Fractional Tax

Location:Milan or Remote (EU time zones)Engagement:Fractional (part time) consulting for the first months, with path to full-time post-financingStart:ASAPAbout WaypointWaypoint 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 co-founding team (CEO and CTO), as well as the full time build team from Founders Factory.Why this role existsWaypoint's mission is to empower wealth managers, financial consultants & private bankers to givepersonalized, timelyandholisticfinancial, 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 engineDefine 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 intostructured inputs/outputs, data schemas, and decision trees that an AI system can reason over.Note:Operational portfolio management is not core — the focus is ontax/structuraldimensions and translating them into scenarios.Validate with the marketCo-lead discovery interviews and feedback rounds with wealth managers/planners/consultants, run pilots, gather feedback, and iterate quickly.BenchmarkAI outputs against human best practices; define accuracy and quality thresholds.Be our founding subject-matter partnerPartner with Product/CTO ondata sources, calculation logic, and evaluation metrics.Advise oncompliance, edge cases, and jurisdictional nuances; identify where human-in-the-loop is mandatory.Contribute totraining, testing, and refinementof the AI (prompting, evaluation rubrics, red-teaming, QA) to minimize hallucinations and ensure trustworthy advice.What success looks likeScenario library shipped:***** 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= 8/10for usefulness and clarity.What you bring5+ yearsin wealth planning/wealth management, private banking, ortax/succession advisoryfor HNWIs; deep command of succession/estate structures and family governance.Experiencebuilding scenariosacross vehicles and assets (insurance wrappers, holding/holdcos, trusts/foundations, corporate stakes, real estate, cross-border positions) andtranslating tax rulesinto 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 withmeaningful equityafter 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 workWeekly 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.#J-*****-Ljbffr