insurance structures that conflict with trust positioning. These aren't edge cases - they're the daily reality of comprehensive planning, and precisely where AI systems fail first.

We're hiring a Senior Wealth Planning Specialist to define how Monstro's platform reasons about wealth. Not as a reviewer after the fact, but as the architect of the foundational logic itself.

Who We're Looking For

This role is purpose-built for the professional who has been doing the real planning work - behind the scenes, with rigour - and is ready to have that expertise recognised and operationalised at scale.

You might currently be or have been:

• A Paraplanner or Senior Paraplanner at an RIA, MFO, or fee-only planning firm
• A Financial Planning Associate, Specialist, or Analyst
• A Wealth Planning Analyst within an advisor team at a bank, wirehouse, or independent RIA
• An Associate Financial Planner preparing comprehensive plans for a lead advisor
• A Planning Consultant or Advanced Planning Specialist at a software or wealthtech firm
• A non-client-facing CFP® who has chosen depth over a book of business

The environments that produce the right kind of thinker for this role:

• Multi-family offices with deep planning benches (MFO, family wealth, UHNW)
• Fee-only, comprehensive, planning-led RIAs
• Holistic practices that integrate tax, trust, and estate alongside investments
• Advanced planning teams at major institutions or law/accounting firms
• Planning software and wealthtech firms (eMoney, RightCapital, MoneyGuide, Orion, Envestnet)
• Virtual paraplanning firms where plan quality is the entire product

What You'll Do
Set the Standard for Expert Wealth Guidance

Use your financial planning expertise to shape how Monstro evaluates complex wealth guidance. You will assess AI-generated planning frameworks, decision constructs, and guidance pathways against the standards of real professional judgment - testing whether the logic is complete, the tradeoffs are properly weighed, the risks are surfaced, and the conclusions are appropriate for the client scenario. When the reasoning is incomplete or misdirected, you will provide the expert correction that teaches the system what good planning actually requires.
Serve as the Human Authority Behind Governed Financial Intelligence

Monstro's intelligence is only as strong as the professional standards used to train and approve it. In this role, you will review, refine, and approve final guidance training across wealth planning scenarios, ensuring the output reflects disciplined financial reasoning rather than generic AI responses. You will identify where AI evaluators miss nuance, where assumptions need to be challenged, and where human judgment must override automated conclusions - helping create the trusted financial logic layer behind Monstro's governed AI platform.
Distinguish Rules from Judgment

Identify where the platform can operate on structured, rules-based guidance - and where a scenario requires flagging for expert human review. This boundary-setting is itself a high-skill task, and its central to what you'll own.
Serve as the Senior Technical Reviewer

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.

The Six Planning Domains

You'll serve as internal authority across the integrated wealth management system. Deep expertise in at least one domain is required; the ability to reason across all six as a system is essential.

Cash Flow, Debt & LiquidityEvaluate guidance related to income, expenses, savings capacity, debt obligations, emergency reserves, and liquidity needs. Ensure the logic properly identifies financial constraints, prioritizes competing uses of cash, and recognizes when liquidity or debt management should take precedence over other planning strategies.

Tax PlanningReview guidance related to tax-efficient savings, withdrawal sequencing, Roth conversions, capital gains, charitable planning, asset location, and entity considerations. Ensure the logic surfaces relevant tax tradeoffs, avoids overclaiming precision, and identifies when CPA or legal review is required.

Estate, Trust & Legacy PlanningEvaluate guidance involving wills, trusts, beneficiary designations, gifting, estate tax exposure, charitable intent, business succession, and intergenerational wealth transfer. Ensure the logic captures key family, legal, and planning dependencies while escalating matters that require attorney review.

Risk Management & InsuranceReview guidance related to life, disability, long-term care, property and casualty, liability, umbrella coverage, and broader risk exposure. Ensure the logic identifies protection gaps, weighs coverage against cost and liquidity, and avoids simplistic product-driven recommendations.

Investment PlanningEvaluate guidance related to asset allocation, diversification, risk tolerance, risk capacity, time horizon, asset location, concentrated positions, and portfolio alignment with client goals. Ensure the logic properly weighs growth, preservation, income, tax efficiency, liquidity, and behavioral considerations.

Retirement Income & Distribution StrategyReview guidance related to retirement readiness, withdrawal sequencing, Social Security timing, pension decisions, annuities, required minimum distributions, longevity risk, healthcare costs, and tax-efficient distributions. Ensure the logic balances sustainability, flexibility, tax impact, and uncertainty when turning accumulated assets into retirement income.

Credentials & Experience

Credentials (one or more strongly preferred):

• 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

Experience:

• 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 - you can document complex financial logic clearly and precisely
• Comfort operating as a senior individual contributor without a team beneath you

Individual That Excel Here

The ideal candidate has spent their career doing the real technical planning work - building comprehensive plans, modelling cross-domain scenarios, catching errors before they reached the advisor, and translating expert judgment into structured analysis. Whether you come from a fee-only RIA, an MFO planning bench, a planning software or wealthtech environment, or years as the associate behind a lead advisor, what matters is this: you've never needed a book of business to do rigorous, consequential financial planning work - and you're ready for a role where that depth is the product, not the support.

What Success Looks Like

• Monstro's core financial logic reflects the standard of rigour you'd expect from a best-in-class comprehensive planning firm
• Cross-domain interactions - tax ↔ estate ↔ investment ↔ planning ↔ cash flow - are correctly modelled and defensible at every dependency point
• Product and engineering teams have clear, actionable guidance - not ambiguity that forces them into domain decisions they're not equipped to make
• Every simplification is intentional and documented - tradeoffs are explicit, not artifacts of incomplete modelling
• The financial logic you establish doesn't require structural correction as Monstro scales

Why This Role

This isn't a support role with a new title. It's a recognition that rigorous financial planning judgment is often developed behind the scenes - by the people who understand the details, dependencies, tradeoffs, and risks that make wealth guidance credible.

At Monstro, that judgment becomes central. You'll work directly with Monstro's Founder, who brings deep wealth management and family office experience, to help establish the professional standards used to evaluate, refine, and approve AI-assisted wealth guidance. Your expertise will help determine when the guidance is sound, when assumptions need to be challenged, when nuance has been missed, and when human judgment must override automated conclusions.

If you've been doing the technical planning work that makes comprehensive wealth management function - and you're ready for that expertise to shape a governed financial intelligence platform at scale - we'd like to talk.

Base Compensation Range (New York City): $140,000 - $213,750

*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).