Senior Product Designer

📍 Job Overview

Job Title: Senior Product Designer

Company: Daloopa

Location: Toronto, Canada

Job Type: Full-Time, Salaried

Category: Product Design, UX/UI Design

Date Posted: July 24, 2026

Experience Level: 5-10 Years

Remote Status: Remote OK

🚀 Role Summary

• Lead end-to-end product design for Daloopa's Hub and DiamondGate platforms, focusing on complex B2B SaaS workflows and data-dense domains.

• Drive strategic product vision and roadmap definition through strong collaboration with Product Management and Engineering teams.

• Design intuitive information architecture and interaction patterns for AI-assisted workflows, including discovery, analysis, and cross-surface handoffs.

• Champion user-centered design methodologies and contribute to Daloopa's evolving design system with reusable patterns.

📝 Enhancement Note: This role is explicitly for a Senior Product Designer, requiring a strong portfolio in B2B/enterprise SaaS and data-dense domains. The emphasis on "systems rather than screens" and "clarity and error prevention at scale" indicates a need for a designer who can handle intricate data structures and backend configurations, not just front-end UI. The mention of AI agents, LLMs, and specialized tools like Cursor suggests a forward-thinking design approach.

📈 Primary Responsibilities

• Own the complete design lifecycle for critical product areas within Hub and DiamondGate, from initial problem framing and user research to final shipped experience.

• Collaborate closely with Product Managers and Engineering squads to shape product roadmaps, define strategic product vision, and ensure design decisions are evidence-based.

• Translate complex business goals, deep customer insights, and technical constraints into seamless and simple user experiences, even when dealing with intricate underlying data.

• Architect information systems for dense financial and configuration data, ensuring navigability and accessibility rather than merely hiding complexity.

• Design innovative interaction patterns for AI-assisted workflows, including how users discover and trigger AI analyses, command-based search functionalities, and smooth handoffs across web, Excel, and AI agent interfaces.

• Conduct strategic user research with institutional investors and internal stakeholders, translating findings directly into actionable product direction and design improvements.

• Establish and maintain high UX and visual quality standards across assigned product areas, actively contributing to Daloopa's overarching design system and reusable pattern library.

• Utilize rapid prototyping to efficiently validate 0-to-1 concepts and user hypotheses, significantly de-risking engineering investments.

• Manage multiple concurrent projects within a single product team, demonstrating strong organizational and prioritization skills.

• Navigate ambiguity effectively, bringing clarity to both problem definitions and solution spaces for complex product challenges.

📝 Enhancement Note: The responsibilities highlight a need for a designer who can operate autonomously, drive product strategy from a design perspective, and handle complex technical and data challenges. The emphasis on end-to-end ownership and strategic research suggests a senior-level individual contributor role with significant impact.

🎓 Skills & Qualifications

Education: While no specific degree is listed, a strong portfolio and relevant experience are prioritized. Candidates with degrees in Design, HCI, Computer Science, or related fields may have a foundational advantage.

Experience: 4-6+ years of dedicated product design experience, with a substantial portion focused on B2B or enterprise SaaS environments.

Required Skills:

• Proven experience in end-to-end product design, from concept to launch.

• Strong portfolio showcasing information architecture and problem-solving skills in data-dense domains (e.g., fintech, analytics, developer tools, admin platforms).

• Expertise in designing complex workflows and shipping high-quality, functional user experiences beyond just visual aesthetics.

• Experience designing configuration, settings, or administrative interfaces where error prevention and scalability are paramount.

• Strategic thinking capabilities, with the ability to connect design decisions directly to business objectives.

• Proficiency in user-centered design methodologies and design thinking principles.

• Excellent communication and collaboration skills, with the ability to articulate rationale and work effectively across diverse teams.

• Fluency in Figma and modern prototyping workflows.

• Experience with AI-assisted design and coding tools (e.g., Cursor, Claude Code, Codex) for building functional prototypes.

• Aptitude for thinking in systems rather than just individual screens.

• Demonstrated ability to handle and derive energy from dense, structured data. Preferred Skills:

• Domain exposure to financial services, capital markets, or tools specifically built for financial analysts.

• Experience designing for AI agents, LLM-powered products, or command-based interfaces.

• Experience designing across multiple connected surfaces, such as web applications, plugins/add-ins, and agent interfaces.

• Contribution to or deep understanding of design systems and reusable pattern libraries.

📝 Enhancement Note: The requirements emphasize a specific type of designer: one who thrives on complexity, data, and system-level thinking, particularly within B2B SaaS. The explicit mention of AI tools and cross-surface design points to a candidate who is forward-thinking and adaptable to emerging technologies and user interaction paradigms.

📊 Process & Systems Portfolio Requirements

Portfolio Essentials:

• Showcase at least one project where dense, complex data was transformed into a navigable and user-friendly experience.

• Include a case study demonstrating the design of a system that addresses both customer-facing and administrative aspects of a feature.

• Highlight any projects where AI-assisted prototyping tools were utilized to build functional prototypes, ideally with demonstrable outcomes.

• Projects should clearly articulate the problem, your design process, the trade-offs considered, and the impact of your solutions. Process Documentation:

• Your portfolio should implicitly demonstrate your understanding of user research methodologies, information architecture principles, interaction design, and visual design.

• Evidence of iterative design processes, including rapid prototyping and user testing, is highly valued.

• Examples of how you've collaborated with Product Managers and Engineers to shape product direction and ensure successful implementation.

📝 Enhancement Note: The application instructions strongly suggest that the portfolio is the primary evaluation tool. Candidates are expected to proactively demonstrate their ability to handle complexity, system design, and leverage cutting-edge tools, rather than waiting to be asked.

💵 Compensation & Benefits

Salary Range: $173,000 - $190,000 CAD annualized. Candidates who fully meet the role's requirements will be placed at the top of this range.

Benefits:

• Equity options, reflecting a stake in the company's growth and success.

• Comprehensive benefits package, details of which would be provided during the hiring process.

Working Hours: Standard full-time hours are assumed (approximately 40 hours per week), with flexibility often associated with remote roles.

📝 Enhancement Note: The salary range is competitive for a senior-level design role in Toronto, Canada. The inclusion of equity further enhances the compensation package, signaling a growth-stage company focused on retaining key talent. Research into Toronto's cost of living indicates this range is appropriate for senior roles, particularly in the tech sector.

🎯 Team & Company Context

🏢 Company Culture

Industry: Technology, specifically focused on financial data and AI-powered research tools for institutional investors. This places Daloopa at the intersection of FinTech and AI.

Company Size: While not explicitly stated, the mention of "engineering squad" and a "product team" alongside PMs and designers suggests a growing, potentially mid-stage startup or a well-funded early-stage company.

Founded: Information not provided, but the focus on AI and advanced tooling implies a modern tech company.

Team Structure:

• The Senior Product Designer will be embedded within a product team, consisting of a Product Manager and an engineering squad.

• This structure promotes close, agile collaboration and direct impact on product development.

• The role requires cross-functional partnership not only within the immediate product team but also with other design system contributors and potentially internal tooling stakeholders. Methodology:

• Data-driven decision-making, with a strong emphasis on user research and evidence-based design.

• Agile product development, likely involving iterative cycles of design, development, and testing.

• A systems-thinking approach to problem-solving, prioritizing scalable and interconnected solutions.

• Emphasis on quality and error prevention, especially critical for financial data and internal tooling.

Company Website: daloopa.com

📝 Enhancement Note: Daloopa operates in a sophisticated niche, serving institutional research analysts. This implies a need for a culture that values deep domain expertise, precision, and a commitment to solving complex problems for a demanding user base. The focus on AI suggests a culture of innovation and forward-thinking.

📈 Career & Growth Analysis

Operations Career Level: This is a Senior Product Designer role, indicating a position of significant individual contribution and influence. It's a step beyond mid-level, requiring a proven track record of leading complex projects and driving product strategy.

Reporting Structure: The designer will likely report to a Head of Design, Design Lead, or a Senior Product Manager, depending on the specific organizational structure. They will work within a product team structure.

Operations Impact: The role has a direct and substantial impact on Daloopa's core products (Hub and DiamondGate). Success means fundamentally shaping how institutional analysts conduct research and interact with data, directly influencing user adoption, satisfaction, and the company's competitive edge. The success metrics mentioned (e.g., Hub becoming the analyst's primary tool) highlight this significant operational impact.

Growth Opportunities:

• Specialization: Deepen expertise in FinTech design, AI-driven product experiences, and complex data visualization/information architecture.

• Leadership: Potential to become a Design Lead for a product area, mentor junior designers, and influence the broader design strategy and system at Daloopa.

• Impact: Contribute to a rapidly growing product suite in a high-value market, with the opportunity to shape user experiences that directly drive business outcomes.

• Skill Expansion: Gain hands-on experience with cutting-edge AI design tools and the practical application of LLMs in enterprise software.

📝 Enhancement Note: This senior role offers significant growth potential for a designer who excels in complex, data-intensive B2B environments. The opportunity to influence product direction and contribute to a growing design system makes it attractive for those seeking to make a substantial impact.

🌐 Work Environment

Office Type: While the job is listed as "Remote OK" and located in Toronto, Canada, the company may have a physical office. However, the emphasis is on remote work capability.

Office Location(s): Toronto, Ontario, Canada. The remote nature means candidates across Canada may be considered, provided they can work within the specified time zones.

Workspace Context:

• A remote-first or hybrid work environment, emphasizing asynchronous communication and digital collaboration tools.

• Expectation of autonomy and self-direction in managing workload and design processes.

• Access to modern design and collaboration software, including Figma, prototyping tools, and potentially AI-assisted design platforms.

• Collaboration will be primarily digital, involving video calls, shared documents, and project management tools.

Work Schedule: Standard full-time professional hours are expected. While remote work often implies some flexibility, the need to collaborate with PMs and engineering squads within the same time zone (America/Toronto) is crucial. A 40-hour work week is the baseline.

📝 Enhancement Note: The remote nature of the role suggests a focus on asynchronous communication and digital collaboration. Candidates should be comfortable managing their work independently and be proficient with remote collaboration tools.

📄 Application & Portfolio Review Process

Interview Process:

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

• Portfolio Presentation & Deep Dive: Candidates will likely present key projects from their portfolio, focusing on complex data challenges, system design, and AI integration. This will involve discussing their process, rationale, and impact.

• Cross-Functional Interviews: Meetings with Product Management and Engineering stakeholders to assess collaboration style, strategic thinking, and technical understanding.

• Design Challenge (Potential): A take-home assignment or a live design exercise may be given to evaluate specific skills, problem-solving abilities, and approach to ambiguity.

• Final Round: Discussions with design leadership or senior stakeholders to assess cultural fit and overall candidacy.

Portfolio Review Tips:

• Highlight Complexity: Showcase projects that clearly demonstrate your ability to design for data-dense environments and complex workflows. Explicitly call out the challenges related to information architecture and system design.

• Quantify Impact: Whenever possible, include metrics or qualitative feedback to demonstrate the success and impact of your design solutions.

• Showcase Process: Detail your design process, including user research, ideation, prototyping, iteration, and collaboration with engineering. Explain why you made certain decisions.

• AI & Systems Focus: If you have relevant experience, prominently feature projects involving AI-assisted design, LLMs, or designing interconnected systems across multiple platforms.

• Clarity is Key: Ensure your portfolio is well-organized, easy to navigate, and clearly articulates your contributions and the outcomes.

Challenge Preparation:

• Understand the Domain: Familiarize yourself with financial research workflows, institutional analysis, and the challenges faced by research analysts.

• Think Systemically: Practice approaching design problems from a systems perspective, considering data flow, dependencies, and error handling at scale.

• AI Integration: Be ready to discuss how AI can enhance or change existing workflows and how you would design for such integrations.

• Ambiguity Navigation: Prepare to discuss how you tackle ambiguous problems and bring clarity to complex situations.

📝 Enhancement Note: The emphasis on the portfolio and specific application instructions suggests that candidates should tailor their application materials to directly address the company's stated needs for handling complex data, AI integration, and system-level design.

🛠 Tools & Technology Stack

Primary Tools:

• Figma: Essential for UI design, prototyping, and collaboration.

• Prototyping Tools: Proficiency in modern prototyping workflows, likely integrated with Figma or standalone tools for high-fidelity simulations.

• AI-Assisted Design & Coding Tools: Experience with tools like Cursor, Claude Code, or Codex for building functional prototypes is a significant advantage.

Analytics & Reporting:

• While not explicitly mentioned for designers, understanding how to leverage product analytics (e.g., Amplitude, Mixpanel) to inform design decisions and measure impact would be beneficial. CRM & Automation:

• Not directly applicable to the designer's core tools, but awareness of how design impacts CRM and automation workflows within enterprise SaaS is valuable.

📝 Enhancement Note: The explicit mention of AI-assisted design and coding tools is a key differentiator for this role, indicating Daloopa's commitment to leveraging advanced technology in its design process.

👥 Team Culture & Values

Operations Values:

• Data-Driven: Decisions are backed by user research, data analysis, and strategic insights.

• Quality & Precision: A high bar for UX, visual design, and error prevention, especially critical for financial data.

• Systemic Thinking: Prioritizing interconnected solutions and scalable architecture over isolated features.

• Innovation: Embracing new technologies like AI to enhance user workflows and product capabilities.

• Collaboration: Working effectively across product, engineering, and design disciplines to achieve shared goals.

Collaboration Style:

• Highly collaborative, integrated within product teams (PM, Eng).

• Emphasis on clear communication, rationale-driven decision-making, and constructive feedback.

• Likely a mix of synchronous (meetings, calls) and asynchronous (Slack, documentation) communication.

📝 Enhancement Note: The company values suggest a culture that appreciates deep thinking, technical acumen, and a proactive, problem-solving mindset, fitting for a role focused on complex enterprise software.

⚡ Challenges & Growth Opportunities

Challenges:

• Designing for Complexity: Translating dense, structured financial data and intricate configuration options into intuitive user experiences.

• AI Integration: Seamlessly integrating AI-powered features and agent interactions into existing analyst workflows without causing disruption.

• Balancing Customer & Internal Tools: Designing for both the customer-facing Hub platform and the internal DiamondGate provisioning system, ensuring consistency and efficiency.

• Navigating Ambiguity: Tackling new product areas and evolving AI capabilities where clear requirements may not yet exist.

• Setting the Bar: Establishing and maintaining high UX and visual quality standards across multiple product areas and contributing to a growing design system.

Learning & Development Opportunities:

• Deep Domain Expertise: Gaining in-depth knowledge of financial markets, institutional research, and analyst workflows.

• Cutting-Edge AI Design: Hands-on experience designing for AI agents, LLMs, and AI-assisted prototyping.

• System Design Mastery: Developing advanced skills in information architecture and designing complex, interconnected systems.

• Influence and Impact: Opportunity to significantly shape core product offerings and influence the company's design direction.

📝 Enhancement Note: The challenges are directly tied to the unique nature of Daloopa's product and target market, offering rich opportunities for professional growth and skill development for the right candidate.

💡 Interview Preparation

Strategy Questions:

• "Describe a time you designed for a data-dense domain. What were the key challenges, and how did you approach information architecture?"

• "How would you design the interaction for an AI agent that helps research analysts discover company information and trigger financial models?"

• "Walk us through your process for designing a complex configuration or admin interface where error prevention is critical."

• "How do you balance the needs of customer-facing features with internal tooling requirements?" Company & Culture Questions:

• "What interests you about Daloopa's mission and its focus on institutional research analysts?"

• "How do you approach collaboration with Product Managers and Engineers, especially when there are differing opinions?"

• "Describe your experience contributing to or working with a design system. What makes a design system successful?"

• "How do you measure the success of your design solutions beyond visual appeal?" Portfolio Presentation Strategy:

• Structure Your Narrative: For each project, clearly articulate the problem statement, your role, the constraints, your design process (research, ideation, prototyping, testing), key decisions, and the outcome/impact.

• Focus on "Why": Be prepared to explain the rationale behind your design choices, especially concerning information hierarchy, interaction patterns, and data organization.

• Highlight AI/Systemic Work: Dedicate specific time to showcase projects that demonstrate your ability to design for complex systems or integrate AI capabilities, using the requested portfolio elements.

• Be Ready for Technical Questions: Given the mention of AI coding tools, be prepared for discussions about technical feasibility or how you've leveraged technical constraints in your design.

📝 Enhancement Note: Candidates should prepare to articulate their experience with complex data, AI, and system design. The interview process will likely focus on validating these specific skill sets through portfolio review and targeted questions.

📌 Application Steps

To apply for this Senior Product Designer position:

• Submit your application through the provided link on rippling.com.

• Curate Your Portfolio: Ensure your portfolio prominently features projects that showcase your ability to design for dense data, complex workflows, and AI-integrated experiences, aligning with the "Apply" section's specific requests.

• Tailor Your Resume: Highlight your B2B/enterprise SaaS experience, years of relevant product design work, and specific skills in Figma, prototyping, and AI-assisted tools. Quantify achievements where possible.

• Prepare Your Presentation: Practice walking through your portfolio case studies, focusing on articulating your process, decision-making rationale, and the impact of your designs, especially for complex data and system-oriented projects.

• Research Daloopa: Understand Daloopa's mission, target audience (institutional research analysts), and the products (Hub, DiamondGate) to demonstrate genuine interest and cultural alignment.

⚠️ 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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