Senior Product Manager (AI Evaluation & Product Strategy) at Gramian Consulting Group

📍 Job Overview

Job Title: Senior Product Manager (AI Evaluation & Product Strategy)

Company: Gramian Consulting Group

Location: United States

Job Type: CONTRACTOR

Category: Product Management / GTM Operations

Date Posted: 2026-08-24

Experience Level: 5-10 Years

Remote Status: Remote Solely

🚀 Role Summary

This role is critical for defining and evaluating the quality of AI-generated product management outputs, ensuring they align with industry best practices and senior-level expectations.
Key responsibilities include designing realistic product management scenarios and creating exemplary deliverables such as Product Requirements Documents (PRDs), roadmaps, and launch memos.
The position requires a deep understanding of product strategy, prioritization frameworks, and cross-functional communication within a high-scale technology environment.
Successful candidates will leverage their extensive product management experience to establish evaluation rubrics and provide structured feedback to enhance AI-driven product development processes.

📝 Enhancement Note: While the job title is "Senior Product Manager," the core function described leans heavily into the operational aspects of defining standards, evaluating outputs, and refining processes for AI-generated product materials. This positions the role within a GTM Operations or Product Operations framework, focusing on the how of product management execution and quality assurance rather than direct product ownership.

📈 Primary Responsibilities

Design and document realistic product management scenarios that simulate complex real-world workflows, decision-making processes, and trade-offs faced by senior Product Managers.
Create "gold-standard" reference deliverables including comprehensive Product Requirements Documents (PRDs), detailed product roadmaps, impactful launch memos, executive-level updates, and clear cross-functional briefs.
Develop sophisticated product strategy scenarios, focusing on critical elements such as effective prioritization, strategic trade-offs, deep customer need analysis, and sound execution decisions.
Critically evaluate AI-generated product management deliverables, assessing them for structural integrity, logical reasoning, technical depth, clarity for various stakeholders, and overall quality against established benchmarks.
Define, refine, and meticulously detail evaluation rubrics and scoring mechanisms for senior-level product management outputs, ensuring objective and consistent assessment.
Identify and articulate common weaknesses in AI-generated content, such as vague objectives, insufficient trade-off analysis, weak prioritization logic, or unclear success criteria, to guide AI model improvement.
Apply established and recognized Product Management frameworks, such as Jobs-to-be-Done (JTBD), Opportunity Solution Trees, or various prioritization models, in both the creation of scenarios and the evaluation of outputs.
Ensure all created scenarios and synthesized deliverables authentically represent high-impact product workflows and decision-making processes characteristic of leading technology companies.
Provide structured, actionable, and constructive feedback to AI development teams to improve the quality and efficacy of AI-generated product management outputs.

📝 Enhancement Note: The responsibilities emphasize a strong focus on process definition, quality assurance, and the creation of standardized outputs, which are hallmarks of operational roles. The evaluation of AI outputs points towards a need for systematic analysis and a deep understanding of product management best practices.

🎓 Skills & Qualifications

Education: Bachelor's degree in Computer Science, Engineering, Business, or a related field is typically expected for senior product roles, though extensive relevant experience can often substitute.

Experience: Minimum of 4 years of professional Product Management experience, with a strong preference for candidates with experience in major technology companies (e.g., FAANG) or comparable high-scale, high-growth product environments. Hands-on ownership of key product documentation and strategic artifacts is essential.

Required Skills:

Product Management Expertise: Proven track record of successfully managing products from ideation through launch and iteration.
Product Strategy & Roadmapping: Demonstrated ability to define and articulate product vision, strategy, and develop actionable roadmaps.
PRD & Documentation Creation: Expertise in authoring comprehensive, clear, and decision-oriented Product Requirements Documents (PRDs), launch memos, and executive presentations.
Prioritization Frameworks: Practical knowledge and application of PM frameworks such as Jobs-to-be-Done (JTBD), Opportunity Solution Trees, or various prioritization models (e.g., RICE, MoSCoW).
Cross-functional Collaboration: Extensive experience working effectively with engineering, design, data science, marketing, sales, and other business stakeholders.
Analytical & Critical Thinking: Strong ability to analyze complex problems, evaluate AI-generated content, and identify areas for improvement with a focus on technical depth and reasoning.
Written Communication: Exceptional written English skills, with a proven ability to communicate complex ideas clearly and persuasively to both technical and executive audiences.
Stakeholder Management: Ability to manage expectations and communicate effectively with diverse stakeholder groups.

Preferred Skills:

Experience in AI product development or evaluating AI-driven tools.
Familiarity with specific AI evaluation methodologies or quality assurance processes.
Experience working within a consultancy environment, understanding client needs and project-based work.
Direct experience in defining or refining evaluation criteria for automated systems or AI outputs.
Advanced degrees (e.g., MBA, Master's in a technical field) may be advantageous.

📝 Enhancement Note: The emphasis on specific PM frameworks and experience in high-scale environments suggests a need for candidates who can not only perform product management tasks but also critically analyze and articulate the underlying principles and best practices. The "AI Evaluation" aspect implies a need for analytical rigor beyond standard PM duties.

📊 Process & Systems Portfolio Requirements

Portfolio Essentials:

Demonstrated Product Deliverables: Showcase examples of Product Requirements Documents (PRDs), roadmaps, and launch memos that you have personally authored and managed. These should highlight your ability to create clear, comprehensive, and decision-oriented documentation.
Product Strategy Artifacts: Include examples of product strategy documents, prioritization frameworks applied to real-world scenarios, or case studies detailing how you developed and executed a product strategy.
AI Evaluation Case Studies (if applicable): If you have experience evaluating AI outputs or defining quality standards for automated systems, present case studies demonstrating your analytical approach and impact.
Cross-functional Collaboration Examples: Provide examples or case studies that illustrate your ability to collaborate effectively with engineering, design, and business teams, showcasing how you managed dependencies and achieved shared goals.

Process Documentation:

Workflow Design & Optimization: Demonstrate your ability to document existing product management workflows, identify inefficiencies, and propose optimized processes for scenario creation, deliverable generation, and AI output evaluation.
Implementation & Automation: Showcase experience in implementing new processes or utilizing tools to streamline product management tasks, including how you might integrate AI-generated content into existing workflows or evaluation systems.
Measurement & Performance Analysis: Illustrate how you would measure the effectiveness of AI-generated product management outputs and the success of your evaluation rubrics, using metrics related to quality, efficiency, and alignment with best practices.

📝 Enhancement Note: Given the role's focus on defining and evaluating AI-generated product management work, a portfolio demonstrating not just what was produced but how it was conceived, prioritized, and evaluated will be crucial. Candidates should be prepared to articulate the thought process behind their deliverables and their approach to quality assurance.

💵 Compensation & Benefits

Salary Range: $60 - $100 per hour. This range reflects a contractor position requiring significant senior-level product management expertise and experience in high-scale technology environments. The specific rate will depend on the candidate's experience, qualifications, and alignment with the specific requirements of the project.

Benefits:

Flexible Work Arrangement: Fully remote position, allowing for work from any location within the United States.
Contract Engagement: Opportunity to work on a project-specific basis, offering flexibility and exposure to diverse product challenges.
Competitive Hourly Rate: Compensation commensurate with senior-level product management expertise and the specialized nature of AI evaluation.
Professional Development: Exposure to cutting-edge AI evaluation methodologies and the opportunity to shape best practices in AI-assisted product management.
Potential for Future Engagements: Successful contractors may be considered for future projects with Gramian Consulting Group.

Working Hours: This is a contractor role, and while the standard expectation is approximately 40 hours per week, flexibility may be available based on project needs and agreement with Gramian Consulting Group. The focus will be on delivering high-quality outcomes and meeting project deadlines.

📝 Enhancement Note: The specified hourly rate of $60-$100 per hour for a contractor role in the United States aligns with industry standards for experienced Product Managers, particularly those with specialized skills in AI evaluation or strategic product development. This rate often accounts for the lack of traditional employee benefits like health insurance, paid time off, and retirement contributions, which are typically the responsibility of the contractor.

🎯 Team & Company Context

🏢 Company Culture

Industry: IT Professional Services and Engineering Talent Solutions. Gramian Consulting Group operates within the technology services sector, acting as a bridge between companies seeking specialized IT talent and skilled professionals.

Company Size: Boutique consultancy. This suggests a focused, agile team environment where individual contributions are highly visible and impactful. For operations professionals, this often means direct access to leadership and the ability to influence processes.

Founded: Information not explicitly provided, but the company positions itself with a "strong background in software engineering and leadership," implying established expertise.

Team Structure:

Consultancy Model: The team likely consists of experienced consultants and talent acquisition specialists. As a contractor, you would operate as an external expert, collaborating with internal project managers or client-side teams.
Project-Based: Work is organized around client projects, requiring adaptability and strong project management skills.
Cross-Functional Collaboration: You will collaborate with Gramian's internal teams (if applicable) and, more significantly, with client-side engineering, product, and leadership teams.

Methodology:

Talent Matching Focus: Gramian's core methodology revolves around understanding client needs deeply to provide precisely matched engineering and IT talent.
Quality Assurance: The role emphasizes defining and ensuring high-quality outputs, mirroring a quality assurance function within a product development lifecycle.
Process Refinement: The need to evaluate AI outputs and define rubrics suggests a culture that values process improvement and operational excellence.

Company Website: https://jobs.workable.com/company/kANY7hHLXDH7fUqyifRLmf/jobs-at-gramian-consulting-group

📝 Enhancement Note: As a boutique consultancy, Gramian likely prioritizes deep expertise and client-centric solutions. For a contractor in this role, success will hinge on demonstrating not just PM skills but also the ability to act as a subject matter expert in evaluating and setting standards for AI-generated product work.

📈 Career & Growth Analysis

Operations Career Level: This role is positioned at a senior individual contributor level, focusing on specialized expertise in product management evaluation. It's an opportunity to leverage extensive PM experience in a unique capacity, contributing to the operational framework of AI-assisted product development.

Reporting Structure: As a contractor, you will likely report to a project manager or a lead consultant at Gramian Consulting Group, and work closely with client-side product leadership or AI development teams.

Operations Impact: Your work will directly impact the quality and effectiveness of AI tools used in product management, influencing how product strategies are developed, documented, and evaluated. This contributes to more efficient and higher-quality product development cycles for Gramian's clients.

Growth Opportunities:

Specialized Skill Development: Deepen expertise in AI evaluation, AI product strategy, and the operationalization of AI in product management workflows.
Broader Industry Exposure: Gain exposure to diverse product challenges and AI applications across various client companies within Gramian's portfolio.
Consulting Acumen: Develop skills in client management, project delivery, and defining operational best practices for technology services.
Potential for Future Engagements: Successful performance can lead to ongoing contract opportunities with Gramian Consulting Group and its clients.

📝 Enhancement Note: This role offers a unique growth path by bridging traditional product management with the emerging field of AI evaluation. It's an opportunity to become a subject matter expert in a high-demand area, offering a distinct advantage for future roles in product operations or AI strategy.

🌐 Work Environment

Office Type: Fully Remote (TELECOMMUTE). This role is designed for individuals who can work independently and effectively from their own location within the United States.

Office Location(s): United States. While remote, candidates must be based in the US to comply with any potential client or operational requirements.

Workspace Context:

Independent Work: Requires a dedicated, professional workspace conducive to focused work, scenario design, and detailed documentation.
Digital Collaboration: Heavy reliance on digital communication tools (e.g., Slack, Zoom, email) for interaction with Gramian project managers and client teams.
Self-Management: Emphasis on self-discipline, time management, and proactive communication to ensure project milestones are met without direct physical supervision.

Work Schedule: Approximately 40 hours per week, with potential flexibility. The focus is on task completion and meeting project deadlines rather than adhering to rigid daily schedules. Effective time management across different time zones (if collaborating with distributed teams) will be important.

📝 Enhancement Note: The remote nature of this role necessitates strong self-management and communication skills. Candidates should be adept at working autonomously and ensuring seamless collaboration through digital channels.

📄 Application & Portfolio Review Process

Interview Process:

Initial Screening: Likely a review of your resume and portfolio, focusing on your product management experience, scale of previous roles, and specific documentation examples.
Skills Assessment: May involve a take-home assignment or a live exercise where you are asked to design a product scenario or evaluate an AI-generated output. This will test your practical skills and adherence to PM frameworks.
Case Study Presentation: You may be asked to present a detailed case study from your portfolio, explaining your process, decisions, and the impact of your work, particularly focusing on documentation and strategic thinking.
Behavioral & Cultural Fit: Interviews will assess your communication style, problem-solving approach, ability to handle ambiguity, and how you provide constructive feedback – crucial for this role.

Portfolio Review Tips:

Curate Strategically: Select examples of PRDs, roadmaps, and strategy documents that best showcase your ability to create clear, comprehensive, and decision-oriented outputs, especially those from high-scale environments.
Highlight Process: For each portfolio item, be prepared to articulate your thought process, the frameworks you used (e.g., JTBD, opportunity solution trees), the trade-offs you considered, and how you collaborated with stakeholders.
Quantify Impact: Wherever possible, include metrics or outcomes that demonstrate the success or impact of your product work. For this role, emphasize the quality and clarity of your documentation.
Address AI Evaluation: If you have relevant experience, prepare to discuss your approach to evaluating AI-generated content, identifying its strengths and weaknesses, and providing actionable feedback. If not, articulate how you would approach this task based on your PM expertise.
Tailor to the Role: Emphasize experience with executive reviews, prioritization, and cross-functional communication, as these are core to the job description.

Challenge Preparation:

Scenario Design: Practice creating realistic product scenarios that require strategic thinking and decision-making. Consider common challenges in tech product development (e.g., new feature prioritization, competitive responses, market entry).
Deliverable Quality: Review best practices for PRD writing, roadmap articulation, and launch memo structure. Focus on clarity, conciseness, and ensuring all key stakeholders' needs are addressed.
AI Evaluation Framework: Think about how you would assess the quality of AI-generated content. What criteria would you use? How would you ensure objectivity? Consider aspects like completeness, accuracy, logical flow, and alignment with user needs and business goals.

📝 Enhancement Note: The emphasis on portfolio and practical application suggests that candidates who can clearly demonstrate their process, critical thinking, and ability to produce high-quality documentation will have a significant advantage. Preparing to articulate the "why" behind decisions is key.

🛠 Tools & Technology Stack

Primary Tools:

Product Management Software: Proficiency with tools such as Jira, Confluence, Asana, or similar for documentation, task management, and workflow tracking.
Roadmapping Tools: Experience with tools like Aha!, Productboard, Roadmunk, or even advanced spreadsheet/presentation software for roadmap development and visualization.
Collaboration Platforms: Deep familiarity with tools like Slack, Microsoft Teams, Google Workspace (Docs, Sheets, Slides) for day-to-day communication and document creation.

Analytics & Reporting:

Data Analysis Tools: While not directly managing data, understanding how to interpret data from tools like Amplitude, Mixpanel, Google Analytics, or internal BI platforms is beneficial for grounding product decisions.
Presentation Software: Strong command of PowerPoint, Google Slides, or Keynote for creating executive-level presentations and reports.

CRM & Automation:

CRM Systems: Familiarity with CRM platforms like Salesforce, HubSpot, or similar is helpful for understanding customer data and sales/marketing alignment, though not a primary focus of this role.
AI/ML Platforms (Exposure): While no prior AI experience is required, an understanding of how AI models are developed and deployed, or exposure to AI evaluation tools, would be a plus.

📝 Enhancement Note: The technology stack primarily revolves around standard product management and collaboration tools. The key differentiator will be the ability to apply these tools and principles to the evaluation of AI-generated content, rather than the specific AI tools themselves.

👥 Team Culture & Values

Operations Values:

Excellence in Execution: A commitment to producing high-quality, polished deliverables that meet rigorous standards, mirroring senior-level product management output.
Analytical Rigor: A data-driven and analytical approach to problem-solving, scenario design, and critically evaluating AI-generated content.
Process Orientation: A focus on defining, refining, and adhering to structured processes for creating and assessing product management artifacts.
Clarity & Precision: Valuing clear, concise, and unambiguous communication in all documentation and stakeholder interactions.
Continuous Improvement: An openness to evolving methodologies, especially concerning AI integration, and a drive to enhance efficiency and effectiveness.

Collaboration Style:

Expert Collaboration: Working as a subject matter expert, providing authoritative insights and guidance to both Gramian's internal teams and client stakeholders.
Constructive Feedback: Delivering feedback in a professional, actionable, and supportive manner, aimed at improving AI outputs and processes.
Cross-functional Partnership: Engaging effectively with diverse teams (engineering, design, business) to ensure alignment and comprehensive understanding of product requirements and strategies.
Proactive Communication: Maintaining open lines of communication, especially in a remote setting, to ensure project transparency and address potential issues promptly.

📝 Enhancement Note: The emphasis on "boutique consultancy" and "senior-level PM work" suggests a culture that values deep expertise, meticulous execution, and professional integrity. Collaboration will likely be focused on delivering high-value strategic insights.

⚡ Challenges & Growth Opportunities

Challenges:

Defining "Excellence": Establishing objective and consistent criteria for evaluating AI-generated product management outputs, which can be subjective.
Bridging AI & Human Expertise: Effectively translating complex human product management intuition and experience into evaluable criteria for AI systems.
Remote Collaboration: Maintaining strong communication and influence without direct in-person interaction, ensuring alignment with diverse client teams.
Pacing & Scope Management: Balancing the creation of high-quality scenarios and deliverables with the demands of a contractor assignment and potentially evolving project scopes.

Learning & Development Opportunities:

AI Product Operations Expertise: Becoming a go-to expert in the operationalization of AI within product management workflows.
Consulting Skills Enhancement: Developing client-facing skills, project management, and advisory capabilities within a professional services context.
Exposure to AI Innovation: Gaining insights into the latest advancements in AI and their practical applications in product development.
Strategic Impact: Contributing to defining the future of product management by shaping AI-driven tools and processes.

📝 Enhancement Note: This role presents a unique opportunity to tackle the emerging challenges at the intersection of AI and product management. Success will require adaptability, strong analytical skills, and a proactive approach to learning.

💡 Interview Preparation

Strategy Questions:

"Describe a time you had to define a new process or standard for product management within your team or organization. How did you approach it, and what was the outcome?" (Focus on your ability to create evaluation rubrics and define standards).
"Walk us through your process for creating a Product Requirements Document (PRD). What are the key sections, what information is critical, and how do you ensure buy-in from stakeholders?" (Demonstrate your documentation skills and understanding of PM frameworks).
"How would you evaluate an AI-generated product strategy document? What are the key indicators of quality, and what are common pitfalls you would look for?" (Directly assess your ability to perform the core function of the role). Company & Culture Questions:
"Given our focus as a boutique consultancy specializing in IT talent and professional services, how do you see your role in evaluating AI product outputs contributing to our clients' success?" (Connect your skills to Gramian's business model and client value).
"How do you approach providing constructive feedback, especially when it might be critical of an AI's output or a client's existing processes?" (Assess your communication and collaboration style).
"What do you consider 'gold-standard' product management work, and how would you translate that into criteria for evaluating AI-generated content?" (Gauge your understanding of senior-level PM expectations). Portfolio Presentation Strategy:
Structure Your Narrative: For each portfolio example (PRD, roadmap, strategy), clearly articulate the problem, your approach (including frameworks used), the key decisions and trade-offs, the collaborative process, and the final outcome or impact.
Highlight Process Over Product: While the deliverables are important, focus on explaining your thinking and process. This is crucial for demonstrating your ability to evaluate and define quality.
Quantify Where Possible: Use metrics to support your claims about impact or efficiency, but also be prepared to discuss qualitative improvements.
Address the AI Aspect: If you have direct AI evaluation experience, highlight it. If not, explain how your PM experience and analytical skills would enable you to effectively evaluate AI-generated content and define quality standards.

📝 Enhancement Note: Prepare to speak extensively about your process, your rationale behind decisions, and your ability to articulate complex product concepts clearly. The interview will likely focus on assessing your expertise in product management fundamentals and your analytical approach to evaluating AI outputs.

📌 Application Steps

To apply for this operations position:

Submit your application through the provided link on Workable.
Curate Your Portfolio: Select 2-3 key pieces of work (e.g., a comprehensive PRD, a strategic roadmap, a launch memo) that best demonstrate your senior-level product management capabilities, focusing on clarity, depth, and strategic thinking. Be prepared to discuss the context, your decision-making process, and the outcomes.
Optimize Your Resume: Tailor your resume to highlight your experience in product strategy, PRD creation, roadmap development, and any experience with defining standards or evaluating complex outputs. Use keywords from the job description like "Product Strategy," "PRD," "Roadmap," "AI Evaluation," and "Cross-functional Communication."
Prepare for a Scenario Exercise: Anticipate a task where you might be asked to design a product scenario or evaluate an AI-generated deliverable. Practice articulating your thought process and the criteria you would use for assessment.
Research Gramian Consulting Group: Understand their business model as a boutique consultancy focused on IT professional services and talent solutions. Consider how your role contributes to their client offerings and value proposition.

⚠️ 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.

Senior Product Manager (AI Evaluation & Product Strategy)