Conversational UX Lead

📍 Job Overview

Job Title: Director, Conversational UX & AI Experiences – Digital Coach

Company: Fidelity Investments

Location: Boston, MA (with flexibility for Jersey City, NJ; Merrimack, NH; Smithfield, RI; Westlake, TX)

Job Type: Full-Time

Category: Conversational UX / AI Experience Design / Product Leadership

Date Posted: June 11, 2026

Experience Level: 10+ Years

Remote Status: On-site

🚀 Role Summary

• Lead the strategic definition and execution of end-to-end conversational user experiences for an AI-powered financial assistant, focusing on complex, stateful, and multi-session interactions.

• Drive innovation at the intersection of conversational design, frontend systems, and AI product development within a fast-paced, early-growth environment.

• Translate intricate financial policies, guardrails, and compliance requirements into intuitive, human-centered digital experiences that build customer trust.

• Collaborate closely with platform AI, product management, and engineering teams to shape the behavior, engagement, and overall architecture of the AI assistant.

• Own rapid prototyping efforts and continuously iterate on user experiences based on feedback, behavioral insights, and quality metrics.

📝 Enhancement Note: While the job title is "Conversational UX Lead," the responsibilities and experience requirements (8+ years, Director level) strongly suggest a senior individual contributor role with significant leadership and strategic influence, rather than direct people management. The focus on "defining how our AI-powered financial assistant behaves" and "owning the end-to-end conversational experience" points to a high-impact role crucial for the success of Fidelity Digital Coach. The "Operations Category" has been defined as Conversational UX / AI Experience Design / Product Leadership to best reflect the specialized nature of this role within the broader GTM and product development ecosystem.

📈 Primary Responsibilities

• Define and evolve the conversational architecture for an AI-powered financial assistant, including conversation states, memory strategies, re-entry points, and holistic UX patterns.

• Design and prototype multi-turn, multi-session user journeys that guide customers through complex financial scenarios, ensuring clarity and trust.

• Partner with platform AI teams to influence the development of AI models, ensuring their outputs align with desired conversational flow and user experience objectives.

• Translate financial policies, regulatory constraints, and compliance guardrails into actionable design specifications and user-facing language.

• Lead front-end experience design initiatives, focusing on interaction models that enhance engagement and build rapport with users.

• Develop and implement strategies for continuous improvement by leveraging user feedback, behavioral analytics, and quality assurance signals.

• Collaborate with cross-functional stakeholders including product managers, engineers, designers, risk, and compliance teams to ensure alignment and successful feature delivery.

• Champion a human-centered design approach to ensure the AI assistant is perceived as a trusted, reliable, and empathetic financial guide.

📝 Enhancement Note: The core responsibilities emphasize a blend of strategic design leadership and hands-on execution. The need to "translate financial policies, guardrails, and compliance constraints" highlights a critical aspect of operating within a regulated industry, requiring a deep understanding of how to balance innovation with risk mitigation. This role is less about traditional sales or revenue operations and more about the operationalization of a sophisticated AI product's user experience and its integration into existing financial services frameworks.

🎓 Skills & Qualifications

Education: While no specific degree is mandated, a Bachelor's or Master's degree in Human-Computer Interaction (HCI), UX Design, Computer Science, Cognitive Psychology, or a related field is strongly implied given the focus on user experience and AI.

Experience: 8+ years of progressive experience in User Experience (UX) design, product design, or specialized conversational design, with a significant portion focused on AI-powered or agent-based systems.

Required Skills:

• Proven expertise in designing complex, stateful, multi-turn, and multi-session conversational user journeys.

• Strong systems thinking capabilities, with a demonstrated ability to collaborate effectively across product, engineering, and AI platform teams.

• Hands-on experience in shaping front-end user experiences and interaction models for customer-facing digital products.

• Deep understanding of conversational AI principles, including natural language understanding (NLU) and natural language generation (NLG) impacts on UX.

• Ability to balance innovative design with clarity, trust, and compliance requirements in regulated environments.

• Proficiency in rapid prototyping tools and methodologies to quickly test and validate design concepts.

• Excellent communication and collaboration skills, with the ability to articulate complex design decisions to technical and non-technical stakeholders. Preferred Skills:

• Experience within the financial services, fintech, or other highly regulated domains.

• Familiarity with AI model inputs, context management, and output shaping for conversational agents.

• Experience with user research, A/B testing, and leveraging behavioral insights for iterative design improvements.

• Understanding of financial planning, investment, or banking concepts.

• Familiarity with Agile development methodologies and cross-functional team collaboration.

📝 Enhancement Note: The "10+" experience level derived from the "8+ years" requirement indicates a senior-level individual contributor. The emphasis on "systems thinking" and "collaborating across product, engineering, and AI platform teams" is key for operations professionals transitioning into product-focused roles or those looking for roles that bridge design and technical execution. The preference for finance/fintech experience highlights the domain-specific knowledge crucial for success in this role.

📊 Process & Systems Portfolio Requirements

Portfolio Essentials:

• Showcase of end-to-end conversational design projects, demonstrating a clear understanding of user needs, problem definition, and solution development.

• Examples of complex, multi-session user journeys, detailing the interaction states, memory mechanisms, and re-entry strategies employed.

• Case studies illustrating the translation of complex requirements (e.g., financial policies, compliance rules) into intuitive and user-friendly conversational flows.

• Prototypes or interactive demos that highlight front-end experience design and interaction modeling for AI-driven products.

• Documentation of how user feedback, data, and quality signals were used to iterate and improve conversational experiences. Process Documentation:

• Workflow diagrams and design documentation for stateful conversational agents.

• Evidence of collaboration with AI/ML teams to shape model inputs and outputs for optimal UX.

• Examples of how compliance and regulatory constraints were integrated into conversational design.

• Methodologies for user testing, feedback collection, and iterative refinement of AI-driven interactions.

📝 Enhancement Note: For a role like this, a portfolio is paramount. It needs to go beyond static UI designs to demonstrate an understanding of dynamic conversational flows, AI integration, and the ability to manage complex user states. Candidates should be prepared to articulate their design process, decision-making rationale, and the impact of their work, especially in regulated environments.

💵 Compensation & Benefits

Salary Range: $126,000 - $255,000 USD per year. Placement in the range will depend on factors such as job responsibilities, scope, geographic location, candidate's relevant experience, and other applicable criteria.

Benefits:

• Comprehensive health care coverage (medical, dental, vision).

• Emotional well-being support programs.

• Market-leading retirement savings plan (e.g., 401k with company match).

• Generous Paid Time Off (PTO) and parental leave policies.

• Charitable giving employee match program.

• Educational assistance, including:

  • Student loan repayment support.

  • Tuition reimbursement for further learning.

  • Access to learning resources for career development. Working Hours: 40 hours per week. While the role is on-site, flexibility may be available depending on team needs and project deadlines, though core hours will be expected for collaborative work.

📝 Enhancement Note: The salary range provided is substantial, reflecting a senior-level individual contributor role with significant strategic impact. The breadth of benefits offered by Fidelity Investments is comprehensive, covering health, financial well-being, work-life balance, and professional development, which are attractive to experienced professionals. The note about "bonus or other variable compensation" suggests potential for performance-based incentives, common for senior roles.

🎯 Team & Company Context

🏢 Company Culture

Industry: Financial Services / Fintech. Fidelity Investments is a leading provider of investment management, financial planning, and retirement services. The Digital Coach initiative operates within Fidelity Labs, an incubator for new business ventures, blending the stability of a large corporation with the agility of a startup.

Company Size: Fidelity Investments is a very large, global financial services organization, employing tens of thousands of individuals worldwide. This scale offers resources, stability, and significant market reach.

Founded: Fidelity was founded in 1946. Fidelity Labs was established in 2005, indicating a long-standing commitment to innovation within the company.

Team Structure:

• The Digital Coach team is part of Fidelity Labs, operating as an "early-growth" environment, suggesting a lean, agile, and cross-functional team structure.

• This role reports into leadership within Fidelity Labs or the Digital Coach initiative, working closely with Product Management, Engineering, and Platform AI teams.

• Collaboration is expected to be high, with frequent interaction across disciplines to bring AI-driven financial guidance to life. Methodology:

• Data-driven decision-making, leveraging user feedback, behavioral insights, and quality signals to iterate on AI-powered experiences.

• Agile and iterative development processes, common in startup-like environments, enabling rapid prototyping and continuous improvement.

• Human-centered design principles are paramount, ensuring that technology serves customer needs effectively and builds trust.

• Focus on integrating new digital experiences with Fidelity's existing, robust financial platforms and adhering to stringent regulatory standards.

Company Website: https://labs.fidelity.com/

📝 Enhancement Note: Understanding the Fidelity Labs context is crucial. It means operating with the resources and credibility of a major financial institution while adopting the speed and innovative spirit of a startup. This duality influences the pace of work, the types of problems tackled, and the required adaptability of team members.

📈 Career & Growth Analysis

Operations Career Level: This role represents a senior individual contributor path, often termed "Principal," "Lead," or "Director" level, focusing on deep domain expertise in Conversational UX and AI product development. It's a leadership position in terms of strategic influence and technical ownership, rather than direct people management.

Reporting Structure: The role likely reports to a Director or VP within Fidelity Labs or the Digital Coach initiative. It involves close collaboration with peer leads in Product Management and Engineering.

Operations Impact: The impact is direct and significant: shaping a core customer-facing AI product that aims to scale financial guidance to millions. Success means driving customer engagement, trust, and potentially improving financial outcomes for users, which indirectly supports Fidelity's broader business objectives and customer retention.

Growth Opportunities:

• Specialization: Deepen expertise in Conversational AI UX, stateful interactions, and AI product strategy within a regulated financial domain.

• Leadership: Grow into a principal or architect role, shaping the future of AI-driven customer experiences across Fidelity.

• Cross-Functional Exposure: Gain in-depth understanding of AI platform development, financial product strategy, and regulatory compliance.

• Innovation: Contribute to cutting-edge financial technology within a dedicated innovation hub (Fidelity Labs).

📝 Enhancement Note: This role offers a unique opportunity to pioneer AI-driven financial guidance, a high-growth area. The growth trajectory is likely focused on increasing strategic impact and technical leadership within the AI/UX domain, rather than traditional management paths. Candidates should highlight their ability to influence product direction and technical architecture.

🌐 Work Environment

Office Type: The role is designated as "On-site," indicating a primary work location within one of Fidelity's physical offices. This supports in-person collaboration, team building, and access to office resources.

Office Location(s): Multiple locations are listed, including Boston, MA; Jersey City, NJ; Merrimack, NH; Smithfield, RI; and Westlake, TX, suggesting flexibility in office assignment or team distribution across these hubs.

Workspace Context:

• A collaborative and innovative environment typical of Fidelity Labs, blending startup energy with corporate resources.

• Opportunities to work with cutting-edge AI technologies and contribute to a product with significant customer reach.

• Access to a professional workspace designed to foster collaboration and productivity.

• Regular interaction with a diverse team of product managers, engineers, designers, and AI specialists.

Work Schedule: Standard 40-hour work week, with the expectation of on-site presence. While core hours will be observed for team collaboration, the fast-paced nature of an incubator might require occasional flexibility to meet project milestones.

📝 Enhancement Note: The "On-site" requirement is important. While Fidelity is a large organization, this specific role is positioned within an office-based team, emphasizing the value placed on in-person collaboration for this innovative project. Candidates should consider their comfort level with this arrangement.

📄 Application & Portfolio Review Process

Interview Process:

1. Initial Screening: Recruiter or hiring manager screens resume and potentially conducts a brief introductory call to assess basic qualifications and interest.

2. Portfolio Deep Dive: A dedicated session to review your portfolio. Expect to walk through 1-2 key projects, detailing your role, design process, challenges, solutions, and outcomes, with a strong emphasis on conversational design and AI integration.

3. Technical/Design Interview: In-depth discussion on conversational design principles, stateful interactions, AI UX, and how you approach complex problem-solving. May involve whiteboard exercises or scenario-based questions.

4. Cross-functional Collaboration Interview: Discussion with peers from Product Management, Engineering, and AI teams to assess your ability to collaborate, communicate, and align with diverse stakeholders.

5. Leadership/Director Interview: Conversation with senior leadership to assess strategic thinking, vision for conversational AI in finance, and cultural fit within Fidelity Labs.

Portfolio Review Tips:

• Focus on AI & Conversation: Prioritize projects that clearly demonstrate your expertise in conversational UX, AI-driven products, and complex user journeys.

• Showcase Process: Detail your design process from problem identification through iteration and launch. Explain why you made certain decisions.

• Quantify Impact: Where possible, use metrics (e.g., engagement rates, task completion, user satisfaction) to demonstrate the success of your designs.

• Address Constraints: Highlight how you navigated regulatory, compliance, or policy constraints in your designs, especially if relevant to finance.

• Prepare for Statefulness: Be ready to explain how you design for memory, context, and multi-session interactions.

Challenge Preparation:

• Anticipate scenarios where you might need to design a conversational flow for a specific financial task (e.g., checking account balance, understanding an investment option, navigating a policy).

• Prepare to discuss how you would balance user needs with Fidelity's brand, policies, and regulatory requirements.

• Consider how you would measure the success of an AI conversational experience.

📝 Enhancement Note: The interview process is structured to rigorously assess both design craft and collaborative ability. A strong portfolio that specifically addresses AI and conversational complexities is non-negotiable. Candidates should prepare to articulate how their UX expertise translates into tangible business and customer value within a regulated domain.

🛠 Tools & Technology Stack

Primary Tools:

• Conversational Design Platforms: Tools for scripting, prototyping, and testing conversational flows (e.g., Botmock, Voiceflow, specialized internal tools).

• Prototyping Tools: For front-end and interaction design (e.g., Figma, Sketch, Adobe XD).

• User Research & Analytics: Tools for gathering user feedback and analyzing behavioral data (e.g., UserTesting.com, Amplitude, Google Analytics, internal BI tools).

• Collaboration Tools: For team communication and project management (e.g., Slack, Microsoft Teams, Jira, Confluence).

Analytics & Reporting:

• Familiarity with data analysis and reporting tools to track key UX metrics and inform design decisions.

• Ability to interpret data from AI model performance and user interaction logs. CRM & Automation:

• While not explicitly a CRM role, understanding how conversational AI integrates with customer data platforms and backend systems is beneficial.

• Familiarity with API integrations and workflow automation concepts will be helpful.

📝 Enhancement Note: Specific tool names are not provided, but the description implies a need for proficiency in industry-standard UX/design tools and a willingness to learn proprietary or specialized AI/conversational design platforms. The emphasis is on the application of these tools to solve complex problems, rather than just listing them.

👥 Team Culture & Values

Operations Values:

• Customer-Centricity: A deep commitment to understanding and serving customer needs through innovative and empathetic digital experiences.

• Innovation & Agility: Embracing a startup mindset within Fidelity Labs, encouraging experimentation, rapid iteration, and pushing the boundaries of financial services.

• Collaboration & Trust: Building strong partnerships across product, engineering, and AI teams, fostering an environment of mutual respect and shared ownership.

• Data-Driven Decisions: Utilizing insights from user data, feedback, and performance metrics to guide design choices and product strategy.

• Integrity & Compliance: Upholding the highest standards of trust, security, and regulatory adherence in all aspects of design and product development.

Collaboration Style:

• Highly collaborative, with a strong emphasis on cross-functional teamwork to achieve shared goals.

• Open communication and a willingness to provide and receive constructive feedback.

• Proactive engagement with stakeholders to ensure alignment and manage expectations.

• A culture that encourages learning from both successes and failures.

📝 Enhancement Note: The culture is a blend of a large, established financial institution's rigor and a startup's dynamism. Candidates should demonstrate an ability to thrive in this hybrid environment, valuing both innovation and the responsibility that comes with operating in the financial sector.

⚡ Challenges & Growth Opportunities

Challenges:

• Balancing Innovation with Regulation: Designing cutting-edge AI experiences while strictly adhering to financial regulations and compliance policies.

• Stateful Conversation Complexity: Mastering the design of long-term, multi-session conversations that maintain context and build rapport over time.

• AI Model Integration: Effectively collaborating with AI platform teams to shape model behavior and outputs for optimal user experience.

• Building Trust in AI: Creating an AI assistant that customers trust with sensitive financial information and guidance.

• Scaling Guidance: Developing a scalable solution that provides personalized financial guidance to millions of diverse customers.

Learning & Development Opportunities:

• Specialized AI UX Training: Deepen expertise in conversational design, AI ethics, and emerging AI technologies.

• Financial Domain Expertise: Gain a comprehensive understanding of financial planning, investment, and wealth management.

• Leadership & Strategy: Develop strategic thinking and product leadership skills within a major financial services incubator.

• Industry Conferences: Potential to attend relevant UX, AI, and fintech conferences.

📝 Enhancement Note: This role presents significant intellectual challenges, particularly in bridging advanced AI capabilities with the stringent requirements of the financial services industry. The growth opportunities are substantial for those who excel in this complex domain.

💡 Interview Preparation

Strategy Questions:

• "Describe a complex stateful conversational experience you designed. What were the key challenges, your approach, and the outcome?" (Focus on memory, re-entry, multi-session design.)

• "How would you approach designing a conversational flow for a customer seeking advice on a specific investment product, considering Fidelity's compliance requirements?" (Assess ability to balance UX with regulation.)

• "Imagine our AI assistant needs to remember a user's previous financial goal from a prior session. How would you design for this 'memory' and ensure it's used appropriately in the current conversation?" (Test understanding of conversational state management.)

• "How do you collaborate with AI/ML engineers to ensure the AI's capabilities and limitations are reflected effectively in the user experience?" (Evaluate cross-functional collaboration and AI understanding.) Company & Culture Questions:

• "What interests you about Fidelity Labs and the Digital Coach initiative specifically?" (Demonstrate research and genuine interest.)

• "How do you think an AI-powered financial assistant can build trust with customers?" (Connect to Fidelity's brand and customer-centric values.)

• "Describe a time you had to balance user needs with business/regulatory constraints. How did you navigate that?" (Assess problem-solving and stakeholder management.) Portfolio Presentation Strategy:

• Narrative Arc: Structure your portfolio presentation around storytelling – the user problem, your design process, your specific contributions, the solution, and the impact.

• Visual Clarity: Use clear visuals (screenshots, flow diagrams, prototypes) to illustrate your points.

• Focus on AI/Conversation: For each project, explicitly call out the AI or conversational design elements and your role in them.

• Quantify Impact: Be ready to discuss metrics or qualitative feedback that demonstrate the success of your work.

• Prepare for Q&A: Anticipate questions about your design decisions, trade-offs, and alternative approaches.

📝 Enhancement Note: Preparation should focus on demonstrating a deep understanding of conversational design principles, AI integration, and the ability to navigate complex, regulated environments. Candidates should be able to articulate their thought process and showcase tangible examples of their work.

📌 Application Steps

To apply for this Conversational UX Lead position:

• Submit your application through the Fidelity Careers portal link provided.

• Portfolio Customization: Tailor your portfolio to highlight projects demonstrating expertise in conversational UX, AI-driven experiences, stateful design, and working within regulated industries. Prioritize examples that show your ability to translate complex requirements into user-friendly interactions.

• Resume Optimization: Ensure your resume clearly details your experience with AI, conversational design, user journeys, and cross-functional collaboration, using keywords from the job description. Quantify achievements where possible.

• Interview Preparation: Practice articulating your design process, rationale, and the impact of your work. Prepare specific examples for behavioral questions and be ready to discuss hypothetical design challenges related to AI in finance.

• Company Research: Thoroughly research Fidelity Investments, Fidelity Labs, and the Digital Coach initiative. Understand their mission, values, and the competitive landscape of AI in financial services.

⚠️ Important Notice: This enhanced job description includes AI-generated insights and operations industry-standard assumptions. All details, particularly regarding specific responsibilities, team dynamics, and interview processes, should be verified directly with the hiring organization during the application and interview stages.