Senior Product Designer, Proposals

📍 Job Overview

Job Title: Senior Product Designer, Proposals

Company: Jobgether (Partner Company)

Location: Canada

Job Type: Full-time

Category: Product Design / GTM Operations Support

Date Posted: August 05, 2026

Experience Level: Mid-Senior Level (4+ years)

Remote Status: Fully Remote

🚀 Role Summary

• Lead end-to-end product design strategy and execution for the Proposals product area, focusing on customer success and growth.

• Drive product innovation by translating complex problems into intuitive, scalable, and visually polished user experiences within a fast-paced SaaS environment.

• Collaborate closely with product managers, engineers, and cross-functional stakeholders to define solutions, conduct user research, and deliver impactful designs.

• Apply strategic thinking to product decisions, balancing user needs, business objectives, and technical feasibility for effective Go-To-Market (GTM) support.

• Integrate AI tools into the design workflow to enhance ideation, prototyping, and research, contributing to efficient and high-quality outcomes.

📝 Enhancement Note: While this role is primarily a Product Designer position, the focus on "Proposals" and supporting "customer success" and "business growth" within a SaaS context indicates a strong alignment with GTM operations. The designer will be instrumental in creating tools and workflows that directly impact sales enablement, proposal generation efficiency, and ultimately, revenue. Therefore, this enhancement will frame certain aspects through a GTM/Revenue Operations lens where applicable.

📈 Primary Responsibilities

• Own the complete product design lifecycle, from initial discovery and user research through ideation, prototyping, rigorous usability testing, and final delivery of design assets.

• Partner closely with product managers, engineers, and cross-functional stakeholders to define product requirements, identify opportunities, and drive continuous product improvements that support GTM strategies.

• Conduct comprehensive UX research, including user interviews, surveys, and usability testing, to uncover unmet customer needs and translate insights into actionable design solutions that enhance proposal generation and sales processes.

• Create intuitive, scalable, and visually polished user interfaces and experiences that align with user expectations and contribute to achieving key business objectives related to sales conversion and customer acquisition.

• Apply strategic thinking to product decisions, effectively balancing customer impact, development effort, and delivery timelines to ensure timely release of features that support sales enablement and proposal efficiency.

• Advocate for users by ensuring customer needs and pain points are central to all product decisions, particularly those affecting the sales and proposal generation workflows.

• Contribute to a strong design team culture through active participation in design critiques, collaborative workshops, retrospectives, and cross-team initiatives.

• Collaborate with other designers to share knowledge, refine design processes, and elevate the overall quality and consistency of the product's design language.

• Integrate AI tools strategically into the design workflow to accelerate ideation, prototyping, and research phases, thereby improving efficiency and enabling higher-quality design outcomes for GTM tools.

📝 Enhancement Note: The responsibilities listed align directly with a Senior Product Designer's remit. The emphasis on "Proposals," "customer success," and "business impact" suggests a product that directly supports sales operations and GTM efforts. The inclusion of AI tools integration is a forward-thinking requirement that speaks to modern design practices and efficiency gains.

🎓 Skills & Qualifications

Education: Bachelor's degree in Design, Human-Computer Interaction, or a related field, or equivalent practical experience.

Experience: 4+ years of experience supporting full product design lifecycles within SaaS, B2B, or technology environments, with a demonstrable track record of designing and launching successful products or features.

Required Skills:

• Strong ability to break down complex problems into intuitive, engaging, and user-friendly experiences, particularly for business process tools.

• Proficient in user research methodologies, including qualitative and quantitative approaches, and adept at translating research findings into practical, actionable design solutions.

• Strong visual design skills with a keen eye for detail, typography, and layout, ensuring high-quality execution and adherence to design principles.

• Excellent communication and presentation skills, with a proven ability to articulate design decisions clearly and persuasively to influence stakeholders across product, engineering, and business teams.

• Experience collaborating closely with product managers, engineers, and customer-facing teams (e.g., Sales, Customer Success) to ensure alignment and successful product delivery.

• Comfort and experience using AI tools throughout the design process to enhance efficiency, creativity, and output quality.

• A growth mindset with a continuous desire to improve workflows, tools, and design practices, fostering a culture of learning and adaptation. Preferred Skills:

• Experience with construction technology, CRM platforms (e.g., Salesforce, HubSpot), or related business software solutions.

• Prior experience working in fast-paced startup environments, demonstrating adaptability and resourcefulness.

• Familiarity with established design systems and proficiency in modern design tools such as Figma.

📝 Enhancement Note: The experience requirement is clearly stated. The preferred skills, particularly CRM and construction technology, hint at the specific industry or user base the "Proposals" product serves, which is valuable context for a designer. The emphasis on AI tools and a growth mindset are key indicators of a modern, agile design team.

📊 Process & Systems Portfolio Requirements

Portfolio Essentials:

• A comprehensive portfolio is required, showcasing a range of product design projects that demonstrate your ability to handle the full design lifecycle.

• Projects should highlight your strategic thinking, problem-solving skills, and ability to create intuitive user experiences for business-critical applications.

• Include case studies that detail your process, from initial problem definition and user research to ideation, prototyping, testing, and final design solutions.

• Showcase your visual design capabilities and attention to detail in your presented work.

• Demonstrate experience with B2B or SaaS products, ideally those that support complex workflows or business processes. Process Documentation:

• Portfolio case studies should clearly articulate the design process followed, including any user research conducted, problem definition, ideation phases, and iteration based on feedback.

• Highlight how you translated user needs and business requirements into tangible design outputs, such as wireframes, user flows, interactive prototypes, and high-fidelity mockups.

• Include examples of how you collaborated with cross-functional teams (Product, Engineering) and incorporated their input into your design solutions.

• If applicable, demonstrate how you leveraged or integrated AI tools within your design workflow to achieve specific project goals or improve efficiency.

📝 Enhancement Note: A strong portfolio is crucial for design roles. The emphasis here is on demonstrating the process and strategic thinking behind the designs, not just the final visuals. For a role supporting "Proposals," showcasing projects that improved efficiency, reduced complexity, or enhanced user adoption in business workflows would be highly advantageous.

💵 Compensation & Benefits

Salary Range: Competitive compensation based on market benchmarks, experience, and demonstrated impact. As this role is based in Canada, salary will be benchmarked against Canadian market rates for Senior Product Designers in the SaaS/Tech sector. A typical range for a Senior Product Designer in Canada with 4+ years of experience could fall between CAD $90,000 - CAD $130,000 annually, depending on specific location within Canada and the depth of relevant experience.

Benefits:

• Remote-first work environment with flexible working arrangements.

• Competitive compensation package, reflecting market benchmarks and individual impact.

• Employer-paid extended healthcare and dental benefits for Canadian employees.

• Retirement savings support through RRSP matching programs.

• Generous paid time off, including:

  • Mandatory paid time off during the first week of employment.
  • Monthly company-wide Friday wellness days.
  • Holiday shutdown between Christmas and New Year.
  • Flexible vacation policy.

• Generous parental leave benefits.

• Annual company retreat and team-building experiences.

• Learning and development opportunities to support career growth and skill enhancement.

• Home office setup stipend to ensure a comfortable and productive remote workspace.

• Internet and phone allowance to cover essential connectivity costs.

• Weekly pay schedule for consistent financial management.

• Opportunity to work with a collaborative team focused on innovation and customer impact.

Working Hours: Standard full-time hours, typically around 40 hours per week, with flexibility offered given the remote-first nature of the role. The emphasis is on results and impact rather than strict adherence to a 9-to-5 schedule.

📝 Enhancement Note: Salary range is estimated based on typical Canadian market data for a Senior Product Designer. The benefits package is comprehensive, with a strong emphasis on work-life balance and employee well-being, which is attractive for remote roles.

🎯 Team & Company Context

🏢 Company Culture

Industry: Technology / SaaS (Software as a Service), with a potential focus on construction technology or business process automation.

Company Size: Not explicitly stated, but the mention of "fast-paced startup environments" as an advantage and "collaborative team focused on innovation" suggests a dynamic, potentially growing company, likely in the small to medium-sized enterprise (SME) range or a well-funded startup.

Founded: The company is implied to be established enough to offer robust benefits and an annual retreat, but also agile enough to embrace AI and startup culture.

Team Structure:

• The design team likely comprises individuals with diverse specializations, including product design, UX research, and potentially UI design.

• This Senior Product Designer will report into a Design Lead or Head of Product, working within a cross-functional product team that includes Product Managers and Engineers.

• Collaboration is highly emphasized, with a focus on cross-functional partnerships to ensure integrated product development and GTM success. Methodology:

• Data-driven decision-making is core, leveraging user research, analytics, and feedback to inform design strategy.

• Agile methodologies are likely employed for product development, enabling rapid iteration and response to market needs.

• A strong emphasis on user-centered design principles ensures that customer needs are paramount.

• The integration of AI tools suggests a forward-thinking approach to design and operational efficiency.

Company Website: https://jobgether.com/

📝 Enhancement Note: The company culture is presented as innovative, collaborative, and user-centric, with a strong emphasis on modern practices like AI integration. The "Proposals" product area suggests a focus on B2B solutions that streamline business processes, aligning with GTM and sales enablement functions.

📈 Career & Growth Analysis

Operations Career Level: This is a Senior Product Designer role, indicating a level of expertise and autonomy. The "Proposals" focus suggests an opportunity to become a subject matter expert in a critical GTM-related product area, influencing sales efficiency and revenue generation.

Reporting Structure: The Senior Product Designer will report to a Design Manager or Head of Product and will work collaboratively within a dedicated product team. This structure allows for mentorship and guidance while providing significant ownership.

Operations Impact: The work directly impacts the sales process and customer engagement through the Proposals product. By improving the design of proposal generation tools, this role can directly influence sales cycle length, proposal win rates, and overall revenue growth, making it a key contributor to GTM operations success.

Growth Opportunities:

• Specialization: Develop deep expertise in designing for complex B2B workflows, particularly in sales enablement and proposal generation.

• Leadership: Potential to mentor junior designers, lead design initiatives within the Proposals product area, or transition into a Design Lead role.

• Skill Development: Opportunity to become a leader in integrating AI tools into design processes, staying at the forefront of industry innovation.

• Cross-functional Advancement: Gain a comprehensive understanding of product management, engineering, and GTM strategies, opening doors to product leadership roles.

📝 Enhancement Note: The career growth potential is significant, especially for a designer interested in the business impact of their work. The role offers a clear path to becoming a specialist in a crucial GTM area, with opportunities for leadership and skill expansion in emerging technologies.

🌐 Work Environment

Office Type: Remote-first, offering maximum flexibility and autonomy.

Office Location(s): Primarily remote within Canada, allowing candidates to work from their preferred location.

Workspace Context:

• A fully remote setup means the designer will be responsible for their home office environment, supported by a stipend.

• Collaboration will primarily occur through digital tools, emphasizing strong communication and asynchronous work practices.

• The team culture encourages interaction and knowledge sharing despite the remote setup, likely through regular virtual meetings, Slack channels, and collaborative design sessions.

• Access to modern design and collaboration tools is expected to facilitate effective remote work.

Work Schedule: Flexible, with a focus on delivering results within a standard full-time workload. This allows for better work-life integration, which is beneficial for deep work and creative problem-solving.

📝 Enhancement Note: The remote-first environment is a significant perk, but it requires self-discipline and strong communication skills. The company's commitment to providing stipends and allowances supports a productive remote workspace.

📄 Application & Portfolio Review Process

Interview Process:

• Initial Screening: Application review via Jobgether's AI-powered system, followed by a potential recruiter screen.

• Design Challenge/Portfolio Review: A critical stage involving a review of your portfolio, likely with a focus on relevant case studies. You may be asked to present specific projects and discuss your design process, strategic thinking, and problem-solving approach.

• Team Interviews: Meetings with Product Managers, Engineers, and potentially other designers to assess technical skills, collaborative abilities, and cultural fit.

• Final Interview: Typically with a hiring manager or senior leader to discuss overall fit, career aspirations, and potential impact.

Portfolio Review Tips:

• Curate Strategically: Select 2-3 case studies that best demonstrate your experience with B2B SaaS products, full-cycle design, user research, and problem-solving. If possible, include projects related to business process optimization, sales enablement, or proposal generation.

• Showcase Process: Clearly articulate your design process, including how you identified user needs, defined problems, explored solutions, and iterated based on feedback. Use visuals (user flows, wireframes, prototypes) to illustrate your journey.

• Quantify Impact: Whenever possible, include metrics or outcomes that demonstrate the impact of your designs (e.g., improved conversion rates, reduced task completion time, increased user satisfaction). For a "Proposals" role, this could relate to sales cycle acceleration or proposal accuracy.

• Highlight Collaboration: Explain how you partnered with cross-functional teams (Product, Engineering, Sales) and how their input shaped your designs.

• AI Integration: If you have experience using AI tools in your design process, be prepared to discuss how you leveraged them and the benefits they provided.

Challenge Preparation:

• Understand the Product: Research Jobgether and its partner companies to understand their mission, target audience, and the type of B2B SaaS products they offer.

• Prepare for "Proposals" Focus: Think about the common challenges and user needs associated with generating business proposals. Consider features that could improve efficiency, accuracy, customization, and integration with other sales tools.

• Practice Articulating Decisions: Be ready to clearly explain the "why" behind your design choices, linking them back to user needs and business objectives.

📝 Enhancement Note: The application process emphasizes a strong portfolio and the ability to articulate design strategy and impact. Candidates should prepare case studies that highlight their experience with business-critical applications and their understanding of B2B user needs.

🛠 Tools & Technology Stack

Primary Tools:

• Design & Prototyping: Figma is explicitly mentioned as preferred. Proficiency in other industry-standard tools like Sketch, Adobe Creative Suite (Illustrator, Photoshop) is also valuable.

• User Research & Testing: Tools such as UserTesting.com, Maze, Lookback, or even survey platforms like SurveyMonkey or Typeform.

• Collaboration & Project Management: Jira, Confluence, Asana, Trello, Slack, Microsoft Teams.

Analytics & Reporting:

• Understanding of product analytics tools (e.g., Amplitude, Mixpanel, Google Analytics) to inform design decisions and measure impact.

• Experience with data visualization tools or dashboards that present user behavior and product performance metrics. CRM & Automation:

• Familiarity with CRM systems (e.g., Salesforce, HubSpot) is a plus, as the "Proposals" product may integrate with or serve users of these platforms.

• Understanding of workflow automation principles within SaaS products.

📝 Enhancement Note: Proficiency in Figma is a key requirement. The role also benefits from familiarity with CRM systems and analytics tools, underscoring the connection to GTM and sales operations.

👥 Team Culture & Values

Operations Values:

• User-Centricity: A deep commitment to understanding and serving the needs of business users, ensuring that designs are intuitive and valuable.

• Innovation: Embracing new technologies and methodologies, such as AI, to drive product improvement and efficiency.

• Collaboration: Working effectively across teams to achieve shared goals, fostering an environment of mutual respect and open communication.

• Impact-Driven: Focusing on delivering designs that have a measurable positive effect on business outcomes, such as revenue growth and customer success.

• Continuous Improvement: A dedication to refining processes, tools, and skills to achieve higher quality and efficiency in design work.

Collaboration Style:

• Cross-functional Integration: Actively engaging with Product Management, Engineering, Sales, and Customer Success teams to ensure holistic product development and alignment with GTM strategies.

• Feedback Culture: Openness to giving and receiving constructive feedback through design critiques and team retrospectives to foster growth and enhance design quality.

• Knowledge Sharing: A proactive approach to sharing insights, best practices, and learnings within the design team and across the organization.

📝 Enhancement Note: The culture emphasizes innovation, user focus, and tangible business impact, which are crucial for roles supporting GTM operations. The collaborative style is essential for a remote team working on complex products.

⚡ Challenges & Growth Opportunities

Challenges:

• Balancing Diverse Needs: Effectively integrating the needs of various stakeholders (users, sales, engineering, business) into a cohesive design solution for the Proposals product.

• Navigating Ambiguity: Working in a fast-paced environment where requirements may evolve, requiring adaptability and strong problem-solving skills.

• Remote Collaboration: Maintaining strong working relationships and effective communication in a fully remote setting.

• AI Integration: Successfully incorporating AI tools into existing workflows to enhance efficiency without compromising design quality or user experience.

Learning & Development Opportunities:

• Advanced Design Techniques: Deepen expertise in complex B2B UX design, user research methodologies, and creating scalable design systems.

• Industry Trends: Stay ahead of the curve with advancements in AI for design, emerging SaaS technologies, and best practices in GTM product development.

• Leadership Skills: Develop mentorship capabilities and potentially take on lead roles for specific product initiatives or design areas.

• Business Acumen: Gain a deeper understanding of sales processes, revenue operations, and the strategic impact of design on business growth.

📝 Enhancement Note: The challenges presented are typical for senior roles in dynamic tech companies. The growth opportunities are robust, focusing on both technical design skills and broader business and leadership development.

💡 Interview Preparation

Strategy Questions:

• "Describe a complex B2B SaaS problem you solved through design. What was your process, what challenges did you face, and what was the impact?" (Focus on process, problem-solving, and quantifiable results.)

• "How do you approach user research for a product like 'Proposals' that serves a specific business function? What methods would you use, and how would you translate findings into design decisions?" (Demonstrate research methodology and user empathy.)

• "How would you integrate AI tools into the design process for a feature like proposal generation? What are the potential benefits and risks?" (Showcase forward-thinking and practical application of AI.)

• "Describe a time you had to influence stakeholders with differing opinions on a design direction. How did you approach it, and what was the outcome?" (Assess communication, negotiation, and stakeholder management skills.) Company & Culture Questions:

• "Why are you interested in designing for a product area like 'Proposals' within a B2B SaaS company?" (Connect your skills and interests to the role's specific focus.)

• "How do you contribute to a positive and productive team culture, especially in a remote environment?" (Highlight collaboration and communication skills.)

• "What does user-centricity mean to you, and how do you ensure it's prioritized in your design work?" (Assess your understanding of core design principles.) Portfolio Presentation Strategy:

• Structure: Organize your presentation logically, typically starting with an overview of the company/problem, your role, the process, key decisions, and finally, the outcomes and learnings.

• Storytelling: Frame each case study as a narrative, highlighting the problem, your journey to the solution, and the impact achieved.

• Visuals: Use high-quality visuals (wireframes, mockups, prototypes, user flows) to support your explanation. Keep text concise.

• Metrics: Be prepared to discuss any metrics or data that demonstrate the success of your designs. If direct metrics aren't available, discuss how you would measure success or what key performance indicators (KPIs) are relevant.

• AI Integration: If applicable, clearly articulate how AI tools were used in the presented projects and the value they brought.

📝 Enhancement Note: Interview preparation should focus on demonstrating strategic thinking, problem-solving abilities, and a clear understanding of B2B SaaS product design, particularly for business process-oriented tools. The ability to articulate the impact of design is paramount.

📌 Application Steps

To apply for this Senior Product Designer position:

• Submit your application through the Jobgether portal.

• Curate Your Portfolio: Select 2-3 of your strongest B2B SaaS or complex workflow design case studies. Prioritize projects that showcase your end-to-end design process, user research capabilities, strategic problem-solving, and quantifiable impact. If you have experience with proposal generation tools, CRM integrations, or AI in design, highlight these prominently.

• Optimize Your Resume: Ensure your resume clearly outlines your 4+ years of experience in SaaS/B2B product design. Use keywords from the job description (e.g., "Product Design," "User Research," "Figma," "SaaS," "B2B," "AI tools," "Stakeholder Management"). Quantify achievements where possible.

• Prepare Your Presentation: Practice walking through your chosen portfolio case studies. Be ready to articulate your design process, the "why" behind your decisions, how you collaborated with teams, and the outcomes of your work. Prepare to discuss your experience with AI tools.

• Research the Company: Understand Jobgether's mission and the potential partner company's industry (e.g., construction tech, B2B software). This will help you tailor your application and interview responses to their specific context and operational needs.

⚠️ 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.