Want to know if this job is worth applying to?
Boston, Massachusetts, United States
Onsite
Director, Conversational UX & AI Experiences – Join Fidelity Digital Coach, a Fidelity Labs company
Digital Coach is scaling holistic financial guidance to millions of Fidelity customers who today have limited access to personalized, end‑to‑end financial support. As Director of Conversational UX & AI Experiences on the Digital Coach team, you will define how our AI‑powered financial assistant behaves, engages, and builds trust with customers across ongoing, multi‑session interactions.
This is a hands‑on leadership role for a senior individual contributor who thrives at the intersection of conversational design, frontend systems, and AI‑powered products. You will work closely with product, engineering, and platform AI teams in a fast‑moving, early‑growth environment, shaping differentiated, human‑centered experiences while integrating with Fidelity’s broader platforms, policies, and services.
THE ROLE
AS DIRECTOR OF CONVERSATIONAL UX & AI EXPERIENCES ON DIGITAL COACH, YOU WILL:
Own the end‑to‑end conversational experience for an AI‑powered financial chatbot, from concept through production
Design and evolve agent‑based, stateful conversational experiences beyond traditional chat interfaces
Define conversation states, memory strategies, re‑entry moments, and UX patterns for financial guidance
Partner closely with platform AI teams to shape inputs, context, and outputs into trusted, human‑centered experiences
Lead front‑end experience design, conversational UX, and rapid prototyping efforts
Translate financial policies, guardrails, and compliance constraints into clear, intuitive user experiences
Collaborate with product, engineering, design, and risk partners to ensure alignment across teams
Continuously iterate on experiences using user feedback, behavioral insights, and quality signals
THE EXPERTISE AND SKILLS YOU BRING
8+ years of experience in UX, product, or conversational design, including AI‑powered or agent‑based systems
Proven ability to design complex, stateful, multi‑turn and multi‑session user journeys
Strong systems thinking, with fluency collaborating across product, engineering, and AI platform teams
Hands‑on experience shaping front‑end experiences and interaction models for customer‑facing products
Ability to balance innovation with clarity, trust, and compliance in regulated environments
Experience in finance, fintech, or other regulated domains strongly preferred
THE TEAM
This role is part of Fidelity Labs, Fidelity Investments’ in‑house new business incubator. Founded in 2005, Fidelity Labs has played a key role in incubating and scaling innovative businesses that shape the future of financial services.
Digital Coach is a Labs‑incubated initiative focused on expanding access to holistic financial guidance through AI‑powered, human‑centered digital experiences. Fidelity Labs offers the creativity and speed of a startup environment paired with the scale, trust, and stability of an industry leader.
Learn more at: https://labs.fidelity.com
Fidelity’s Onsite Working Model
Fidelity is transitioning to a full-time onsite working model through a phased rollout across regions and roles. Currently, some roles and locations require 100% onsite presence, while others require less. Onsite expectations are likely to evolve as the rollout continues. This transition does not apply to fully remote roles.
Placement in the range will vary based on job responsibilities and scope, geographic location, candidate’s relevant experience, and other factors.
Base salary is only part of the total compensation package. Depending on the position and eligibility requirements, the offer package may also include bonus or other variable compensation.
We offer a wide range of benefits to meet your evolving needs and help you live your best life at work and at home. These benefits include comprehensive health care coverage and emotional well-being support, market-leading retirement, generous paid time off and parental leave, charitable giving employee match program, and educational assistance including student loan repayment, tuition reimbursement, and learning resources to develop your career. Note, the application window closes when the position is filled or unposted.
Please be advised that Fidelity’s business is governed by the provisions of the Securities Exchange Act of 1934, the Investment Advisers Act of 1940, the Investment Company Act of 1940, ERISA, numerous state laws governing securities, investment and retirement-related financial activities and the rules and regulations of numerous self-regulatory organizations, including FINRA, among others. Those laws and regulations may restrict Fidelity from hiring and/or associating with individuals with certain Criminal Histories.