Senior Frontend Software Engineer, AI UX

📍 Job Overview

Job Title: Senior Frontend Software Engineer, AI UX

Company: Pebl

Location: Toronto, Ontario, Canada

Job Type: Full-Time

Category: Software Engineering / AI UX

Date Posted: September 1, 2026

Experience Level: Senior (8+ years professional experience)

Remote Status: Telecommute (Remote within Canada)

🚀 Role Summary

• Drive the user-facing AI experience for Pebl's conversational AI assistant, Alfie, with a strong emphasis on frontend and UX innovation.

• Design and implement full-stack features, leveraging hands-on experience with LLM-based and agentic systems to create intuitive and effective AI interactions.

• Contribute to the definition of AI-native user experiences, pushing the boundaries of conversational interfaces beyond existing playbooks.

• Collaborate with a team focused on shaping the future of how users interact with software, particularly in the rapidly evolving AI landscape.

• Ensure high engineering standards through clean code, robust API design, and thorough code reviews across the technology stack.

📝 Enhancement Note: This role is specifically focused on the user-facing aspects of AI, differentiating it from backend AI infrastructure or internal tooling roles. The emphasis is on product engineering and the direct user interaction with AI, particularly conversational interfaces. The "Senior" title, coupled with the 8+ years of experience requirement and the focus on innovation, suggests a significant impact on product direction and technical leadership within the AI UX domain.

📈 Primary Responsibilities

• Design, develop, and deploy full-stack features for Pebl's conversational AI assistant, with a primary focus on frontend implementation and user experience.

• Integrate LLM-based and agentic system concepts, including prompt design, tool/function calling, and multi-step reasoning, to enhance the AI assistant's behavior and UI presentation.

• Champion and implement innovative interaction patterns for conversational and generative AI interfaces, adapting to advancements in underlying AI models.

• Proactively identify and address user trust, fallback states, streaming response handling, and human-in-the-loop moments within the AI UX.

• Build and maintain clean, scalable, and maintainable code across the full stack, ensuring seamless integration between frontend and backend services.

• Mentor junior engineers, foster a culture of continuous learning, and contribute to code reviews to uphold engineering quality and best practices.

• Troubleshoot and resolve end-to-end production issues, including AI-specific challenges like suboptimal model outputs, latency, and API integration failures.

• Participate actively in technical discussions, architectural reviews, and strategic planning for AI UX development.

📝 Enhancement Note: The responsibilities highlight a blend of hands-on development and strategic thinking. The emphasis on "pushing the boundaries" and "discovering patterns" indicates a role that requires creativity and a proactive approach to innovation in AI UX, rather than just execution of predefined tasks. The inclusion of production troubleshooting for AI-specific issues underscores the need for deep understanding of both software engineering and AI system behavior.

🎓 Skills & Qualifications

Education: While no specific degree is listed, a strong educational foundation in Computer Science, Software Engineering, or a related technical field is implied by the experience requirements and the nature of the role.

Experience: Minimum of 8+ years of professional software engineering experience, with a demonstrated preference and strength in frontend/UX development. A strong understanding of full-stack development is also essential.

Required Skills:

• 8+ years of professional software engineering experience.

• Demonstrated strength and preference for frontend/UX development.

• 1+ years of hands-on experience building LLM-powered or agentic products (e.g., designing agent reasoning, tool usage, user handoffs).

• Experience building interfaces for AI-powered or agentic products, including conversational UIs, copilots, or assistants.

• Solid understanding of LLM design patterns, prompt engineering, and observability/instrumentation for agentic systems.

• Strong command of modern frontend technologies, specifically React and TypeScript.

• Proficient in integrating frontend applications with backend services, APIs, and real-time/streaming data.

• Experience building products with a distinctive user experience beyond standard CRUD applications.

• Comfort working across the full stack, including backend development and infrastructure considerations.

• A lean mindset focused on customer value, workflow optimization, and continuous improvement.

• Enthusiasm for working in a rapidly evolving AI space and contributing to the discovery of new UX patterns. Preferred Skills:

• Experience with generative/dynamic UI techniques where the interface adapts to model behavior.

• Proven track record of developing products with significant craft, polish, or a distinctive user experience.

• Experience mentoring junior engineers and fostering a culture of learning.

• Familiarity with agile development methodologies and quick iteration cycles.

📝 Enhancement Note: The experience requirement of "8+ years" with a "clear preference for frontend/UX work" combined with "1+ years of hands-on experience building LLM-powered or agentic products" suggests a need for a seasoned engineer who can bridge deep frontend expertise with emerging AI capabilities. The emphasis on "not just calling an API" indicates a requirement for understanding the underlying mechanics and user implications of AI agent behavior.

📊 Process & Systems Portfolio Requirements

Portfolio Essentials:

• Demonstrations of complex frontend applications with a focus on user experience and intuitive design.

• Examples of full-stack projects that showcase integration capabilities between frontend and backend systems.

• Case studies detailing the development of AI-powered features or interfaces, highlighting the application of LLM concepts or agentic workflows.

• Projects that exhibit a strong product taste and a focus on polish and distinctive user experiences beyond standard applications.

• Evidence of work involving real-time data streaming or dynamic UI elements that respond to backend logic or model outputs. Process Documentation:

• Showcase of how you approach problem-solving and translate complex requirements into functional, user-centric features.

• Examples of contributions to technical design documents, API contracts, and system architecture discussions.

• Documentation or presentation of how you've troubleshot and resolved complex technical issues, particularly those involving AI components or real-time data.

• Evidence of participation in code reviews, demonstrating an ability to provide constructive feedback and maintain code quality.

📝 Enhancement Note: For a role focused on AI UX, a portfolio should strongly emphasize the user-facing aspects of AI. This means showcasing projects where the engineer has significantly influenced the user's interaction with AI, rather than just implementing a backend model. Demonstrating an understanding of how AI behavior translates into a seamless and engaging user experience is crucial.

💵 Compensation & Benefits

Salary Range: The stated salary range for this position is CAD $140,000 - $200,000 per year.

Benefits:

• Flexible Time Off: Encourages employees to take the time they need to recharge.

• Parental Leave: Comprehensive support for new parents.

• Health and Dental Insurance: Provided where applicable, covering employees and their dependents.

• Retirement Savings + Employee Incentive Plan: Support for long-term financial planning and a share in company success.

• Equity: Implied as a potential component of the overall compensation package.

Working Hours: The standard working hours are estimated at 40 hours per week, aligning with full-time employment. The remote nature of the role offers flexibility in how these hours are managed, within reasonable operational needs.

📝 Enhancement Note: The salary range of CAD $140,000 - $200,000 is competitive for a Senior Frontend Software Engineer role with specialized AI UX experience in Toronto. This range reflects the high demand for engineers skilled in both cutting-edge frontend development and emerging AI technologies. The benefits package is comprehensive, supporting work-life balance, health, and financial well-being, which are key considerations for senior-level talent.

🎯 Team & Company Context

🏢 Company Culture

Industry: Technology, specifically focused on Global Employment Platforms and AI-driven solutions. Pebl operates within the HR Tech and AI sectors, aiming to simplify global hiring and management.

Company Size: While not explicitly stated, the company description and the breadth of their AI initiatives suggest a growing, dynamic organization. The emphasis on "scaling faster, competing harder" implies a scale-up environment.

Founded: Pebl has "more than a decade of compliance leadership," indicating an established company with significant experience in the global employment space, likely founded before 2013.

Team Structure:

• The role is within the "AI & Knowledge team," specifically working on "Alfie," the conversational AI assistant.

• This team is at the forefront of developing AI-native user experiences, suggesting a collaborative and innovative environment.

• Collaboration is expected to be cross-functional, involving product, design, and engineering teams.

• The role includes mentoring junior team members, indicating a structure that supports knowledge sharing and leadership development. Methodology:

• Data-Driven AI UX: Focus on shaping AI experiences based on user interaction and feedback, with an emphasis on "real users."

• Lean Mindset & Agile Iteration: Prioritizing customer value, minimizing waste, and quick iteration cycles with rapid feedback.

• Innovation & Discovery: Actively seeking and defining new interaction patterns for AI, rather than following established playbooks.

• Full-Stack Development: Integrating frontend and backend components to support complex agentic workflows and real-time data.

Company Website: https://hellopebl.com/

📝 Enhancement Note: Pebl's mission to "simplify global employment" with an "AI-powered Global Work Platform" positions them as a leader in leveraging technology for complex business challenges. The company culture appears to value impact, innovation, and a lean, agile approach, which are critical for success in the fast-paced AI domain. The "Purpose in Every Position" tagline suggests a strong mission-driven ethos.

📈 Career & Growth Analysis

Operations Career Level: This is a Senior-level individual contributor role within the Software Engineering discipline, with a specialization in AI UX. It demands significant technical expertise, product intuition, and the ability to influence technical direction.

Reporting Structure: The role is within the "AI & Knowledge team" and likely reports to an Engineering Manager or Head of AI/Product. The emphasis on mentoring suggests a path towards technical leadership or principal engineer roles.

Operations Impact: This role has a direct impact on how Pebl's core AI product, Alfie, is perceived and utilized by customers. By defining and building the AI-native user experience, the engineer will significantly influence user adoption, satisfaction, and the overall value proposition of Pebl's platform. Success in this role contributes directly to Pebl's competitive advantage in the AI and global employment markets.

Growth Opportunities:

• Technical Leadership: Opportunity to become a subject matter expert in AI UX, leading technical design and strategy for new AI features.

• Mentorship & Team Building: Develop leadership skills by mentoring junior engineers and contributing to the growth of the AI & Knowledge team.

• Specialization in Emerging AI: Deepen expertise in cutting-edge areas like conversational AI, agentic systems, and generative UI, which are highly in-demand skills.

• Product Influence: Directly shape the user experience of a key product, influencing its roadmap and market success.

• Career Progression: Potential to move into Principal Engineer, Staff Engineer, or Architect roles, or transition into management if desired.

📝 Enhancement Note: The role is positioned at a senior level, implying a high degree of autonomy and influence. The growth opportunities are geared towards deepening technical expertise in a rapidly advancing field and taking on leadership responsibilities, aligning with typical career trajectories for senior engineers in innovative tech companies.

🌐 Work Environment

Office Type: The job is listed as "TELECOMMUTE" with a primary location in Toronto, Ontario, Canada, and the ability to work remotely within Canada. This indicates a remote-first or hybrid-flexible work environment.

Office Location(s): While the role is remote, the company is headquartered in Toronto, Ontario, Canada. This suggests that team members may be located across Canada, with potential for occasional in-person meetups or team events in Toronto.

Workspace Context:

• Remote Collaboration: Expect a highly collaborative environment facilitated by digital tools for communication, project management, and code sharing.

• Access to Technology: The company likely provides necessary hardware and software, including access to cloud-based development environments and AI/ML platforms.

• Team Interaction: Opportunities for interaction will be through virtual meetings, Slack channels, code reviews, and potentially virtual social events.

Work Schedule: The role is full-time, typically requiring around 40 hours per week. The remote nature allows for flexibility in scheduling, enabling engineers to manage their time effectively, provided they can collaborate with colleagues across different time zones and meet project deadlines.

📝 Enhancement Note: The "TELECOMMUTE" designation for Canada implies that the company is set up to support remote employees effectively. This environment is ideal for experienced engineers who are self-motivated and adept at asynchronous communication and remote collaboration.

📄 Application & Portfolio Review Process

Interview Process:

• Initial Screening: A review of your resume and portfolio for relevant experience in frontend, full-stack, and AI UX development.

• Technical Interview(s): Likely includes coding challenges (frontend and potentially full-stack), discussions on system design, LLM/agentic system concepts, and problem-solving scenarios. Expect questions that probe your understanding of AI UX patterns and your approach to building them.

• Portfolio Presentation/Discussion: A dedicated session to walk through your portfolio, explaining key projects, your contributions, technical decisions, and the impact of your work, especially concerning AI-driven features.

• Behavioral/Cultural Fit Interview: Assessment of your alignment with Pebl's values (e.g., lean mindset, innovation, collaboration) and your ability to mentor and contribute to team culture.

• Final Round/Hiring Manager Interview: A discussion with the hiring manager or senior leadership to assess overall fit, strategic thinking, and long-term potential.

Portfolio Review Tips:

• Highlight AI UX Impact: Focus on projects where you directly influenced the user experience of AI features. Quantify impact where possible (e.g., improved user engagement, reduced error rates).

• Showcase Frontend Craftsmanship: Demonstrate strong UI/UX design principles, clean code (React/TypeScript), and responsiveness in your frontend examples.

• Detail LLM/Agentic System Integration: Clearly explain your role in designing or implementing agent reasoning, prompt engineering, or dynamic UI elements driven by AI.

• Explain Technical Decisions: Be prepared to articulate why you made certain technical choices, the trade-offs involved, and how they contributed to the final product.

• Present End-to-End Solutions: If possible, showcase projects that demonstrate your ability to work across the full stack, from UI to API design.

Challenge Preparation:

• Coding Challenges: Practice common frontend challenges (component building, state management, API integration) and full-stack scenarios.

• System Design: Prepare for questions on designing scalable systems, API design, and architecting features for AI-driven applications.

• AI UX Scenarios: Think about how you would design the UX for specific AI interactions (e.g., handling incorrect AI responses, building trust in AI, designing conversational flows).

• Behavioral Questions: Prepare examples using the STAR method (Situation, Task, Action, Result) to illustrate your experience with collaboration, problem-solving, mentorship, and dealing with ambiguity.

📝 Enhancement Note: The interview process will likely probe both deep technical skills in frontend development and emerging expertise in AI UX. A strong portfolio that clearly articulates the candidate's impact on user experience with AI is essential. Expect challenges that require you to think critically about the intersection of technology and user interaction in the AI space.

🛠 Tools & Technology Stack

Primary Tools:

• Frontend: React, TypeScript.

• Backend: Comfortable working with backend components and APIs to support agentic workflows. Specific backend languages/frameworks are not explicitly stated but likely involve Node.js or similar for API development.

• AI/LLM Interaction: Experience with LLM APIs, prompt engineering techniques, and potentially frameworks for building agentic systems.

Analytics & Reporting:

• While specific tools aren't listed, expect the use of analytics platforms to track user engagement with AI features and performance metrics.

• Tools for monitoring AI model performance, latency, and error rates will be crucial for troubleshooting. CRM & Automation:

• Not explicitly mentioned as a primary focus for this role, but understanding how frontend applications integrate with broader platform services (which might include CRM or automation tools) is beneficial.

• Tools for real-time data streaming and dynamic UI updates are implied.

📝 Enhancement Note: The explicit mention of React and TypeScript for the frontend, coupled with the need for backend integration and LLM/agentic system experience, defines the core technical stack. The emphasis is on building robust, interactive user interfaces that leverage AI capabilities.

👥 Team Culture & Values

Operations Values:

• Purpose in Every Position: A strong emphasis on contributing to the company's mission of simplifying global employment through technology and AI.

• Accountability for Results and Impact: Team members are expected to drive success and be accountable for their contributions.

• Innovation and Discovery: A culture that encourages pushing boundaries, exploring new possibilities, and creating novel AI-driven user experiences.

• Lean Mindset: Focus on delivering customer value efficiently, minimizing waste, and fostering continuous improvement through quick iterations and feedback.

• Collaboration Across Borders: Working effectively in a global, remote-first environment, valuing diverse perspectives.

Collaboration Style:

• Cross-functional Integration: Close collaboration with product managers, designers, and other engineers to define and build AI UX features.

• Mentorship and Knowledge Sharing: An environment where senior engineers are expected to mentor junior team members and share best practices.

• Constructive Feedback: A culture that values open communication, constructive code reviews, and technical discussions to maintain high engineering standards.

• Agile and Iterative: Working in sprints with a focus on rapid prototyping, testing, and incorporating feedback to refine AI interactions.

📝 Enhancement Note: The company culture at Pebl appears to be mission-driven, innovative, and focused on execution. The values of purpose, accountability, and a lean mindset are central to how the team operates, especially within the dynamic AI space.

⚡ Challenges & Growth Opportunities

Challenges:

• Rapidly Evolving AI Landscape: Keeping pace with the continuous advancements in LLMs, agentic systems, and AI UX patterns requires ongoing learning and adaptation.

• Defining Novel AI UX: The challenge of creating new, effective, and intuitive user experiences for AI where established patterns are still emerging.

• Balancing Innovation with Production Stability: Ensuring that cutting-edge AI features are robust, reliable, and performant in a production environment.

• Integrating AI Complexity into User Interfaces: Translating complex AI behaviors (e.g., multi-step reasoning, tool use) into simple, understandable, and actionable user interactions.

Learning & Development Opportunities:

• Deep Dive into AI UX: Gain unparalleled experience in shaping the future of conversational and generative AI interfaces.

• Exposure to Cutting-Edge AI: Work directly with advanced LLM technologies and agentic system architectures.

• Technical Leadership Development: Opportunities to lead technical initiatives, mentor junior engineers, and influence product strategy.

• Industry Conferences and Research: Potential to attend relevant AI and UX conferences or engage with industry research to stay at the forefront of the field.

📝 Enhancement Note: This role presents a significant opportunity to be at the leading edge of AI UX development. The challenges are inherent to working in a nascent field, offering substantial learning and growth potential for ambitious engineers.

💡 Interview Preparation

Strategy Questions:

• "Describe a time you had to design a user experience for a complex, non-deterministic system. How did you ensure user trust and clarity?" (Focus on AI UX, error handling, transparency).

• "How would you approach designing the UX for an AI assistant that needs to perform multi-step reasoning and call various tools? What are the key UI considerations?" (Probe understanding of agentic workflows, user feedback loops).

• "Imagine our AI assistant provides a response that is factually incorrect or unhelpful. What steps would you take from a UX perspective to mitigate this, and how would you design a feedback mechanism?" (Test problem-solving for AI failures, user feedback integration). Company & Culture Questions:

• "Pebl values a 'lean mindset.' How have you applied lean principles in your previous engineering roles?" (Look for examples of efficiency, waste reduction, rapid iteration).

• "What excites you most about the potential of AI-native user experiences, and how do you see them evolving in the next 3-5 years?" (Assess passion for the field, forward-thinking).

• "Describe a situation where you had to push back on a product direction or technical decision. How did you handle it, and what was the outcome?" (Evaluate communication, influence, and ability to advocate for technical or UX best practices). Portfolio Presentation Strategy:

• Structure your AI UX Projects: For each relevant project, clearly articulate the problem, your specific role (especially in influencing the AI interaction), the technologies used, the challenges faced, and the measurable impact on the user experience.

• Demonstrate the 'Craft': Show, don't just tell, the polish and distinctiveness of your work. Highlight specific UI elements, animations, or interaction flows that made the user experience exceptional.

• Explain the 'Why': For every design choice, be ready to explain the rationale, especially how it relates to AI behavior or user psychology.

• Prepare for Live Coding/Whiteboarding: Be ready to translate a small AI UX concept or feature into code or a design on the spot, demonstrating your problem-solving skills and coding fluency.

📝 Enhancement Note: Interview preparation should focus on bridging your frontend expertise with your understanding of AI capabilities and user interaction. Be ready to articulate your vision for AI UX and back it up with concrete examples and thoughtful reasoning.

📌 Application Steps

To apply for this Senior Frontend Software Engineer, AI UX position:

• Submit your application through the provided link on Ashby.

• Tailor your Resume: Emphasize your 8+ years of professional software engineering experience, specifically highlighting your strengths in React, TypeScript, and frontend/UX development. Quantify achievements where possible.

• Curate Your Portfolio: Select 2-3 projects that best showcase your experience in building complex frontend applications, particularly those involving AI/LLM integration, conversational interfaces, or distinctive user experiences. Prepare to walk through these projects in detail.

• Prepare for Technical Screening: Brush up on React, TypeScript, JavaScript fundamentals, and common frontend architectural patterns. Be ready to discuss LLM concepts and agentic systems from a UX perspective.

• Research Pebl: Understand Pebl's mission, their Global Work Platform, and their AI assistant, Alfie. Familiarize yourself with their values and consider how your experience aligns with their innovative approach to AI UX.

⚠️ Important Notice: This enhanced job description includes AI-generated insights and operations industry-standard assumptions. All details should be verified directly with the hiring organization before making application decisions.