UX Designer – Conversational AI / Microsoft Copilot

📍 Job Overview

Job Title: UX Designer – Conversational AI / Microsoft Copilot

Company: Ontrac Solutions

Location: Chicago, Illinois, United States

Job Type: CONTRACTOR

Category: User Experience (UX) Design / Conversational AI

Date Posted: May 21, 2026

Experience Level: Mid-Level (2-5 years)

Remote Status: Fully Remote (US-based)

🚀 Role Summary

• Design and develop user-centered conversational AI experiences, focusing on voice and chat-based virtual assistants, including Microsoft Copilot integrations.

• Translate complex user needs, business objectives, and technical constraints into intuitive and scalable conversational flows, journey maps, and interaction specifications.

• Utilize Figma for wireframing, prototyping, and creating detailed design artifacts to ensure stakeholder alignment throughout the Software Development Life Cycle (SDLC).

• Facilitate design workshops and alignment sessions, demonstrating strong communication and leadership skills to bridge the gap between technical and non-technical teams.

📝 Enhancement Note: While the role title is "UX Designer," the specific emphasis on "Conversational AI" and "Microsoft Copilot" positions this as a specialized UX role within the broader AI and Product Development landscape. The contractor employment type and remote flexibility suggest a project-based engagement requiring a high degree of autonomy and self-management. The provided hourly rate aligns with mid-level UX designers in major tech hubs, especially those with niche AI expertise.

📈 Primary Responsibilities

• Collaborate with product managers, engineers, and cross-functional stakeholders to deeply understand user needs, business objectives, and technical feasibility for conversational AI initiatives.

• Design comprehensive conversational experiences across various channels, including voice (IVR, virtual assistants), chat, and Microsoft Copilot-integrated platforms.

• Develop detailed UX artifacts such as journey maps, user flows, wireframes, interactive prototypes, sample dialogs, and precise interaction specifications.

• Employ Figma to create visually compelling and functional design assets that facilitate clear communication and decision-making among diverse teams.

• Lead and facilitate design thinking workshops, proposal discussions, and critical alignment sessions with both internal teams and external business stakeholders.

• Architect and build thoughtful, user-centric conversational flows tailored to specific use cases, including customer-facing, patient-facing, and professional-facing applications.

• Conduct thorough usability evaluations of existing and proposed conversational experiences to ensure consistency, effectiveness, and optimal performance across the entire customer journey.

• Support the iterative tuning of conversational AI models by analyzing qualitative feedback and quantitative performance data to drive continuous improvement.

• Create clear recording scripts for voice interactions and maintain organized prompt catalogs, ensuring strict adherence to established persona guidelines and brand voice.

• Actively participate in user acceptance testing (UAT) and functional testing phases to validate that applications meet design specifications and user expectations.

• Apply human-centered design methodologies to effectively frame complex problems, identify recurring patterns, uncover innovative opportunities, and visualize potential user-centric solutions.

• Maintain up-to-date knowledge of advancements in conversational AI, voice interaction design, Microsoft Copilot functionalities, and emerging UX best practices to inform design decisions.

• Provide mentorship and guidance to less experienced designers, fostering a collaborative and knowledge-sharing environment within the design team.

📝 Enhancement Note: The responsibilities highlight a blend of core UX design tasks with specialized conversational AI design elements. Emphasis is placed on collaboration, artifact creation (flows, wireframes, prototypes), workshop facilitation, and performance analysis. The mention of "customer, patient, and professional-facing use cases" suggests potential application in healthcare, enterprise services, or customer support sectors. The need to "support conversation tuning" implies a data-driven approach and engagement with AI model performance.

🎓 Skills & Qualifications

Education:

• Bachelor’s degree in Human-Computer Interaction, Linguistics, Cognitive Science, Graphic Design, Digital Communications, Computer Science, Engineering, or a closely related field is preferred. Experience:

• 3–5 years of progressive experience in UX design, interaction design, conversational design, or a related field, with a strong portfolio demonstrating successful project outcomes.

• Proven experience in designing complex conversational experiences, including voice interfaces (IVR, virtual assistants), chat applications, and AI-powered chatbots.

• Hands-on, practical experience designing with or for Microsoft Copilot or other significant Microsoft AI and productivity tools is a strong requirement.

• Demonstrated proficiency in creating detailed wireframes, user flows, and interactive prototypes using Figma.

• Solid understanding of the Software Development Life Cycle (SDLC) and practical experience collaborating effectively with product management and engineering teams.

• Experience in developing comprehensive user flows, detailed wireframes, interactive prototypes, sample dialogs, and clear interface specifications.

• Proven ability to facilitate effective design workshops, lead proposal discussions, and drive stakeholder alignment sessions.

• Excellent verbal and written communication skills, strong organizational abilities, and demonstrated leadership potential.

• Ability to work autonomously and effectively manage tasks and priorities in a fully remote work environment. Required Skills:

• Conversational AI Design Principles

• Microsoft Copilot Design & Integration

• Figma (Wireframing, Prototyping)

• User Flow Mapping & Diagramming

• Interaction Design Specifications

• IVR Application Design

• Voice User Interface (VUI) Design

• Human-Centered Design Methodologies

• Stakeholder Management & Alignment

• Workshop Facilitation

• Software Development Life Cycle (SDLC) Understanding Preferred Skills:

• Experience with IVR platform design tools and methodologies.

• Familiarity with speech recognition software, advanced voice interfaces, or multimodal speech interaction design.

• Knowledge of core speech and language technologies, including:

  • Automatic Speech Recognition (ASR)
  • Natural Language Understanding (NLU)
  • Voice User Interfaces (VUI)
  • Advanced Chat-based Conversational Design patterns

• Deep understanding of established VUI design patterns and best practices.

• Experience in developing and designing voice personas based on user research, demographic data, and brand guidelines.

• Experience supporting the design and implementation of enterprise-scale conversational AI or customer experience platforms.

📝 Enhancement Note: The experience requirement is clearly defined as 3-5 years, placing this role at a mid-level. The emphasis on Microsoft Copilot and Figma are critical technical requirements. Preferred qualifications delve deeper into the nuances of conversational AI technology and advanced VUI design, indicating that candidates with this specialized knowledge will be highly competitive. The educational requirements are flexible, prioritizing practical experience and relevant degrees.

📊 Process & Systems Portfolio Requirements

Portfolio Essentials:

• Showcase at least 2-3 distinct projects demonstrating expertise in conversational AI design (voice, chat, or virtual assistants).

• Include examples of user journey maps, detailed user flows, and wireframes specifically for conversational interfaces.

• Present interactive prototypes created in Figma that illustrate key conversational interactions and user flows.

• Provide sample dialogs or conversation scripts that highlight persona development and effective user-task completion.

• Quantify design impact where possible, detailing improvements in user satisfaction, task completion rates, or efficiency gains resulting from your designs. Process Documentation:

• Demonstrate a clear understanding of how conversational design integrates into the broader SDLC, from ideation to testing and iteration.

• Show examples of how you have translated user research and stakeholder requirements into actionable design specifications for development teams.

• Illustrate your approach to evaluating and iterating on conversational designs based on user feedback, usability testing, and performance metrics.

📝 Enhancement Note: For a UX role, especially in conversational AI, a strong, project-based portfolio is paramount. The emphasis here is on showcasing specific deliverables related to conversational design and demonstrating the ability to integrate these designs into a development lifecycle. Quantifying impact is crucial for demonstrating value.

💵 Compensation & Benefits

Salary Range:

• $70 - $80 per hour (USD)

• This translates to approximately $145,600 - $166,400 annually for a full-time, 40-hour work week. Benefits:

• As a contractor role, standard employee benefits like health insurance, paid time off, and retirement plans are typically not included.

• Potential benefits may include:

  • Flexible work schedule and remote work arrangement, offering significant autonomy.

  • Opportunity to work on high-profile, cutting-edge AI projects with a leading organization.

  • Potential for contract extension or future project opportunities with Ontrac Solutions.

  • Exposure to advanced conversational AI technologies and platforms. Working Hours:

• Standard full-time hours are expected, approximately 40 hours per week.

• The role is remote, offering flexibility in how and where work is performed within the US.

• Occasional flexibility may be required to accommodate cross-functional team meetings across different time zones.

📝 Enhancement Note: The hourly rate of $70-$80 is competitive for experienced UX Designers with specialized skills in Conversational AI and Microsoft Copilot in the US market. The annual equivalent assumes a standard 40-hour work week for the duration of the contract. As this is a contractor position, explicit mention of typical employee benefits is omitted, but potential advantages of contracting are highlighted.

🎯 Team & Company Context

🏢 Company Culture

Industry: Technology Consulting / Digital Product Development. Ontrac Solutions partners with organizations to build scalable digital products and platforms, indicating a focus on innovation and client success within the tech sector.

Company Size: Information not directly provided, but the nature of their business (partnering with "elite organizations to build digital products") suggests they are likely a mid-sized to large consulting firm with a significant client base and project portfolio.

Founded: Specific founding date not provided, but their established presence and focus on modern digital product development imply they are a contemporary organization.

Team Structure:

• The UX Designer will likely be part of a project-based team, collaborating closely with Ontrac Solutions' internal project leads, as well as client-side product managers, engineers, and business stakeholders.

• The role requires working independently but also necessitates strong collaboration within a cross-functional team environment.

• Reporting will likely be to an Ontrac Solutions project manager or technical lead, with direct collaboration with client stakeholders. Methodology:

• Ontrac Solutions emphasizes building digital products and experiences at scale, suggesting a methodology grounded in agile development, human-centered design, and data-driven decision-making.

• The focus on "customer experience initiatives" and "thoughtful voice and chat-based experiences" points towards a design process that prioritizes user needs, business goals, and technical feasibility.

• Expect a methodology that involves iterative design, prototyping, user testing, and close collaboration with engineering for implementation.

Company Website: https://ontrac-solutions-llc.breezy.hr (Note: This appears to be an ATS portal, not the primary company website. A more direct company website would be beneficial if available, e.g., ontracsolutions.net.)

📝 Enhancement Note: The company description positions Ontrac Solutions as a strategic partner for digital transformation. The culture likely values innovation, client delivery, and technical expertise. The UX Designer will navigate both internal Ontrac processes and client-specific environments.

📈 Career & Growth Analysis

Operations Career Level: This role is positioned as a Mid-Level UX Designer, requiring 3-5 years of experience. It offers a significant opportunity to specialize in the rapidly growing field of Conversational AI and Microsoft Copilot.

Reporting Structure: The designer will report to an Ontrac Solutions project lead or manager, but will work very closely with client-side product management and engineering teams. This structure fosters direct exposure to client business challenges and technical implementation details.

Operations Impact: While not a traditional "Revenue Operations" role, this UX Designer will have a direct impact on the user experience of critical digital products. By creating intuitive and effective conversational interfaces, the designer will influence customer satisfaction, operational efficiency (through reduced support needs or faster task completion), and potentially adoption rates of AI-powered tools, all of which have downstream revenue implications.

Growth Opportunities:

• Specialization Deepening: Become a subject matter expert in Conversational AI design, particularly within the Microsoft ecosystem (Copilot). This niche skill set is in high demand.

• Cross-functional Leadership: Develop stronger skills in stakeholder management, workshop facilitation, and influencing product direction, potentially leading design initiatives on future projects.

• Mentorship: Gain experience mentoring junior designers, a key step towards senior or lead roles.

• Project Variety: As a contractor, the opportunity to work on diverse projects for different clients can broaden experience across various industries and technical challenges.

📝 Enhancement Note: This role offers specialized growth within UX design, focusing on AI. The contractor status means growth is often project-dependent but can be accelerated through high-impact contributions and skill development.

🌐 Work Environment

Office Type: Fully Remote. This role is designed for individuals who can work independently and effectively from their own workspace.

Office Location(s): While the role is remote, candidates must be based in the United States (US) to be considered. This is often due to client requirements, tax implications, or legal considerations for contracting.

Workspace Context:

• The primary workspace will be the designer's own home office or equivalent, requiring reliable internet access and a conducive environment for focused work.

• Collaboration will occur primarily through digital tools (e.g., video conferencing, Slack, Figma, project management software).

• Expect a dynamic environment where close digital collaboration with both Ontrac Solutions colleagues and client teams is essential. Work Schedule:

• Standard professional hours (approximately 40 hours per week) are expected.

• The remote nature allows for some flexibility in scheduling the workday, provided project deadlines and meeting commitments are met.

• Time zone coordination will be necessary for effective collaboration with teams potentially spread across the US.

📝 Enhancement Note: The remote aspect is a key feature, offering flexibility but demanding self-discipline and strong communication skills. The US-only requirement is a practical consideration for potential applicants.

📄 Application & Portfolio Review Process

Interview Process:

• Initial Screening: A brief call with a recruiter to assess basic qualifications, experience, and interest in the role.

• Technical Interview (Portfolio Review): A more in-depth interview with hiring managers or senior designers. This will heavily focus on reviewing your portfolio, discussing your past projects, design process, and specific experience with conversational AI and Figma. Expect to walk through case studies.

• Stakeholder/Team Interview: An interview with potential collaborators (e.g., product managers, engineers) to assess communication style, collaboration skills, and cultural fit within a project team.

• Final Interview/Offer: Potentially a final discussion with senior leadership or a formal offer.

Portfolio Review Tips:

• Curate for Conversational AI: Ensure your portfolio prominently features projects specifically related to voice, chat, virtual assistants, or AI interfaces.

• Showcase Figma Work: Be prepared to demonstrate your Figma proficiency, showcasing interactive prototypes, complex flows, and detailed design specifications.

• Detail Your Process: For each project, clearly articulate the problem, your role, your design process (ideation, research, design, testing), key decisions, and the outcomes/impact.

• Highlight Microsoft Copilot Experience: If you have direct experience with Copilot, make sure it's clearly presented and you can speak to its functionalities and design implications.

• Quantify Impact: Wherever possible, include metrics that demonstrate the success of your designs (e.g., improved task completion, reduced error rates, increased user satisfaction scores).

• Prepare for Dialogue Design: Be ready to discuss your approach to writing sample dialogs, developing personas, and structuring conversations for clarity and user engagement.

Challenge Preparation:

• Design Exercise: You may be given a small design challenge or asked to critique an existing conversational interface. Prepare to apply your design thinking and articulate your rationale clearly and concisely.

• Problem-Solving Scenarios: Be ready to discuss how you would approach ambiguous design problems or resolve conflicting stakeholder requirements.

• Technical Understanding: While not a developer role, demonstrate an understanding of how conversational AI works at a high level and the technical considerations that influence design.

📝 Enhancement Note: The portfolio review is the most critical part of the application process for this role. Candidates should tailor their portfolio to specifically highlight their conversational AI and Microsoft Copilot expertise, alongside their Figma skills.

🛠 Tools & Technology Stack

Primary Tools:

• Microsoft Copilot: Core platform for designing and integrating AI-driven conversational experiences.

• Figma: Essential tool for wireframing, prototyping, and creating detailed design artifacts. Proficiency is mandatory.

• Conversational AI Platforms: Experience with various platforms for building and deploying chatbots and virtual assistants is highly valuable.

• IVR Platforms: Familiarity with Interactive Voice Response systems and their design tools.

Analytics & Reporting:

• While not explicitly listed, an understanding of analytics related to user behavior in conversational interfaces (e.g., conversation completion rates, drop-off points, user satisfaction scores) is beneficial. Tools like Google Analytics, Mixpanel, or specialized conversational analytics platforms may be used by client teams. CRM & Automation:

• Understanding how conversational AI can integrate with CRM systems (e.g., Salesforce, Dynamics 365) and automation workflows is a plus, especially when designing enterprise solutions.

📝 Enhancement Note: Figma and Microsoft Copilot are the absolute core tools for this role. Any experience with related AI platforms, VUI design tools, or CRM integrations will be a significant advantage.

👥 Team Culture & Values

Operations Values:

• User-Centricity: A deep commitment to understanding and advocating for the end-user in all design decisions.

• Collaboration: A strong emphasis on working effectively within cross-functional teams, valuing diverse perspectives, and fostering open communication.

• Innovation: A drive to explore and implement cutting-edge AI and UX solutions to solve complex problems.

• Efficiency & Scalability: Designing solutions that are not only user-friendly but also technically feasible, scalable, and contribute to business efficiency.

• Data-Driven Design: Utilizing qualitative and quantitative data to inform design choices and measure impact.

Collaboration Style:

• Cross-functional Integration: Expect to work closely with product managers, engineers, AI specialists, and business stakeholders, requiring clear and concise communication.

• Iterative Design Process: Collaboration will likely involve frequent feedback loops, design reviews, and iterative adjustments based on input from various team members.

• Knowledge Sharing: A culture that encourages sharing insights, best practices, and lessons learned, especially within the specialized field of conversational AI.

📝 Enhancement Note: The culture likely values a blend of technical expertise, creative problem-solving, and strong interpersonal skills necessary for client-facing consulting work.

⚡ Challenges & Growth Opportunities

Challenges:

• Balancing User Needs with Technical Constraints: Designing effective conversational AI often involves navigating limitations in current AI technology, complex backend systems, and budget constraints.

• Stakeholder Alignment: Gaining consensus among diverse stakeholders (e.g., technical teams, business units, marketing) with potentially differing priorities can be challenging.

• Rapidly Evolving Technology: Staying current with the fast pace of AI development, particularly within the Microsoft ecosystem, requires continuous learning.

• Measuring Conversational ROI: Quantifying the direct business impact and return on investment for conversational AI features can be complex.

Learning & Development Opportunities:

• Deep Dive into Microsoft AI: Gain extensive experience with Microsoft Copilot and other Azure AI services, becoming an expert in designing for this ecosystem.

• Specialized Conversational Design: Develop advanced skills in NLU, dialogue management, and VUI design patterns.

• Cross-Industry Exposure: Work on projects for various clients, providing exposure to different business challenges and user bases.

• Contracting Skills: Develop skills in client management, proposal contribution, and project scoping within a consulting framework.

📝 Enhancement Note: This role offers significant opportunities to become an expert in a high-demand field, with challenges inherent to cutting-edge technology and client-focused consulting.

💡 Interview Preparation

Strategy Questions:

• "Describe your process for designing a conversational flow for a complex customer service task. How would you ensure it's intuitive and efficient?" (Focus on your structured approach, user-centricity, and iterative testing.)

• "Walk me through a conversational AI project you're particularly proud of. What were the key challenges, your specific contributions, and the outcome?" (Prepare a detailed case study highlighting your role, design decisions, and measurable results.)

• "How would you approach designing for Microsoft Copilot specifically? What are the unique considerations compared to other conversational platforms?" (Showcase your understanding of Copilot's capabilities and limitations.)

• "Imagine a stakeholder wants to implement a feature that is technically infeasible or detrimental to the user experience. How would you handle this situation?" (Demonstrate your negotiation, communication, and user advocacy skills.) Company & Culture Questions:

• "What interests you about Ontrac Solutions and this specific role?" (Research Ontrac Solutions and articulate how your skills align with their mission and the project’s goals.)

• "How do you typically collaborate with product managers and engineers on design projects?" (Highlight your teamwork, communication, and ability to integrate design into the SDLC.)

• "How do you stay updated on the latest trends in conversational AI and UX design?" (Show your commitment to continuous learning and industry awareness.) Portfolio Presentation Strategy:

• Structure: Organize your portfolio logically, perhaps by project type or by showcasing your most relevant conversational AI work first.

• Narrative: For each project, tell a compelling story: the problem, your approach, your role, the design process, key decisions, and the impact.

• Visuals: Use clear visuals, including wireframes, flow diagrams, prototypes (live demos if possible), and screenshots.

• Conciseness: Be prepared to present key aspects of your work efficiently, focusing on what’s most relevant to this role.

• Figma Demos: If possible, be ready to briefly demo a Figma prototype live to showcase your interactive design skills.

📝 Enhancement Note: Expect interview questions that probe your design process, problem-solving abilities, and specific experience with conversational AI and Microsoft Copilot. A well-prepared portfolio is your strongest asset.

📌 Application Steps

To apply for this UX Designer position:

• Submit your application through the provided Breezy HR link.

• Tailor your resume: Highlight keywords such as "Conversational AI," "Microsoft Copilot," "Figma," "VUI," "Interaction Design," "User Flows," and "SDLC." Quantify achievements wherever possible.

• Prepare your portfolio: Ensure it prominently features conversational AI projects, showcases your Figma skills, and clearly articulates your design process and impact. Be ready to present specific case studies.

• Research Ontrac Solutions: Understand their business, client focus, and the type of digital products they build.

• Practice your pitch: Be ready to articulate your experience, suitability for the role, and enthusiasm during interviews, especially during the portfolio review.

⚠️ Important Notice: This enhanced job description provides a comprehensive overview based on the provided information and industry standards. Specific details regarding project scope, client, and exact deliverables may vary. Candidates are encouraged to ask clarifying questions during the interview process.