Location: Milan or Remote (EU time zones)
Engagement: Fractional (part time) consulting for the first months, with path to full-time post-financing
Start: ASAP
About Waypoint
Waypoint is building the AI platform for wealth managers, planners, and financial consultants serving HNWIs and their families. By automating research, modeling, and reporting, we replace fragmented workflows with a conversational AI co-pilot that enables clarity, compliance, and scale. We’re now assembling a founding team to build the future of AI-native wealth advisory. The venture has some initial pre-seed funding from Founders Factory, and an experienced, passionate cofounding team (CEO and CTO), as well as the full time build team from Founders Factory.
Why this role exists
Waypoint’s mission is to empower wealth managers, financial consultants & private bankers to give personalized, timely and holistic financial, succession planning & tax advice to customers - at scale. As a founding wealth planner, you’ll translate real-world planning cases (succession structures, holding/trust/foundation setups, donations, family agreements, insurance wrappers, liquidity events, residence/tax domicile issues, etc.) into scenarios our AI will use to generate insights, recommendations, and client-ready narratives. Your expertise will shape our data models, product features, and go-to-market with banks, private banks, and financial consultants.
What you’ll do (first 6–12 months)
Design the scenario engine

Define and prioritize a library of high-impact tax & succession planning scenarios (e.g., holding/fiduciary/trust/foundation structures; intergenerational transfers; donations; family agreements and governance; donations/advances; residence changes; insurance wrappers; liquidity events; administered vs. managed account implications for tax).
Map advisory workflows into structured inputs/outputs, data schemas, and decision trees that an AI system can reason over.
Note: Operational portfolio management is not core—the focus is on tax/structural dimensions and translating them into scenarios.

Validate with the market

Co-lead discovery interviews and feedback rounds with wealth managers/planners/consultants, run pilots, gather feedback, and iterate quickly.
Benchmark AI outputs against human best practices; define accuracy and quality thresholds.

Be our founding subject‑matter partner

Partner with Product/CTO on data sources, calculation logic, and evaluation metrics.
Advise on compliance, edge cases, and jurisdictional nuances; identify where human‑in‑the‑loop is mandatory.
Contribute to training, testing, and refinement of the AI (prompting, evaluation rubrics, red‑team­ing, QA) to minimize hallucinations and ensure trustworthy advice.

What success looks like

Scenario library shipped: 30–50 tax & succession planning scenarios with structured inputs/outputs and acceptance tests.
Advisor‑quality output­s: AI produces client‑ready summaries, comparisons, and next‑best actions that senior advisors rate ≥ 8/10 for usefulness and clarity.

What you bring

5+ years in wealth planning/wealth management, private banking, or tax/succession advisory for HNWIs; deep command of succession/estate structures and family governance.
Experience building scenarios across vehicles and assets (insurance wrappers, holding/holdcos, trusts/foundations, corporate stakes, real estate, cross‑border positions) and translating tax rules into computable logic.
Succession & governance expertise: family agreements, donations, trusts/foundations, shareholder agreements, family charters; comfort with multi‑jurisdiction cases.
Founder mindset: bias to action, comfort with ambiguity, feedback‑driven, energized by rapid iteration.
Network: relationships in the Italian & EU wealth ecosystem are a plus.
Languages: Italian and English (professional).

Engagement model (pre‑financing)

Part‑time consultant (e.g., 2–3 days/week) with clear milestones; option to convert to full‑time with meaningful equity after the next round.
Compensation: competitive day rate + advisor equity/options; conversion package discussed upfront.
Deliverables cadence: fortnightly scenario packs, monthly pilot reviews, and a running backlog groomed with Product.

How we work

Weekly build‑reviews, fast releases, evidence‑based iteration.
Strong documentation culture; “show, don’t tell” demos with real (anonymized/synthetic) data.
High ownership, low ego, and obsession with advisor and client trust.

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