Senior Product Designer

📍 Job Overview

Job Title: Senior Product Designer

Company: Mycroft

Location: Toronto, Ontario, Canada

Job Type: FULL_TIME

Category: Product Design / UX/UI

Date Posted: 2026-08-11

Experience Level: Senior (5-10 years)

Remote Status: Hybrid (2-3 days in office per week)

🚀 Role Summary

• Own and drive the design strategy for complex, expert-facing workflows within an AI-native security and compliance platform, focusing on information density, state clarity, and trust.

• Define and uphold the design system, patterns, and quality standards for all product design at Mycroft, proposing and defending what constitutes "good" design.

• Ensure high design-to-build fidelity by collaborating closely with engineers through the implementation phase, understanding when to prioritize polish versus rapid iteration.

• Mentor a junior designer, raising the overall design bar through critique, pairing, and establishing rigorous standards.

• Leverage AI tooling as a force multiplier for design processes, while ensuring accountability for the clarity and defensibility of design decisions.

📝 Enhancement Note: While the original job title is "Senior Product Designer," the description emphasizes deep ownership of complex B2B workflows, design system evolution, and team mentorship, aligning it with a senior or lead product designer role within an operations-focused technology company. The role requires a strong understanding of how design impacts critical business functions like security and compliance.

📈 Primary Responsibilities

• Tackle complex design challenges in expert-facing workflows, including frameworks, controls, evidence management, and risk quantification, where design decisions have direct compliance and security outcomes.

• Lead the evolution and maintenance of Mycroft's design system, establishing and advocating for best practices in UI patterns, component libraries, and overall design quality.

• Collaborate closely with engineering teams to ensure seamless implementation of designs, providing clear specifications and actively participating in the build process to maintain design integrity.

• Mentor and guide a junior designer, fostering their growth through constructive feedback, collaborative design sessions, and by setting high standards for design output.

• Actively engage with forward-deployed engineers (FDEs) and customers to gain deep domain expertise in security and compliance, translating real-world practitioner needs into intuitive design solutions.

• Utilize and advocate for effective use of AI tooling to accelerate design processes, while maintaining rigorous standards for clarity, accuracy, and defensibility of design outputs.

• Propose and defend design decisions based on a thorough understanding of the security and compliance domain, user workflows, and the impact of design on customer trust and outcomes.

📝 Enhancement Note: The responsibilities are framed around ownership and leadership within the design function, emphasizing the strategic impact of design on the core product offering, which is crucial for a security and compliance platform. The inclusion of "forward-deployed engineers" suggests a hands-on approach to understanding user needs in a highly technical domain.

🎓 Skills & Qualifications

Education: While no specific degree is mandated, a strong portfolio demonstrating equivalent knowledge and experience in product design is essential. An appetite for learning the intricacies of the security and compliance domain is highly valued.

Experience: 6+ years of product design experience with a proven track record of owning complex B2B or expert-tooling surfaces. Experience with data-heavy, workflow-heavy, regulated, or infrastructure products is critical.

Required Skills:

• Demonstrated expertise in designing complex B2B or expert-facing software interfaces.

• Proven ability to develop and significantly evolve a design system in a production environment.

• Strong skills in information architecture and understanding state logic within complex applications.

• Proficiency in Figma for design, prototyping, and system documentation.

• Experience in choosing and utilizing appropriate artifacts (diagrams, prototypes, static handoffs) for effective communication and collaboration.

• Ability to mentor junior designers, elevate team standards, and conduct effective design critiques.

• Excellent collaboration skills with engineering teams, including naming states, identifying edge cases, and negotiating scope.

• Professional fluency in English.

• Legal authorization to work in Canada. Preferred Skills:

• Experience in regulated domains such as security, compliance, or finance.

• Hands-on experience with AI tooling to enhance design workflows.

• Familiarity with security and compliance frameworks (e.g., SOC 2, FedRAMP, CMMC, PCI-DSS).

• Experience with user research methodologies and translating findings into design solutions.

• Understanding of technical documentation and its role in user comprehension.

📝 Enhancement Note: The emphasis on "information architecture and state logic underneath the screens" rather than just polish, and the requirement to have "built or meaningfully evolved a design system in production," are key differentiators for senior-level product design roles, especially in complex B2B environments. The mention of AI tooling as a standard part of the workflow is also a significant trend.

📊 Process & Systems Portfolio Requirements

Portfolio Essentials:

• Showcase detailed information architecture diagrams and explanations of state logic for complex B2B or expert-tooling applications.

• Present case studies demonstrating ownership of challenging design problems within data-heavy, workflow-intensive, regulated, or infrastructure products.

• Include evidence of building or significantly evolving a production design system, detailing its components, patterns, and impact.

• Demonstrate a clear understanding of the design-to-build process, illustrating how designs were translated into functional products and how trade-offs were managed.

• Highlight experience with AI tooling and how it was integrated into the design process to enhance efficiency or outcomes. Process Documentation:

• Detail the process for defining and documenting complex user workflows, including how user needs and domain expertise were incorporated.

• Explain methodologies used for creating and maintaining design systems, including governance, contribution, and evolution strategies.

• Illustrate the approach to collaborating with engineering teams through the implementation phase, including handoff procedures, feedback loops, and problem-solving.

• Provide examples of how design decisions were defended and how trade-offs between polish, speed, and scope were managed.

📝 Enhancement Note: The portfolio requirements are highly specific, prioritizing depth in information architecture, state logic, and design system maturity over superficial polish. This indicates a need for a designer who understands the underlying structure and logic of complex systems, which is crucial for a security and compliance platform.

💵 Compensation & Benefits

Salary Range: $100,000 - $140,000 CAD per year. This range is based on the provided information and aligns with senior-level product design roles in Toronto, considering the company's growth stage and the specialized nature of the product.

Benefits:

• Competitive salary and equity package.

• Health and dental coverage.

• Monthly tooling stipend for productivity tools, including AI subscriptions and design software.

• Support for work-from-home arrangements.

• Opportunities for professional development and growth within a fast-paced startup environment.

Working Hours: Standard full-time hours (estimated at 40 hours per week), with a hybrid work arrangement supporting flexibility. The company emphasizes autonomy and trusts individuals to manage their time effectively to deliver high-quality work.

📝 Enhancement Note: The salary range is explicitly provided. The inclusion of equity and a tooling stipend, especially for AI subscriptions, points to a forward-thinking startup environment that invests in its employees' productivity and growth. The hybrid model with expected office days is clearly stated.

🎯 Team & Company Context

🏢 Company Culture

Industry: AI-Native Security and Compliance Platform. Mycroft operates at the intersection of Artificial Intelligence, Cybersecurity, and Regulatory Compliance, a rapidly growing and critical sector. The company aims to make continuous compliance accessible through a combination of AI agents and human expertise, disrupting traditional, costly consulting models.

Company Size: Early-stage startup (implied by "small team," "what you own is genuinely yours," and rapid revenue growth). This suggests a dynamic, fast-paced environment where individual contributions have significant impact.

Founded: Information not explicitly provided, but the company's rapid growth ("doubled revenue in the past six months and are on track to grow revenue 5x this year") indicates it's past the initial seed stage and is experiencing significant traction.

Team Structure:

• The product team is small and led by a co-founder who is actively involved in design and shipping.

• Designers will work in close lockstep with Engineering and Forward-Deployed Engineers (FDEs).

• FDEs are described as running customer compliance programs hands-on, indicating a unique, integrated role that bridges product, customer success, and domain expertise. Methodology:

• Data-Driven Design: Emphasis on creating designs that are not only aesthetically pleasing but also highly functional and trustworthy, particularly for expert users.

• Agile & Iterative: Moving fast and shipping work continuously, while maintaining rigor and quality. The company values individuals who can be both fast and rigorous.

• Domain Immersion: Designers are expected to gain subject-matter expertise in security and compliance by engaging in "real FDE work on live customer implementations."

• AI Integration: AI tools are a standard part of the workflow, not a hidden secret, but accountability for design quality remains with the designer.

Company Website: https://mycroft.io

📝 Enhancement Note: The company culture is characterized by speed, rigor, and deep domain immersion. The unique role of FDEs suggests a highly collaborative and hands-on approach to product development, where designers are expected to become experts in the security and compliance domain.

📈 Career & Growth Analysis

Operations Career Level: Senior Product Designer. This role is positioned as a senior individual contributor with significant ownership and influence. It involves not only executing design tasks but also setting standards, evolving the design system, and mentoring junior talent. The role requires a blend of strategic thinking, tactical execution, and leadership within the design function.

Reporting Structure: The designer will report to a co-founder who leads the product team and is still actively involved in design. This implies direct access to leadership and a less bureaucratic reporting hierarchy, common in early-stage companies. Collaboration will be tight with Engineering and Forward-Deployed Engineers (FDEs).

Operations Impact: The designer's work will have a direct and substantial impact on Mycroft's core product offering. By owning critical design problems in security and compliance workflows, the designer will influence customer trust, product adoption, and ultimately, the company's ability to achieve its ambitious revenue growth targets. The emphasis on "information density, state clarity, and trust" as the product highlights the critical nature of design in this domain.

Growth Opportunities:

• Leadership Development: Opportunity to mentor a junior designer and potentially shape the future of the design team as the company scales.

• Domain Expertise: Deep dive into the security and compliance industry, becoming a subject matter expert, which is a highly valuable specialization.

• Product Ownership: Take significant ownership of key product areas, directly influencing product strategy and roadmap.

• Skill Expansion: Opportunity to work with cutting-edge AI tooling and contribute to the evolution of a design system in a rapidly growing tech company.

• Career Progression: Potential to move into a Design Lead or Head of Design role as the company expands.

📝 Enhancement Note: The growth opportunities are significant for a senior role in an early-stage company, focusing on leadership, domain specialization, and direct product impact, which are attractive to ambitious operations and product professionals.

🌐 Work Environment

Office Type: Hybrid model with a downtown Toronto office. The company supports both in-office collaboration and remote work, suggesting a flexible approach to work arrangements. The majority of the team is expected to be in the office 2-3 days per week.

Office Location(s): Downtown Toronto office. This location is strategic for talent acquisition and offers accessibility for employees. Specific details on office amenities or layout are not provided, but a downtown location typically implies a professional business environment.

Workspace Context:

• Collaborative Environment: The hybrid model encourages in-person collaboration for core team members, fostering a sense of community and facilitating spontaneous problem-solving.

• Tooling & Technology: Employees receive a tooling stipend to customize their workspace with preferred AI subscriptions, design tools, and other productivity enhancers. This indicates a commitment to providing the best resources for employees.

• Cross-functional Interaction: Designers will work closely with engineers and FDEs, offering ample opportunities for cross-functional learning and interaction. The "real FDE work" suggests a deeply integrated experience with customer-facing operations.

Work Schedule: Full-time, with flexibility offered through the hybrid model. While 2-3 days are expected in the office, the overall work schedule is likely adaptable, allowing individuals to manage their time effectively to meet project demands. The emphasis on autonomy suggests a results-oriented culture.

📝 Enhancement Note: The hybrid model is clearly defined with specific expectations for office days. The tooling stipend is a strong indicator of the company's investment in employee productivity and a flexible work environment.

📄 Application & Portfolio Review Process

Interview Process:

• Initial Screening: Review of resume and portfolio to assess alignment with experience and skills.

• Portfolio Presentation & Discussion: Candidates will likely present their portfolio, focusing on specific case studies that demonstrate ownership of complex B2B workflows, design system contributions, and problem-solving abilities. Expect questions about information architecture, state logic, and design-to-build fidelity.

• Design Challenge/Exercise: A practical exercise may be given, potentially involving a design problem related to security, compliance, or expert workflows, to assess problem-solving skills, design process, and use of AI tools.

• Cross-functional Interviews: Meetings with engineering leads, FDEs, and potentially other team members to evaluate collaboration style, technical understanding, and cultural fit.

• Founder/Leadership Interview: Final discussion with leadership to assess strategic thinking, alignment with company vision, and overall fit.

Portfolio Review Tips:

• Highlight Ownership: Clearly articulate your role and level of ownership in each project, especially for complex B2B or expert-tooling surfaces.

• Showcase Process, Not Just Polish: Include diagrams, wireframes, state logic explanations, and design system documentation. Demonstrate how you arrived at the final design.

• Quantify Impact: If possible, provide metrics or qualitative feedback that demonstrate the impact of your design solutions on user outcomes or business goals.

• Explain AI Tool Usage: Be prepared to discuss how you leveraged AI tools in your workflow and the benefits or challenges encountered.

• Tailor to Mycroft: Research Mycroft's product and industry. Frame your experience in terms of security, compliance, and expert user workflows.

• Demonstrate Mentorship: If applicable, include examples of how you have mentored junior designers or contributed to team skill development.

Challenge Preparation:

• Understand the Domain: Familiarize yourself with common security and compliance frameworks (SOC 2, FedRAMP, CMMC, PCI-DSS) and the types of expert-facing workflows involved.

• Practice Workflow Design: Be ready to sketch out or prototype complex, multi-step workflows.

• Focus on Clarity and Trust: Consider how design can build trust and convey complex information clearly in a high-stakes environment.

• Prepare for AI Integration: Think about how AI can be used responsibly and effectively in design problem-solving.

📝 Enhancement Note: The interview process is structured to assess deep design expertise, domain potential, and collaborative ability. The portfolio review is critical, with a strong emphasis on process, information architecture, and the ability to handle complex, expert-facing B2B products.

🛠 Tools & Technology Stack

Primary Tools:

• Design: Figma is the primary design tool. Proficiency is expected, and candidates should be comfortable using its advanced features for system design and collaboration.

• AI Tooling: Candidates are encouraged to use AI tools (e.g., Claude is mentioned, but others are acceptable) as part of their workflow. Expect to discuss your preferred AI tools and how you integrate them into design processes for efficiency and ideation.

• Domain Knowledge: Familiarity with security and compliance frameworks such as SOC 2, FedRAMP, CMMC, and PCI-DSS is a strong plus, and an appetite to learn these is required.

Analytics & Reporting: While not explicitly listed as a requirement for this role, designers are expected to understand how their designs impact user behavior and compliance outcomes. They will likely work with data from analytics platforms to inform design decisions and measure success.

CRM & Automation: Not directly applicable to the designer role, but understanding how the product integrates with customer workflows and potentially CRM systems might be beneficial for context. The core focus is on the user-facing platform for security and compliance management.

📝 Enhancement Note: The explicit mention of Figma and AI tooling highlights the essential technical skills. The emphasis on domain frameworks underscores the specialized nature of the product and the need for designers to engage with technical subject matter.

👥 Team Culture & Values

Operations Values:

• Rigor and Speed: The company values individuals who can operate at a high pace while maintaining meticulous attention to detail and quality. This is crucial for a security and compliance product where errors have significant consequences.

• Ownership and Autonomy: Employees are trusted to take ownership of their work, pick important tasks, and deliver without constant supervision. This fosters a culture of accountability and initiative.

• Customer-Centricity: While the product serves experts, the underlying goal is to make compliance accessible and manageable for customers. Design decisions should ultimately serve customer needs and outcomes.

• Continuous Learning: The rapidly evolving nature of AI and security/compliance necessitates a commitment to ongoing learning and adaptation. The company encourages embracing new tools and domain knowledge.

• Collaboration and Mentorship: A strong emphasis on working together, sharing knowledge, and elevating the skills of the entire team, particularly through mentorship.

Collaboration Style:

• Close Cross-functional Integration: Designers work "in lockstep" with Engineering and FDEs, indicating a highly integrated and collaborative approach. This isn't about siloed design work; it's about deep partnership.

• Direct Communication: Expect open and direct communication, with designers expected to negotiate scope directly with engineers and articulate their decisions clearly.

• Feedback Culture: Mentorship and critique are central to raising the team's bar, suggesting an environment where constructive feedback is regularly exchanged.

• Shared Domain Expertise: The immersion into FDE work means designers will share a developing understanding of the security and compliance domain with customer-facing operations roles.

📝 Enhancement Note: The core values revolve around a balance of speed and precision, individual ownership, and collaborative growth. The emphasis on cross-functional integration, particularly with engineering and operational roles (FDEs), is a key characteristic of the team's working style.

⚡ Challenges & Growth Opportunities

Challenges:

• Complexity of Domain: Navigating the intricate world of security and compliance frameworks, controls, and risk management requires significant learning and adaptation.

• Balancing Speed and Rigor: The company's rapid growth and fast-paced environment demand quick iteration, which can be challenging to balance with the meticulousness required for security and compliance design.

• Expert-Facing Design: Designing for highly technical users requires a deep understanding of their workflows, mental models, and information needs, which can be more demanding than designing for a general audience.

• AI Integration Responsibility: Effectively leveraging AI tools while maintaining full accountability for design quality and defensibility presents a unique challenge.

• Scaling Design Systems: Evolving a design system to support rapid product expansion while maintaining consistency and quality requires strategic thinking and disciplined execution.

Learning & Development Opportunities:

• Deep Domain Expertise: Gain unparalleled knowledge in the security and compliance industry, a high-demand specialization.

• AI Design Workflow Mastery: Become highly proficient in integrating AI tools into sophisticated design processes.

• Design Leadership: Develop leadership skills through mentoring a junior designer and contributing to the overall design strategy and standards of a growing company.

• Product Strategy Influence: Play a key role in shaping the product roadmap and user experience of an innovative AI-native platform.

• Startup Environment Experience: Gain valuable experience in a fast-paced, high-growth startup, learning to navigate ambiguity and drive impact.

📝 Enhancement Note: The challenges are directly tied to the specialized nature of the product and the company's growth stage. The learning opportunities are significant, offering specialized domain expertise, advanced AI tool proficiency, and leadership development.

💡 Interview Preparation

Strategy Questions:

• "Describe a time you owned and evolved a design system. What were the biggest challenges, and how did you overcome them?" (Focus on your process, decision-making, and impact.)

• "Walk us through a complex B2B workflow you designed. How did you approach information architecture, state logic, and ensure clarity for expert users?" (Be prepared to show diagrams and explain your rationale.)

• "How do you balance the need for speed and iteration with the rigor required for critical domains like security and compliance?" (Highlight your ability to be both fast and meticulous.)

• "Tell us about a time you worked closely with engineers to implement a complex design. How did you ensure design-to-build fidelity, and how did you handle trade-offs?" (Showcase your collaborative and negotiation skills.)

• "How do you leverage AI tools in your design process? Provide an example of how AI helped you solve a specific design problem or improve efficiency." (Be specific about tools and outcomes.) Company & Culture Questions:

• "What interests you about Mycroft's mission in AI-native security and compliance?" (Demonstrate genuine interest and understanding of the domain.)

• "How do you approach mentoring junior designers, and what is your philosophy on raising a team's design bar?" (Highlight your leadership potential and collaborative spirit.)

• "Describe your ideal working relationship with engineering and product leadership in a hybrid environment." (Show your adaptability and communication style.)

• "What does 'ownership' mean to you in a product design role at an early-stage company?" (Reflect on accountability and initiative.) Portfolio Presentation Strategy:

• Structure for Impact: Organize your portfolio around key projects that best showcase your experience with complex B2B workflows, design systems, and expert-facing interfaces.

• Tell a Story: For each case study, clearly articulate the problem, your role, the process, the solutions you designed, and the outcomes. Focus on the "why" behind your decisions.

• Show the "Underneath": Prioritize demonstrating your understanding of information architecture, state logic, and system design. Use diagrams, flowcharts, and detailed explanations.

• Highlight Design System Work: Dedicate a section to your experience with design systems, showing examples of components, patterns, and your contribution to their evolution.

• Discuss AI Integration: Be prepared to talk about how you used AI tools within your projects, focusing on efficiency gains, new creative possibilities, or problem-solving.

• Be Ready for Deep Dives: Anticipate detailed questions about your design decisions, trade-offs, and collaboration with engineers.

📝 Enhancement Note: Interview preparation should focus on demonstrating deep expertise in complex B2B design, a strong understanding of design systems, and the ability to integrate AI tools responsibly. The emphasis on domain immersion and collaboration is key.

📌 Application Steps

To apply for this Senior Product Designer position:

• Submit your application through the provided link on Ashby.

• Curate Your Portfolio: Select 2-3 of your most relevant projects that showcase complex B2B/expert-facing workflows, design system contributions, and your approach to information architecture and state logic. Tailor the presentation to highlight how your skills align with Mycroft's needs in security and compliance.

• Optimize Your Resume: Ensure your resume clearly articulates your 6+ years of experience, specifically mentioning work on complex, data-heavy, or regulated B2B products. Highlight achievements related to design system development and mentorship.

• Prepare Your Presentation: Practice walking through your portfolio case studies, focusing on your process, decision-making, collaboration with engineers, and any use of AI tools. Be ready to discuss the challenges and outcomes of each project.

• Research Mycroft: Understand Mycroft's AI-native security and compliance platform, its mission, and its target market. Be prepared to discuss why this specific domain interests you and how your design skills can contribute to their success.

⚠️ 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.

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