Remote Director of Product Strategy

📍 Job Overview

Job Title: Senior Product Manager - REMOTE

Company: Jobgether (on behalf of a partner company)

Location: Maine, United States (Remote)

Job Type: Full-time

Category: Product Management / Revenue Operations Enablement

Date Posted: May 09, 2026

Experience Level: Senior (8+ years)

Remote Status: Fully Remote

🚀 Role Summary

• Lead product strategy and roadmap definition for automation and compliance solutions within an enterprise B2B software context.

• Act as a player-coach, guiding a high-performing team through the full product development lifecycle, from ideation to launch.

• Drive key product initiatives that leverage AI-assisted tools to enhance efficiency and product capabilities.

• Establish and refine the team's operating model to maximize productivity and output in a fast-paced, ambiguous environment.

• Foster a strong customer-centric approach by maintaining a continuous feedback loop to validate product direction and ensure market fit.

📝 Enhancement Note: While the title is "Senior Product Manager," the core responsibilities heavily lean into areas critical for Revenue Operations (RevOps) and Sales Operations (Sales Ops) enablement, particularly concerning automation and compliance solutions. The emphasis on "driving product strategy" and "defining the development roadmap" for these specific solutions suggests a strong connection to optimizing internal GTM processes. The "player-coach" aspect and focus on operating models are also indicative of a role that bridges product development with operational efficiency. This role is ideal for someone who understands operational workflows and can translate those needs into product features, especially within a B2B enterprise software setting.

📈 Primary Responsibilities

• Own and meticulously define the product roadmap, ensuring strategic alignment with evolving customer needs and business objectives.

• Function as a player-coach, actively leading team members and participating in day-to-day product development activities to foster collaboration and drive execution.

• Spearhead critical product initiatives specifically focused on developing and enhancing automation and compliance solutions for enterprise clients.

• Design, implement, and refine the team's operating model to optimize overall performance, efficiency, and successful delivery of product outcomes.

• Champion and integrate the use of AI-assisted tools across the product development lifecycle to boost productivity, innovation, and solution quality.

• Cultivate and maintain a robust, ongoing feedback loop with customers to rigorously validate product direction, gather insights, and drive continuous improvement.

• Coordinate effectively with core product teams to ensure seamless integration of new features and solutions, maintaining a cohesive product ecosystem.

• Translate complex market opportunities and customer pain points into clear, actionable product requirements and user stories.

📝 Enhancement Note: The responsibilities highlight a strong focus on operational efficiency and GTM enablement through product development. The mention of "automation and compliance solutions" is particularly relevant to RevOps and Sales Ops, as these areas often require robust tools to streamline processes, ensure data integrity, and meet regulatory requirements. The player-coach model suggests hands-on involvement, which is common in roles that require deep understanding of how products are used to solve operational challenges.

🎓 Skills & Qualifications

Education:

• Bachelor's degree in a relevant field (e.g., Computer Science, Business, Engineering, Product Management).

Experience:

• Minimum of 8 years of progressive experience in product management, with a significant portion focused on enterprise B2B software.

• Demonstrated success in defining, developing, and successfully shipping new products, particularly within early-stage or dynamic environments.

• Proven ability to collaborate effectively with engineering teams, translating high-level requirements into detailed, actionable tasks and user stories.

• Exceptional customer engagement and discovery skills, with a knack for leading in-depth conversations to uncover unmet needs and validate product concepts.

• Experience thriving in fast-paced, often ambiguous environments where taking independent initiative and driving results are paramount.

Required Skills:

• Product Strategy: Ability to define and articulate a clear, compelling product vision and strategy.

• Product Roadmap Development: Expertise in creating and managing product roadmaps that align with business goals and customer needs.

• Enterprise B2B Software: Deep understanding of the enterprise B2B software market, its dynamics, and customer expectations.

• Customer Engagement & Discovery: Proven ability to conduct effective customer interviews, gather feedback, and translate insights into product requirements.

• Cross-functional Leadership: Skill in leading and influencing diverse teams (engineering, marketing, sales, operations) without direct authority.

• AI-assisted Tools Proficiency: Familiarity with leveraging AI and machine learning tools to enhance product development and features.

• Agile Methodologies: Experience working within Agile or Scrum frameworks for product development.

• Stakeholder Management: Strong capability to manage expectations and communicate effectively with all levels of stakeholders.

Preferred Skills:

• Automation & Compliance Solutions: Prior experience or deep understanding of developing products in these specific domains.

• Operating Model Design: Experience in establishing or optimizing team operating models for efficiency and effectiveness.

• Startup Environment Acumen: Ability to navigate ambiguity and drive rapid iteration common in startup-like settings.

• MBA or Advanced Degree: Demonstrates advanced business and strategic thinking capabilities.

📝 Enhancement Note: The experience requirement of "8+ years" and the emphasis on enterprise B2B software, coupled with the specific focus on automation and compliance, strongly suggests this role is at a senior level, likely equivalent to a Director or Senior Manager in a larger organization, or a lead PM in a growing company. The "player-coach" model implies a hands-on approach, so candidates should highlight instances where they actively contributed to execution while also providing strategic direction. The "AI-assisted tools" requirement is a key differentiator for modern product roles.

📊 Process & Systems Portfolio Requirements

Portfolio Essentials:

• Showcase a minimum of 2-3 detailed product case studies that demonstrate end-to-end product lifecycle management, from ideation to successful market launch.

• For each case study, clearly articulate the problem statement, the target customer segment, the product strategy employed, and the key features developed.

• Quantify the impact of your product initiatives using relevant metrics, such as adoption rates, revenue impact, cost savings, or efficiency gains achieved through automation.

• Provide examples of how you translated complex customer needs or operational challenges into actionable product requirements and user stories.

Process Documentation:

• Include examples of product requirement documents (PRDs), user stories, or feature specifications that illustrate your ability to clearly communicate product vision and technical requirements.

• Demonstrate your understanding of Agile development processes, potentially through a brief explanation of how you managed sprints, backlog grooming, or facilitated sprint reviews.

• Where applicable, showcase how you've contributed to defining or optimizing team operating models or workflows to enhance productivity and collaboration.

• Provide evidence of customer feedback mechanisms you've implemented or utilized to gather insights and validate product development.

📝 Enhancement Note: For a role involving product strategy and execution, especially with a focus on automation and compliance, a portfolio that showcases tangible results and a structured approach to product development is crucial. Candidates should be prepared to discuss the "why" behind their product decisions and demonstrate how they measured success, particularly in terms of operational efficiency or compliance adherence.

💵 Compensation & Benefits

Salary Range: $183,800 - $275,600 USD per year (This range is based on the provided information and represents a competitive offering for a Senior Product Manager role with significant responsibilities in the US market, considering the specified experience level and the company's focus on enterprise B2B software.)

Benefits:

• Performance-Based Incentives: Eligibility for an employee bonus program or commission structure, reflecting the company's performance-driven culture.

• Equity Opportunity: Potential to participate in an employee stock purchase plan, offering ownership and long-term financial upside.

• Comprehensive Health Coverage: Full suite of medical, dental, and vision insurance plans to support employee well-being.

• Financial Wellness: Access to flexible savings accounts (FSAs) and a matching 401K program to aid in financial planning and retirement savings.

• Work-Life Balance: Generous Paid Time Off (PTO) and Volunteer Time Off (VTO) policies to encourage personal time and community engagement.

• Support Systems: Robust employee assistance programs (EAPs) and dedicated mental health support resources.

• Professional Development: Opportunities for coaching and career growth, supporting continuous learning and advancement.

Working Hours:

• Standard full-time working hours are expected, likely around 40 hours per week, with flexibility inherent in a remote role. The "player-coach" aspect may require availability for team interactions and critical project phases.

📝 Enhancement Note: The salary range provided is substantial and aligns with senior-level product management roles in the US tech industry, especially for remote positions commanding specialized skills like AI integration and B2B enterprise software. The benefits package is comprehensive, emphasizing health, financial well-being, and work-life balance, which are attractive aspects for experienced professionals. The inclusion of both bonus/commission and stock purchase plan suggests a strong focus on both individual performance and company growth.

🎯 Team & Company Context

🏢 Company Culture

Industry: Enterprise B2B Software, potentially with a focus on SaaS solutions for automation, compliance, or GTM enablement.

Company Size: Indicated as a "partner company" of Jobgether, suggesting it's an established entity rather than a nascent startup, likely mid-to-large size, capable of offering comprehensive benefits and structured career paths.

Founded: Not specified, but the context implies a company with a market presence and established product lines.

Team Structure:

• The role leads a "focused team" operating with "startup speed and innovation" but within a "market leader's expertise." This suggests a dedicated product squad or pod structure focused on a specific product area or initiative.

• The team likely includes engineers, designers, and potentially product marketing or operations specialists, with the Senior Product Manager acting as the central orchestrator.

Methodology:

• Data-Driven Product Development: Emphasis on customer feedback loops and leveraging data (likely product analytics and market research) to inform strategy and roadmap decisions.

• Agile Execution: The "startup speed" and "player-coach" model point towards agile development methodologies for rapid iteration and delivery.

• AI Integration: A proactive approach to incorporating AI-assisted tools to enhance development processes and product capabilities.

• Operating Model Optimization: A focus on defining and refining team processes to maximize efficiency and output.

Company Website: [Partner Company Website - Not specified, but Jobgether's domain is jobgether.com]

📝 Enhancement Note: The description paints a picture of a dynamic, results-oriented environment that balances the agility of a startup with the stability and resources of a larger organization. For operations professionals, this means a chance to influence product development that directly impacts their workflows, with a team that values efficiency and innovation.

📈 Career & Growth Analysis

Operations Career Level: This role is positioned as a "Senior Product Manager," implying a significant level of autonomy, strategic responsibility, and experience. In a larger organization, this could translate to a leadership role within a specific product domain or a path towards Group Product Manager or Director of Product. For a company focused on GTM enablement, this role's impact on automation and compliance directly supports operational efficiency and scalability.

Reporting Structure: The Senior Product Manager will likely report to a Director of Product or VP of Product. They will lead a dedicated product team and collaborate extensively with Engineering Managers, GTM leaders (e.g., VPs of Sales Operations, Revenue Operations), and potentially executive stakeholders.

Operations Impact: This role has a direct and significant impact on operational efficiency and effectiveness. By driving the strategy and roadmap for automation and compliance solutions, the Senior Product Manager will enable sales, marketing, and customer success teams to operate more smoothly, reduce manual effort, ensure data integrity, and meet regulatory requirements. This can lead to increased productivity, reduced operational costs, and improved customer experience.

Growth Opportunities:

• Product Leadership: Potential to advance into management roles, leading larger product teams or entire product lines.

• Specialization: Deepen expertise in specific areas like AI in product development, automation solutions, or compliance technology.

• Strategic Influence: Gain opportunities to shape broader company product strategy and contribute to business-level decision-making.

• Cross-functional Mobility: Develop strong relationships across GTM functions, potentially leading to opportunities in operations, strategy, or business development roles.

• Mentorship: Opportunities to mentor junior product managers and contribute to the growth of the product organization.

📝 Enhancement Note: The emphasis on automation and compliance solutions makes this role particularly attractive for individuals with a background or strong interest in the operational aspects of a business. The growth opportunities are substantial, offering a clear path for career advancement within product management or related strategic functions.

🌐 Work Environment

Office Type: Fully Remote. This indicates a distributed workforce model, emphasizing asynchronous communication and digital collaboration tools.

Office Location(s): While the role is remote, the derived location is Maine, United States, suggesting that the primary company or at least the relevant legal/HR entity might be registered or have a strong presence there. However, the role is open to remote candidates, likely within the US.

Workspace Context:

• Digital Collaboration: Expect a heavy reliance on tools like Slack, Zoom, Google Workspace, Jira, Confluence, and potentially specialized collaboration platforms for remote teams.

• Asynchronous Communication: Emphasis on clear, documented communication to accommodate different time zones and working schedules.

• Autonomy & Trust: A remote environment that values self-starters who can manage their time effectively and deliver results independently.

• Virtual Team Building: The company likely invests in virtual team-building activities and communication strategies to foster cohesion and culture among remote employees.

Work Schedule: While a standard 40-hour work week is implied for full-time employment, the remote nature likely offers some flexibility in terms of daily scheduling, though core meeting times and team syncs will be established. The "player-coach" role may require adaptability to team needs and project deadlines.

📝 Enhancement Note: For operations professionals accustomed to structured environments, the remote nature requires strong self-discipline and proactive communication. The company's engagement with Jobgether suggests a modern approach to talent acquisition and management, likely with robust support for remote employees.

📄 Application & Portfolio Review Process

Interview Process:

• Initial Screening (Jobgether AI): Your application will be processed by Jobgether's AI for initial matching against core requirements.

• Company Screening: Qualified candidates will be contacted by the partner company for an initial conversation, likely with an HR representative or hiring manager, to assess fit and interest.

• Hiring Manager Interview: A deep dive into your product management experience, strategic thinking, and technical understanding, focusing on your ability to lead the team and drive product initiatives. Expect questions about your approach to roadmap development, customer discovery, and AI integration.

• Team/Cross-functional Interviews: Meetings with key team members (engineering, potentially operations or GTM stakeholders) to evaluate collaboration style, technical acumen, and cultural fit.

• Portfolio Presentation/Case Study: You will likely be asked to present a case study from your portfolio, detailing a product you’ve brought to market, focusing on strategy, execution, and impact. Be prepared to discuss challenges, trade-offs, and lessons learned.

• Executive Interview: A final conversation with senior leadership (e.g., VP of Product, CPO) to assess strategic alignment, leadership potential, and overall fit with the company's vision.

Portfolio Review Tips:

• Quantify Everything: For each case study, use hard numbers to demonstrate the impact of your product. Focus on metrics related to efficiency, cost savings, adoption, revenue, or compliance adherence.

• Tell a Story: Structure your portfolio presentations as narratives. Clearly articulate the problem, your solution, the process you followed, and the measurable outcomes.

• Highlight Operations Relevance: Since the role focuses on automation and compliance, emphasize how your past products have streamlined operations, improved data integrity, or ensured regulatory adherence.

• Showcase AI Experience: If you have experience with AI in product development, make it a prominent part of your presentation. Discuss how you leveraged it, the challenges, and the benefits.

• Prepare for "Why": Be ready to explain the strategic rationale behind your product decisions and roadmap priorities.

Challenge Preparation:

• Product Strategy Exercise: You might be given a hypothetical product challenge or asked to outline a strategy for a new feature or market entry. Focus on a structured approach: market analysis, customer segmentation, value proposition, and key initiatives.

• Technical Acumen: Be prepared to discuss technical concepts relevant to B2B software, APIs, data management, and AI integration at a high level.

• Operating Model Discussion: Be ready to discuss your experience in defining or optimizing team processes and operating models for efficiency.

📝 Enhancement Note: The emphasis on a portfolio and case studies is critical. Candidates should prepare to walk through their most impactful projects, clearly articulating their role, the challenges faced, the strategies employed, and the quantifiable results achieved, with a particular eye toward operational improvements.

🛠 Tools & Technology Stack

Primary Tools:

• Product Management Platforms: Jira, Confluence, Asana, or similar for backlog management, sprint planning, and documentation.

• Prototyping & Design Tools: Figma, Sketch, Adobe XD, or InVision for wireframing and mockups.

• Collaboration Suites: Slack, Microsoft Teams for instant communication and team coordination.

• Video Conferencing: Zoom, Google Meet for virtual meetings and team syncs.

Analytics & Reporting:

• Product Analytics: Amplitude, Mixpanel, Google Analytics for tracking user behavior and feature adoption.

• Business Intelligence Tools: Tableau, Power BI, Looker for analyzing business performance and operational metrics.

• CRM Data: Salesforce, HubSpot (understanding how product features integrate with and impact CRM data is key for RevOps alignment).

CRM & Automation:

• CRM Systems: Salesforce, HubSpot (understanding user workflows and data needs within these systems).

• Automation Platforms: Experience with or understanding of how products integrate with or automate workflows within systems like Zapier, Workato, or custom RPA solutions.

• AI/ML Platforms: Familiarity with AI/ML development tools or platforms (e.g., TensorFlow, PyTorch, cloud AI services) is a plus, especially for understanding how AI features are built and integrated.

📝 Enhancement Note: A strong understanding of how products interact with CRM systems and contribute to automation workflows is highly relevant for this role, given its focus on RevOps/Sales Ops enablement. Proficiency in Agile tools like Jira is a given, and familiarity with product analytics platforms is essential for data-driven decision-making.

👥 Team Culture & Values

Operations Values:

• Customer Centricity: A deep commitment to understanding and solving customer problems, particularly those related to operational efficiency and compliance.

• Innovation & Agility: Embracing new technologies (like AI) and methodologies to drive rapid product development and adapt to market changes.

• Data-Driven Decision Making: Relying on data, customer feedback, and rigorous analysis to inform product strategy and execution.

• Collaboration & Transparency: Fostering an open environment where team members can share ideas, provide feedback, and work together effectively across functions.

• Ownership & Accountability: Taking responsibility for product outcomes and driving initiatives to successful completion.

Collaboration Style:

• Cross-functional Integration: A strong emphasis on working closely with engineering, design, marketing, sales, and operations teams to ensure product success.

• Player-Coach Mentality: Encouraging a hands-on approach where leaders actively contribute to execution while guiding and mentoring their teams.

• Feedback-Rich Environment: Valuing constructive feedback as a tool for continuous improvement at both the individual and team level.

• Process Optimization Focus: A shared drive to identify inefficiencies and implement solutions that streamline workflows and enhance productivity.

📝 Enhancement Note: The culture described is one that values both strategic thinking and hands-on execution, with a strong emphasis on leveraging technology to solve business problems. For operations professionals, this means a collaborative environment where their insights into workflow challenges can directly inform product development priorities.

⚡ Challenges & Growth Opportunities

Challenges:

• Navigating Ambiguity: Operating in a fast-paced environment that may involve shifting priorities and evolving market demands. Candidates need to be comfortable with uncertainty and able to drive clarity.

• Balancing Strategic Vision with Execution: Effectively translating high-level product strategy into actionable tasks for the team while ensuring day-to-day progress.

• Cross-functional Alignment: Gaining buy-in and maintaining alignment across diverse stakeholder groups with potentially competing priorities.

• AI Integration Complexity: Successfully integrating AI-assisted tools and features into products requires technical understanding, ethical considerations, and user adoption strategies.

• Defining and Optimizing Operating Models: Establishing effective team structures and processes that maximize efficiency in a remote, dynamic setting.

Learning & Development Opportunities:

• Advanced Product Strategy: Deepen expertise in market analysis, competitive landscaping, and long-term product vision setting.

• AI/ML Product Development: Gain hands-on experience with cutting-edge AI technologies and their application in enterprise software.

• Operational Excellence: Develop a stronger understanding of GTM operations, automation, and compliance through close collaboration with relevant teams.

• Leadership Development: Hone skills in team leadership, mentoring, and influencing through the player-coach model and potential for management growth.

• Industry Exposure: Opportunities to learn about emerging trends in enterprise B2B software, automation, and AI through company initiatives and potentially industry events.

📝 Enhancement Note: The challenges presented are typical for senior product roles in innovative tech companies. The growth opportunities are substantial, particularly for those looking to blend product expertise with a deep understanding of operational efficiency and emerging technologies like AI.

💡 Interview Preparation

Strategy Questions:

• "Describe a time you defined a product strategy for a complex B2B solution. What was your process, and what were the key outcomes?" (Focus on structured approach, market analysis, and quantifiable results).

• "How would you approach building a product roadmap for automation solutions, considering competing priorities and limited resources?" (Highlight prioritization frameworks, customer validation, and alignment with business goals).

• "Walk me through your experience using AI-assisted tools in product development. What were the benefits and challenges?" (Be ready to discuss specific tools, impact on productivity, and any ethical considerations).

Company & Culture Questions:

• "What interests you most about this role and our company's focus on automation and compliance?" (Research the partner company if possible, and connect your skills to their mission).

• "How do you foster collaboration within a remote team, especially with engineering and operational stakeholders?" (Provide examples of communication strategies, virtual team-building, and conflict resolution).

Portfolio Presentation Strategy:

• Structure Your Narrative: Begin with the problem, introduce the customer, explain your strategic approach, detail the solution you built, and conclude with quantifiable results.

• Focus on Impact: Emphasize metrics related to efficiency gains, cost reduction, improved compliance, increased adoption, or revenue growth.

• Explain Your Role: Clearly articulate your specific contributions and decision-making processes.

• Be Ready for Deep Dives: Anticipate questions about trade-offs, challenges, competitor analysis, and future iterations.

• Tailor to the Role: Highlight aspects of your case studies that directly relate to automation, compliance, B2B enterprise software, or AI integration.

📝 Enhancement Note: Candidates should prepare to discuss their strategic thinking, leadership capabilities, and hands-on product development experience with a strong emphasis on quantifiable results and operational impact. The portfolio presentation is a critical component, so thorough preparation is essential.

📌 Application Steps

To apply for this operations-enabling product position:

• Submit your application through the provided application link, ensuring all fields are completed accurately.

• Portfolio Customization: Select 2-3 of your most impactful product case studies that best demonstrate your experience in B2B enterprise software, especially those involving automation, compliance, or AI. Quantify results and clearly articulate your strategic contributions.

• Resume Optimization: Tailor your resume to highlight your 8+ years of product management experience in enterprise B2B software. Use keywords from the job description (e.g., "product strategy," "roadmap," "automation," "compliance," "AI-assisted tools," "customer discovery," "stakeholder management").

• Interview Preparation: Practice articulating your experience using the STAR method. Prepare to discuss your portfolio case studies in detail and be ready to answer strategic and behavioral questions related to product leadership and operations enablement.

• Company Research: If possible, research the partner company to understand their specific market, product offerings, and any public information about their culture or recent news. This will help you tailor your responses and demonstrate genuine interest.

⚠️ 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.