Director, AI Product Strategy

📍 Job Overview

Job Title: Director, AI Product Strategy

Company: Jobgether (for a partner company)

Location: Canada (Remote for US-based candidates)

Job Type: Full-time

Category: Product Management / AI Strategy / GTM Operations

Date Posted: 2026-09-17

Experience Level: 10+ years

Remote Status: Fully Remote (within the United States)

🚀 Role Summary

• Lead the strategic direction and execution of AI-powered product initiatives, focusing on agentic workflows and large language models (LLMs).

• Drive the end-to-end product lifecycle, from initial discovery and research through to launch and post-launch evaluation, ensuring alignment with business objectives and technological capabilities.

• Act as a senior client advisor, translating complex business challenges into scalable digital and AI solutions, fostering strong stakeholder relationships.

• Collaborate closely with multidisciplinary teams, including Design, Engineering, Program Delivery, and Marketing, to deliver sophisticated digital products and AI experiences.

• Leverage practical, hands-on knowledge of emerging AI technologies to develop and implement real-world applications that transform both consumer experiences and internal operations.

📝 Enhancement Note: While the role is located in Canada, the benefits section explicitly states a "Fully remote position within the United States." This suggests the primary hiring pool or operational base for the role is in the US, but applications from Canada might be considered if they meet specific criteria or if the partner company has a presence there. Clarification on the exact location requirements for Canadian applicants is recommended. This role is categorized under GTM Operations due to its focus on product strategy, market readiness, and driving business outcomes through AI-driven solutions.

📈 Primary Responsibilities

• Architect comprehensive, end-to-end AI agent workflows designed to revolutionize consumer-facing digital experiences and optimize complex internal client operations.

• Take ownership of the entire product lifecycle, encompassing discovery, in-depth research, strategic planning, meticulous requirements gathering, validation, user-centered design, technology delivery, and successful launch.

• Translate intricate business requirements and the evolving landscape of AI capabilities into clear, actionable product strategies, compelling narratives, and quantifiable business outcomes for senior executive stakeholders.

• Forge robust partnerships with Design, Engineering, Program Delivery, Marketing, and Client Partnership teams to define strategic direction, facilitate iterative solution development, and rigorously validate technical feasibility.

• Provide effective leadership to multidisciplinary teams comprising strategy, design, and technology experts, cultivating a collaborative and high-velocity delivery environment.

• Serve as a trusted advisor and recognized subject matter expert during client engagements, applying a strong foundation in agency and consulting principles to address complex product challenges.

• Cultivate deep, collaborative partnerships with senior client stakeholders, adeptly balancing critical business requirements and operational logic with user needs, intrinsic goals, and overall user experience.

• Apply practical, hands-on expertise with AI tools and cutting-edge technologies to conceptualize and develop viable solutions that transition effectively from experimentation and proof-of-concept phases into tangible, real-world implementations.

📝 Enhancement Note: The responsibilities highlight a strong emphasis on client-facing consulting and strategic advisory, typical of roles within digital agencies or consulting firms. The focus on "architecting end-to-end AI agent workflows" and "transforming consumer-facing digital experiences and complex internal client operations" indicates a need for candidates who can bridge strategic vision with practical execution in complex business environments.

🎓 Skills & Qualifications

Education: While no specific degree is listed, a strong academic background in Computer Science, Engineering, Business, or a related field is often implied for such strategic product roles.

Experience: Minimum of 10 years of progressive experience in product management, digital strategy, or consulting, with a significant portion focused on AI and digital product development.

Required Skills:

• Proven track record within a digital agency, consulting firm, or a similarly client-centric organization, demonstrating success in client engagements.

• Deep expertise in product management or product ownership, evidenced by a history of successfully launching large-scale, consumer-facing digital products across web, mobile applications, CMS, or enterprise platforms.

• Practical, applied experience with modern AI technologies, including but not limited to agentic design principles, AI governance frameworks, workflow transformation methodologies, and AI-powered product development lifecycles.

• Demonstrated capability to guide AI concepts from initial experimentation or proof-of-concept stages through to full production, successful launch, and comprehensive post-launch evaluation.

• Solid understanding of the distinctions between deterministic and probabilistic systems, with the ability to design effective products and workflows that leverage these characteristics.

• Hands-on experience or robust working knowledge of cloud computing ecosystems and large language model (LLM) platforms, such as Google Cloud (Vertex AI), Gemini Enterprise Agents, Anthropic Claude, OpenAI, and Microsoft Copilot.

• Exceptional ability to seamlessly integrate strategic thinking with hands-on delivery and effective technical problem-solving.

• Superior communication and storytelling skills, with a proven capacity to articulate sophisticated technical and AI concepts to diverse audiences, including senior executives and non-technical stakeholders.

• Demonstrated leadership experience with multidisciplinary teams, coupled with a strong ability to collaborate effectively across strategy, design, engineering, program delivery, marketing, and client-facing functions.

• Acute business judgment, strong product intuition, advanced problem-solving capabilities, and comfort operating adeptly in ambiguous and rapidly evolving environments. Preferred Skills:

• Experience in defining and executing go-to-market (GTM) strategies for AI-powered products.

• Familiarity with agile methodologies and frameworks for product development and delivery.

• Experience with user research, journey mapping, and usability testing in AI-driven product contexts.

• Knowledge of data privacy regulations and ethical considerations in AI product development.

• Experience with product analytics tools and methodologies for measuring AI product performance.

📝 Enhancement Note: The requirements strongly suggest a candidate with a blend of strategic consulting acumen and deep technical product management expertise, particularly in the AI domain. The emphasis on client-facing experience and the ability to translate complex technical concepts to executive audiences points towards a senior-level role requiring strong business and communication skills alongside technical depth. The mention of specific LLM platforms indicates a need for practical, hands-on experience rather than just theoretical knowledge.

📊 Process & Systems Portfolio Requirements

Portfolio Essentials:

• Showcase a portfolio that demonstrates successful product launches, with a focus on digital products and AI-driven solutions.

• Include case studies detailing the full product lifecycle management, from initial ideation and strategic planning through to development, launch, and post-launch analysis.

• Present examples of how you have translated complex business challenges into tangible product strategies and measurable outcomes, particularly involving AI technologies.

• Highlight your experience in leading multidisciplinary teams and collaborating effectively across different functions (e.g., design, engineering, marketing) to achieve product goals.

• Demonstrate your ability to articulate technical and AI concepts clearly to non-technical stakeholders, supported by examples of presentations or strategic documents. Process Documentation:

• Evidence of defining and documenting product requirements, user stories, and technical specifications for AI-powered products.

• Examples of workflow designs and optimization strategies implemented for AI agentic systems or LLM-based applications.

• Documentation of product strategy frameworks and roadmaps developed for AI product initiatives.

• Records of user validation, A/B testing, or other methods used to iterate on and improve AI product features and user experiences.

📝 Enhancement Note: For a role at this level, a portfolio is crucial. It should not only list past projects but also provide deep dives into the candidate's strategic thinking, problem-solving approach, and execution capabilities, especially concerning AI product development and client engagements. The emphasis is on demonstrating impact and strategic influence.

💵 Compensation & Benefits

Salary Range: $170,000–$200,000 USD per year.

Benefits:

• Fully remote position within the United States.

• Opportunity to work at the forefront of AI, product strategy, design, and technology.

• Exposure to cutting-edge AI tools, agentic workflows, cloud platforms, and LLM ecosystems.

• Chance to lead high-impact digital transformation initiatives for prominent client organizations.

• Collaborative and multidisciplinary working environment fostering innovation and expertise exchange.

• Inclusive workplace culture committed to authentic employee contributions.

• Accessible and barrier-free recruitment and employment processes, with accommodations available as needed.

Working Hours: Assumed to be standard full-time hours (approximately 40 hours per week), with flexibility expected due to the remote nature and client-facing responsibilities.

📝 Enhancement Note: The salary range provided is competitive for a Director-level AI Product Strategy role in the US, especially for a remote position. The benefits highlight the unique opportunity to work with advanced AI technologies and lead significant digital transformation projects, appealing to ambitious professionals in the field. The remote work benefit is specifically tied to the United States, reinforcing the primary operational focus for this role.

🎯 Team & Company Context

🏢 Company Culture

Industry: The partner company operates within the technology sector, likely focusing on digital product development, AI solutions, and strategic consulting services. Jobgether itself is an AI-powered recruitment platform.

Company Size: Not explicitly stated for the partner company, but the role implies a mature organization with established client relationships and multidisciplinary teams capable of handling complex digital transformations. Jobgether's size is not specified but operates as a tech platform.

Founded: The founding date of the partner company is not provided. Jobgether's founding is not specified.

Team Structure:

• The role involves leading multidisciplinary teams, suggesting a matrixed or project-based structure where individuals from strategy, design, engineering, program delivery, and marketing collaborate.

• This Director will likely report to a senior executive within the partner company, such as a VP of Product, Head of AI, or Chief Strategy Officer.

• Close collaboration with client partnership teams is essential for managing senior client stakeholders and understanding their operational needs. Methodology:

• The company likely employs agile methodologies for product development and delivery, emphasizing iterative improvements and rapid prototyping.

• A strong focus on user-centered design and data-driven decision-making is expected, particularly in translating business requirements into effective AI solutions.

• The approach involves a blend of strategic consulting, hands-on technical execution, and client advisory services.

Company Website: https://jobgether.com/how-jobgether-works (for Jobgether's platform)

📝 Enhancement Note: The emphasis on multidisciplinary teams and client advisory suggests a dynamic, project-driven environment common in consulting or digital product studios. The use of AI for matching by Jobgether implies a tech-forward approach to recruitment itself.

📈 Career & Growth Analysis

Operations Career Level: Director, AI Product Strategy. This is a senior leadership role focused on defining and executing the strategy for AI products, influencing product roadmaps, and driving significant business outcomes through technology innovation. It requires a blend of strategic vision, deep technical understanding, and strong leadership capabilities.

Reporting Structure: The Director will likely report to a senior executive within the partner company (e.g., VP of Product, CTO, Head of AI Strategy). They will, in turn, lead and mentor multidisciplinary teams.

Operations Impact: This role has a direct impact on the company's ability to deliver cutting-edge AI solutions to clients, driving revenue growth and market differentiation. The Director's strategic decisions will shape product offerings, client engagements, and the overall success of AI initiatives.

Growth Opportunities:

• Potential to advance into executive leadership roles within AI product management, such as VP of AI Product or Chief Product Officer, focusing on broader product portfolios.

• Opportunities to specialize further in specific AI domains (e.g., Generative AI, Agentic Systems) or take on broader strategic leadership responsibilities.

• Develop expertise in client relationship management and consultative selling at the executive level.

• Mentor and develop junior product managers and strategists, contributing to the growth of the operations team and company.

📝 Enhancement Note: This role offers significant growth potential for individuals looking to lead in the rapidly evolving AI product space. The combination of strategic, technical, and client-facing responsibilities provides a well-rounded development path towards senior leadership.

🌐 Work Environment

Office Type: The role is advertised as fully remote. This implies a distributed workforce where employees work from their own locations.

Office Location(s): The role is stated to be fully remote within the United States. While the listing mentions Canada for the initial posting, the operational requirement for the candidate is US-based remote work.

Workspace Context:

• Candidates will need a dedicated, professional home office setup conducive to productive work and virtual collaboration.

• Access to reliable high-speed internet is essential for seamless participation in video conferences, remote tool usage, and project collaboration.

• The work environment emphasizes autonomy and self-management, requiring strong organizational skills and the ability to work independently.

• Collaboration will primarily occur through digital tools, necessitating proficiency in communication platforms and project management software.

Work Schedule: Standard full-time hours (approx. 40 hours/week) are expected. Given the client-facing nature and remote setting, some flexibility may be required to accommodate different time zones or client needs.

📝 Enhancement Note: The fully remote aspect offers flexibility but requires strong self-discipline and effective digital communication skills. Candidates should be comfortable working without a traditional office environment and managing their own work schedule effectively.

📄 Application & Portfolio Review Process

Interview Process:

• Initial Screening: AI-powered review by Jobgether to assess core qualifications and fit against requirements.

• Hiring Manager/Team Interview: A discussion with the partner company's hiring manager and potentially key team members to delve into strategic thinking, AI expertise, and leadership capabilities. Expect questions on AI product strategy, agentic workflows, LLM applications, and client management.

• Case Study/Presentation: Candidates may be asked to present a case study from their portfolio or a hypothetical scenario demonstrating their approach to a complex AI product challenge, focusing on strategy, execution, and impact.

• Stakeholder Interviews: Interviews with senior stakeholders (internal and potentially client-facing) to assess communication, influence, and advisory skills.

• Final Round: Discussions with executive leadership to confirm strategic alignment and cultural fit.

Portfolio Review Tips:

• Curate your portfolio to prominently feature AI-driven products, agentic workflows, and successful digital transformations.

• For each project, clearly articulate the business problem, your strategic approach, the AI technologies used, your role in leading the multidisciplinary team, and the measurable business outcomes achieved (e.g., ROI, efficiency gains, user adoption).

• Be prepared to walk through your portfolio, explaining your decision-making process and how you navigated challenges.

• Quantify results wherever possible, using metrics that demonstrate impact on revenue, cost savings, or customer satisfaction.

• Tailor your portfolio presentation to highlight experience relevant to client advisory and complex problem-solving. Challenge Preparation:

• Prepare to discuss your hands-on experience with specific LLMs and cloud AI platforms mentioned in the requirements (Google Cloud, Vertex AI, Gemini, Claude, OpenAI, Copilot).

• Be ready to articulate your understanding of deterministic vs. probabilistic systems and how you'd design products around them.

• Practice explaining complex AI concepts and product strategies concisely and persuasively to both technical and non-technical audiences.

• Develop talking points on how you've led multidisciplinary teams through the full product lifecycle, especially in fast-paced, ambiguous environments.

📝 Enhancement Note: The interview process is designed to assess a candidate's strategic depth, technical acumen in AI, leadership potential, and client-facing consulting skills. A well-prepared portfolio and clear articulation of past successes are paramount.

🛠 Tools & Technology Stack

Primary Tools:

• AI Platforms & Ecosystems: Google Cloud (Vertex AI), Gemini Enterprise Agents, Anthropic Claude, OpenAI, Microsoft Copilot.

• Cloud Computing: General familiarity with cloud infrastructure and services is expected.

• Product Management Tools: Jira, Confluence, Asana, Trello, or similar for workflow management, requirements tracking, and documentation.

• Collaboration Tools: Slack, Microsoft Teams, Zoom, Google Meet for communication and virtual meetings.

Analytics & Reporting:

• Experience with product analytics platforms (e.g., Google Analytics, Mixpanel, Amplitude) for tracking user behavior and product performance.

• Familiarity with data visualization tools (e.g., Tableau, Power BI) for reporting on AI product metrics and business outcomes. CRM & Automation:

• While not the primary focus, understanding how AI products integrate with CRM systems (e.g., Salesforce, HubSpot) and impact sales/marketing automation workflows is beneficial.

• Experience with workflow automation tools, particularly those that can leverage AI capabilities.

📝 Enhancement Note: Proficiency with specific AI platforms like Vertex AI, Gemini, Claude, OpenAI, and Copilot is a critical requirement. Candidates should be prepared to discuss their practical application and experience in leveraging these tools for product development.

👥 Team Culture & Values

Operations Values:

• Innovation & Forward-Thinking: A strong drive to explore and implement cutting-edge AI technologies to solve real-world problems.

• Client-Centricity: A commitment to understanding and exceeding client expectations by delivering tailored, high-impact solutions.

• Collaboration & Teamwork: A belief in the power of multidisciplinary teams working together to achieve shared goals.

• Data-Driven Decision Making: Utilizing data and analytics to inform product strategy, measure performance, and drive continuous improvement.

• Agility & Adaptability: Comfort and proficiency in navigating fast-paced, ambiguous environments and adapting to evolving technologies and business needs.

Collaboration Style:

• Cross-functional collaboration is essential, requiring open communication and a willingness to work closely with diverse teams (strategy, design, engineering, delivery, marketing).

• A consultative approach, involving active listening, problem-solving, and strategic partnership with both internal teams and external clients.

• Emphasis on knowledge sharing and continuous learning within the rapidly evolving AI landscape.

• A culture that encourages constructive feedback and iterative development to ensure product excellence.

📝 Enhancement Note: The culture appears to value innovation, client success, and collaborative execution, typical of high-performing consulting or product development firms. Candidates should demonstrate an ability to thrive in such a dynamic and client-focused environment.

⚡ Challenges & Growth Opportunities

Challenges:

• Rapidly Evolving AI Landscape: Staying abreast of the latest advancements in AI, LLMs, and agentic workflows to ensure product strategies remain relevant and competitive.

• Translating Ambiguity into Clarity: Effectively navigating complex client business challenges and technical uncertainties to define clear product roadmaps and actionable strategies.

• Cross-Functional Alignment: Ensuring seamless collaboration and alignment among diverse teams with potentially different priorities and technical understandings.

• Client Expectations Management: Balancing ambitious AI capabilities with realistic client expectations and operational constraints to ensure successful project delivery.

Learning & Development Opportunities:

• Continuous learning opportunities through exposure to diverse AI technologies, platforms, and client projects.

• Potential to attend industry conferences and workshops focused on AI, product management, and digital transformation.

• Opportunities for mentorship from senior leaders within the partner organization, fostering leadership and strategic development.

• Possibility of pursuing certifications in AI, cloud technologies, or advanced product management methodologies.

📝 Enhancement Note: This role presents exciting challenges at the forefront of AI innovation, offering significant opportunities for professional growth and skill development in a dynamic field.

💡 Interview Preparation

Strategy Questions:

• "Describe a time you had to translate a complex business problem into an AI product strategy. What was your approach, and what was the outcome?" (Focus on strategic thinking, problem decomposition, and measurable results).

• "How do you balance the potential of emerging AI technologies with the practical constraints of client operations and existing infrastructure?" (Prepare to discuss risk assessment, phased implementation, and value proposition articulation).

• "Walk us through your process for managing the full lifecycle of a large-scale digital product, with a specific emphasis on AI components." (Highlight your methodology, key decision points, and how you ensure successful delivery). Company & Culture Questions:

• "What interests you most about working at the intersection of AI, product strategy, and client consulting?" (Show genuine enthusiasm for the role's unique blend of responsibilities).

• "How do you foster collaboration among multidisciplinary teams, especially in a remote environment?" (Provide examples of your leadership style and communication strategies).

• "How do you ensure your AI product recommendations align with a client's long-term business objectives and operational capabilities?" (Demonstrate your consultative approach and strategic foresight). Portfolio Presentation Strategy:

• Select 2-3 key projects that best showcase your experience with AI product strategy, agentic workflows, and client advisory.

• For each project, clearly define the business challenge, your strategic solution, the AI technologies utilized, your leadership role, and the quantifiable impact.

• Be prepared to discuss the trade-offs you made, the challenges you overcame, and what you learned from the experience.

• Use visuals where appropriate to illustrate product design, workflows, or data insights.

📝 Enhancement Note: Candidates should prepare to demonstrate not only their technical knowledge of AI but also their strategic thinking, leadership, and ability to communicate complex ideas effectively to diverse audiences. The portfolio presentation is a critical component.

📌 Application Steps

To apply for this operations position:

• Submit your application through the application link provided on Jobgether.

• Customize your resume: Highlight your experience in product management, AI strategy, agentic workflows, LLMs, and client consulting. Use keywords from the job description, especially specific AI platforms and methodologies. Quantify achievements with metrics where possible.

• Prepare your portfolio: Ensure it clearly showcases your experience in leading AI product development from conception to launch, with a focus on strategic impact and client outcomes. Be ready to present specific case studies that demonstrate your problem-solving skills and leadership.

• Research the partner company: Understand their focus areas, client base, and any publicly available information on their AI initiatives. This will help tailor your application and interview responses.

• Practice your interview responses: Prepare to articulate your experience with AI technologies, product strategy, and client management clearly and concisely, using the STAR method (Situation, Task, Action, Result) for behavioral questions.

⚠️ 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.