Head of Product Strategy

📍 Job Overview

Job Title: Head of Product Strategy

Company: Acclaim (Overtime.ai)

Location: Austin, Texas, United States

Job Type: Full-time

Category: Product Strategy / Product Management (with a strong Operations focus)

Date Posted: May 20, 2026

Experience Level: 10+ Years (as inferred from "8 years" requirement and leadership title)

Remote Status: On-site

🚀 Role Summary

• Owns the end-to-end product roadmap development and execution for AI-driven platforms, ensuring alignment with long-term vision and near-term operational realities.

• Acts as the critical liaison between business stakeholders, engineering, operations, and compliance to translate complex needs into clear product specifications and actionable delivery plans.

• Drives the prioritization of platform investments, focusing on AI capabilities, automation, voice technology, integrations, and compliance controls within a regulated industry context.

• Establishes and maintains robust feedback loops across all client-facing and internal teams to continuously inform product enhancements and identify operational efficiencies.

• Ensures product development directly addresses client needs and scales effectively within operational workflows, particularly in regulated environments like fintech and healthcare RCM.

📝 Enhancement Note: The title "Head of Product Strategy" combined with the responsibility for "what gets built" and "platform direction" strongly suggests a senior leadership role with significant influence over the product lifecycle. The emphasis on "operations on what's deployable" and "client delivery" positions this role as a key bridge between technical development and practical, scalable implementation, aligning closely with Revenue Operations and Sales Operations principles of driving efficiency and effectiveness. The description also highlights a need for understanding regulated environments, which adds a layer of complexity and compliance focus often found in GTM operations.

📈 Primary Responsibilities

• Roadmap Ownership: Define and manage the multi-quarter product roadmap, coordinating stakeholder input, sequencing feature releases, and ensuring disciplined execution with clear timelines and dependency management.

• Client-to-Product Translation: Convert client requirements, implementation feedback, operational workflows, and compliance mandates into detailed, sequenced product specifications for engineering teams.

• Strategic Prioritization: Partner with CTO and engineering leadership to prioritize investments in AI, automation, voice technology, integrations, compliance, and reporting, making defensible trade-off decisions.

• AI Capability Definition: Define product requirements for new AI features, compliance enhancements, reporting tools, and user experience improvements in collaboration with engineering and applied AI specialists.

• Operational Bridge Function: Serve as the primary intermediary between business units (operations, sales, client success) and engineering, resolving day-to-day friction and ensuring smooth communication of priorities and constraints.

• Implementation & Onboarding Alignment: Maintain close proximity to implementation and onboarding processes to ensure product decisions are practical and reflect real-world deployment challenges, preventing surprises for deployment teams.

• Feedback Loop Management: Establish and manage structured feedback mechanisms with operations, sales, compliance, client success, and engineering teams, ensuring insights are captured and used for roadmap prioritization.

• Gap & Automation Identification: Proactively identify operational gaps, inefficiencies, and automation opportunities across voice AI, workflow orchestration, messaging, reporting, and tooling, translating them into actionable product work items.

• Client Engagement & Advocacy: Directly engage in client discussions, strategic partnership meetings, and product demonstrations to inform platform direction and ensure unfiltered client feedback reaches engineering.

• Cross-Functional Coordination: Drive seamless collaboration on release timelines, dependencies, testing protocols, and readiness for product launches, ensuring no critical tasks fall through the cracks.

• Market & Commercial Input: Contribute product insights to leadership discussions regarding market opportunities, competitive landscape, and product expansion strategies, informing commercial strategy.

• Process & Governance Development: Design and implement scalable product management and governance processes that support company growth while maintaining agility and speed.

📝 Enhancement Note: The responsibilities clearly indicate a need for strong operational acumen, particularly in translating complex business needs into technical requirements and vice versa. The emphasis on "operational workflows," "deployment," "implementation alignment," and "gap and automation surfacing" directly relates to the core functions of revenue and sales operations, aiming to optimize processes and drive efficiency. The role requires a deep understanding of how product features impact operational execution and client delivery.

🎓 Skills & Qualifications

Education: Bachelor's degree in Computer Science, Engineering, Business, or a related field; Master's degree or MBA preferred.

Experience: Minimum of 8 years in product strategy, product management, or product leadership roles. Demonstrated experience in successfully launching and scaling AI-driven products in regulated environments.

Required Skills:

• Product Strategy & Roadmap Development: Proven ability to define long-term product vision and translate it into actionable, multi-quarter roadmaps.

• Stakeholder Management & Communication: Exceptional ability to communicate effectively with technical (engineering, AI specialists) and non-technical (operations, sales, compliance, clients, executive leadership) stakeholders.

• Enterprise Software Implementation Support: Experience in supporting enterprise software deployments and translating operational requirements into product enhancements.

• AI & Automation Understanding: Familiarity with AI-enabled platforms, automation workflows, conversational AI, or voice technology.

• Cross-Functional Leadership: Proven track record of working effectively across engineering, operations, compliance, and executive leadership teams.

• Analytical & Problem-Solving: Strong analytical capabilities, organizational skills, and a proactive approach to problem-solving.

• Fast-Paced Environment Acumen: Ability to manage multiple competing priorities and thrive in a dynamic, high-growth environment.

• Regulated Industry Experience: Experience in or strong understanding of regulated industries such as fintech, receivables, collections, or healthcare RCM, with an emphasis on operational risk management.

Preferred Skills:

• Voice Technology & Conversational AI Expertise: In-depth knowledge of voice AI, conversational AI platforms, and their application in business processes.

• Workflow Orchestration & Messaging: Experience with workflow orchestration tools, messaging platforms, and their integration into operational systems.

• Fintech/Healthcare RCM Domain Knowledge: Deep understanding of the specific operational challenges and compliance requirements within fintech or healthcare revenue cycle management.

• Product Governance & Process Design: Experience establishing and refining product management and governance processes for scalable operations.

• LLM and Diffusion Model Familiarity: Exposure to cutting-edge AI technologies like Large Language Models (LLM) and Diffusion Models.

📝 Enhancement Note: The "8 years" requirement, coupled with the "Head of Product Strategy" title and the need to bridge business and engineering, implies a senior-level candidate who can operate strategically and tactically. The emphasis on regulated industries and operational risk management is crucial for roles supporting GTM functions in these sectors. The "AI Platform Development" and "Conversational AI" skills are highly relevant for modern GTM operations looking to leverage technology for efficiency and customer engagement.

📊 Process & Systems Portfolio Requirements

Portfolio Essentials:

• Product Strategy & Roadmap Case Studies: Showcase examples of developing and executing multi-quarter product roadmaps, highlighting the process of stakeholder alignment, prioritization, and delivery.

• Client Needs Translation Examples: Present documented instances where client needs, operational feedback, or compliance requirements were translated into clear, actionable product specifications for engineering.

• AI/Automation Initiative Demonstrations: Include case studies detailing the definition and successful implementation of AI capabilities, automation workflows, or voice technology features that improved operational efficiency or client outcomes.

• Cross-Functional Project Leadership Evidence: Provide examples of leading complex product initiatives involving engineering, operations, compliance, and sales teams, demonstrating success in coordination and problem resolution.

• Process Improvement Initiatives: Showcase projects where you identified and addressed operational gaps or inefficiencies through product enhancements, focusing on measurable improvements in key operational metrics.

Process Documentation:

• Workflow Design & Optimization: Evidence of designing or optimizing complex workflows, particularly those involving AI, automation, or customer interaction, with a focus on scalability and efficiency.

• System Implementation & Integration: Documentation demonstrating experience supporting enterprise software implementations, including the translation of operational requirements into product enhancements and managing integrations.

• Metrics & Performance Analysis: Examples of establishing feedback loops and defining metrics to measure the impact of product releases on operational performance, client satisfaction, and business objectives.

📝 Enhancement Note: For a Head of Product Strategy role with a strong operational component, a portfolio should demonstrate not just product vision but also the ability to execute that vision through robust processes and systems. This includes showing how product decisions directly impact operational efficiency, compliance, and client delivery. The candidate should be prepared to articulate the processes used to gather requirements, prioritize, and ensure successful product deployment within operational contexts.

💵 Compensation & Benefits

Salary Range: Based on industry benchmarks for a "Head of Product Strategy" role with 8+ years of experience in a high-growth tech company in Austin, TX, particularly in regulated AI/Fintech/RCM sectors, the estimated annual salary range is $180,000 - $250,000. This range accounts for base salary, potential bonuses, and stock options, reflecting the strategic importance and leadership scope of the position.

Benefits:

• Health Insurance Stipend: A monthly allowance provided to help cover the cost of an individual health insurance plan, offering flexibility in healthcare choices.

• 401k: Retirement savings plan with potential company matching, supporting long-term financial planning.

• Experienced Team Environment: Opportunity to work alongside seasoned professionals from leading tech companies, fostering mentorship and rapid skill development.

• Cutting-Edge Technology Exposure: Hands-on experience with advanced technologies such as Computer Vision, Speech Technologies, Natural Language Understanding, Generative AI, LLM, and Diffusion models.

• Rapid Career Progression: Clear pathways for professional growth and advancement, supported by senior leadership.

• Entrepreneurial Spirit: A dynamic work environment that blends the stability of large clients with the agility and innovation of a startup culture.

Working Hours: Approximately 40 hours per week, with the expectation of flexibility to meet the demands of a fast-paced, growth-oriented technology company, including occasional evening or weekend work for critical deadlines or product launches.

📝 Enhancement Note: The salary range is estimated based on industry data for senior product leadership roles in Austin, TX, considering the company's focus on AI and regulated industries. The benefits listed are directly from the job description, with added context for why they are valuable to operations professionals. The working hours are a standard estimate for full-time roles, with an acknowledgment of potential flexibility required in such positions.

🎯 Team & Company Context

🏢 Company Culture

Industry: Technology (AI, SaaS), with a strong focus on regulated sectors like Fintech, Healthcare Revenue Cycle Management (RCM), Receivables, and Collections. The company leverages AI for advanced solutions in these areas.

Company Size: Acclaim (Overtime.ai) is likely a growing mid-sized to large startup or established tech company, evidenced by its ability to attract experienced leadership and secure "big clients." This size offers a balance of structure and agility.

Founded: The company has a history of developing award-winning devices and AI products for "BigTech corporations," suggesting significant prior experience and established credibility within the industry. The "Overtime.ai" branding indicates a more recent or specific product focus.

Team Structure:

• The Product team is led by this Head of Product Strategy, who reports into executive leadership.

• Close collaboration is expected with the CTO, engineering leadership, applied AI teams, and operational departments (e.g., operations, compliance, client success, sales).

Methodology:

• Data-Driven Product Development: Emphasis on using data from client feedback, operational workflows, and market analysis to inform product decisions.

• Agile & Iterative Development: Implied by the need to manage a multi-quarter roadmap, prioritize, and adapt to fast-paced growth and AI advancements.

• Cross-Functional Collaboration: A core operating principle, bridging the gap between technical development and business/operational needs.

• Process Optimization: A continuous effort to improve product management and governance processes for scalability and efficiency.

Company Website: [Acclaim Website - Note: The provided URL is a Comeet job link, not a direct company website. A search for "Acclaim AI" or "Overtime.ai" would be needed for the actual company URL.]

📝 Enhancement Note: The company culture is characterized by a blend of advanced technological innovation (AI, LLMs) and a pragmatic, execution-focused approach, especially within regulated industries. This means a need for both visionary thinking and meticulous attention to operational detail and compliance. The "entrepreneurial spirit" alongside "secure workspace thanks to big clients" suggests a stable yet innovative environment.

📈 Career & Growth Analysis

Operations Career Level: This is a senior leadership role, specifically a "Head of" position, indicating significant responsibility and strategic influence. It sits at the executive or near-executive level, managing a critical function that directly impacts the company's product direction and operational scalability.

Reporting Structure: The Head of Product Strategy will likely report directly to a C-suite executive, such as the CEO, CTO, or Chief Product Officer, depending on the company's organizational structure. They will lead a team of product managers and work collaboratively with other department heads.

Operations Impact: This role is pivotal in ensuring that the company's product strategy directly supports and enables efficient, scalable operations and Go-To-Market (GTM) execution. By defining the roadmap and bridging technical and operational needs, the Head of Product Strategy directly influences revenue generation, client satisfaction, and compliance adherence.

Growth Opportunities:

• Strategic Leadership Expansion: Potential to expand leadership scope, potentially overseeing a larger product organization or taking on broader strategic responsibilities within the company.

• Domain Specialization: Deepen expertise in AI applications within regulated industries (Fintech, RCM), becoming a recognized leader in this niche.

• Influence on Company Direction: Play a key role in shaping the company's long-term vision and market positioning through product innovation.

• Mentorship & Team Building: Opportunity to build and mentor a high-performing product team, fostering a culture of innovation and operational excellence.

• Advanced Technology Immersion: Continuous learning and application of cutting-edge AI technologies, staying at the forefront of industry advancements.

📝 Enhancement Note: The "Head of" title signifies a leadership track position. The emphasis on bridging operational needs with product development suggests significant growth potential for individuals who can demonstrably drive efficiency and scalability through product strategy, a key metric for GTM and revenue operations leaders.

🌐 Work Environment

Office Type: The role is specified as "On-site" in Austin, Texas. This suggests a traditional office-based work environment, fostering in-person collaboration and team cohesion.

Office Location(s): Austin, Texas. This location is a major tech hub, offering access to talent and a vibrant ecosystem. Specific office details would be available upon inquiry.

Workspace Context:

• Collaborative Hub: The office environment is likely designed to facilitate close collaboration between product, engineering, operations, and other cross-functional teams, with ample meeting spaces and open-plan areas.

• Technology Enabled: Access to modern office technology, robust IT infrastructure, and potentially specialized equipment for AI/tech development.

• Dynamic Atmosphere: Given the company's entrepreneurial spirit and focus on cutting-edge technology, the workspace is expected to be dynamic, fast-paced, and conducive to innovation.

Work Schedule: While the standard is around 40 hours per week, the on-site nature and the demands of a leadership role in a fast-growing tech company imply a need for flexibility. This role will require significant dedication to ensure product launches, operational alignment, and stakeholder communication are managed effectively, potentially involving extended hours during critical periods.

📝 Enhancement Note: The "On-site" requirement in Austin indicates a preference for in-person collaboration, which is often beneficial for roles requiring complex cross-functional alignment and rapid problem-solving, common in GTM and operations. This environment can foster stronger team dynamics and knowledge sharing.

📄 Application & Portfolio Review Process

Interview Process:

• Initial Screening: A review of your resume and portfolio by a recruiter or hiring manager to assess alignment with the core requirements and experience level.

• Hiring Manager Interview: In-depth discussion with the hiring manager (likely a senior executive) focusing on product strategy philosophy, leadership experience, and understanding of AI and regulated industries.

• Cross-Functional Interviews: Meetings with key stakeholders from engineering, operations, compliance, and potentially client success/sales to assess collaboration skills, communication style, and ability to translate needs across departments.

• Product Strategy Case Study/Presentation: A common element for senior product roles. Candidates will likely be asked to present a strategic product initiative, roadmap proposal, or solution to a hypothetical business challenge, demonstrating their analytical, strategic, and presentation skills. This is where portfolio examples will be critical.

• Executive Review: Final interviews with C-suite executives to evaluate overall fit, strategic vision, and leadership potential.

Portfolio Review Tips:

• Highlight Operations Impact: For each portfolio item, clearly articulate how the product initiative influenced or improved operational efficiency, scalability, compliance, or GTM effectiveness. Use specific metrics.

• Showcase Process & Methodology: Detail the product development process, stakeholder engagement, and prioritization frameworks used. Emphasize how you managed trade-offs and resolved conflicts.

• Quantify Results: Wherever possible, use data and metrics to demonstrate the tangible outcomes of your product strategies and implementations (e.g., reduced cycle times, increased conversion rates, improved compliance scores).

• Structure for Clarity: Organize your portfolio logically, perhaps by product type, initiative, or impact area. Use clear headings, concise descriptions, and compelling visuals (if applicable).

• Tailor to Acclaim: Research Acclaim/Overtime.ai's specific challenges and market position. Frame your portfolio examples to show how your experience is directly relevant to their needs, especially concerning AI in regulated industries.

Challenge Preparation:

• Operational Bottleneck Analysis: Be prepared to analyze a hypothetical operational bottleneck within a fintech or RCM context and propose product-led solutions.

• Roadmap Prioritization Scenarios: Practice articulating how you would prioritize competing roadmap requests from different stakeholders (e.g., sales vs. compliance vs. engineering).

• AI Integration Strategy: Think about how you would define requirements for integrating a new AI capability (e.g., LLM for customer support) into an existing operational workflow.

• Communication & Influence: Prepare examples of how you have influenced senior leadership or cross-functional teams to adopt your product strategy recommendations.

📝 Enhancement Note: The interview process for a Head of Product Strategy role is rigorous, focusing on strategic thinking, leadership, and practical execution. A strong portfolio is essential, particularly one that highlights experience in translating business needs into product solutions that drive operational efficiency and scalability. The emphasis on regulated industries and AI means candidates should be ready to discuss these specific areas in depth.

🛠 Tools & Technology Stack

Primary Tools:

• Product Management Platforms: Jira, Confluence, Asana, Aha!, Productboard, or similar for roadmap planning, backlog management, and documentation.

• Collaboration & Communication: Slack, Microsoft Teams for real-time communication and team collaboration.

• CRM: Salesforce, HubSpot, or similar, to understand client interactions and sales pipelines.

• Analytics & BI Tools: Tableau, Power BI, Looker, or internal proprietary tools for data analysis and reporting.

• AI/ML Development Tools: Familiarity with platforms and tools used in AI development, even if not directly hands-on. This could include cloud ML platforms (AWS SageMaker, Google AI Platform, Azure ML), data science notebooks (Jupyter), and MLOps tools.

Analytics & Reporting:

• Data Warehousing/Lakes: Knowledge of how data is stored and accessed for analysis (e.g., Snowflake, Redshift, BigQuery).

• SQL: Proficiency in querying databases to extract and analyze data.

• Reporting Dashboards: Experience creating and interpreting dashboards to track product performance, operational metrics, and business KPIs.

CRM & Automation:

• Workflow Automation Tools: Understanding of tools that automate business processes, potentially including CRM automation features or dedicated workflow engines.

• Integration Platforms: Familiarity with how different systems connect (e.g., Zapier, MuleSoft, custom APIs) to ensure seamless data flow between product, operations, and other business systems.

📝 Enhancement Note: While this role is strategic, a strong understanding of the technology stack used by product, engineering, and operations teams is crucial for effective collaboration and decision-making. The emphasis on AI and regulated industries means familiarity with relevant tools and platforms in these domains is a significant advantage.

👥 Team Culture & Values

Operations Values:

• Data-Driven Decision Making: A strong emphasis on using data and analytics to inform product strategy, prioritize initiatives, and measure success. Operations professionals are expected to be analytical and evidence-based.

• Efficiency & Scalability: A core focus on optimizing processes and building products that can scale to meet growing business demands and client needs without compromising quality or compliance.

• Cross-Functional Collaboration: A culture that values open communication and teamwork across departments, recognizing that product success is a shared responsibility.

• Client Focus: A commitment to understanding and meeting client needs, ensuring that product development directly contributes to client value and satisfaction.

• Innovation & Continuous Improvement: Encouraging exploration of new technologies (e.g., AI) and a mindset of constantly seeking ways to improve products, processes, and outcomes.

Collaboration Style:

• Partnership-Oriented: The Head of Product Strategy acts as a partner to engineering, operations, compliance, and sales, working collaboratively to achieve shared objectives.

• Transparent Communication: Open and honest dialogue is encouraged, with a focus on clearly articulating priorities, trade-offs, and potential challenges.

• Feedback-Rich Environment: A culture where constructive feedback is welcomed and utilized for continuous improvement of both products and processes.

• Agile & Responsive: The team is expected to be adaptable and responsive to market changes, client feedback, and evolving technological capabilities.

📝 Enhancement Note: The company values likely reflect a blend of innovation and execution, essential for a company operating in AI and regulated industries. For operations professionals, understanding these values is key to demonstrating cultural fit and alignment with the company's strategic direction.

⚡ Challenges & Growth Opportunities

Challenges:

• Balancing Long-Term Vision with Short-Term Needs: Effectively managing the inherent tension between strategic platform development and immediate operational requirements and client requests.

• Navigating Complex Regulatory Landscapes: Ensuring product strategy and development adhere to stringent compliance requirements within industries like fintech and healthcare RCM.

• Integrating Evolving AI Technologies: Staying ahead of rapid advancements in AI and effectively incorporating new capabilities into the product roadmap in a scalable and responsible manner.

• Driving Cross-Functional Alignment: Achieving consensus and coordinated action among diverse teams (engineering, operations, sales, compliance) with potentially competing priorities.

• Scaling Processes: Developing and implementing product management processes that can effectively support rapid company growth without hindering agility.

Learning & Development Opportunities:

• Advanced AI & ML Training: Opportunities to deepen understanding and application of cutting-edge AI technologies relevant to product development.

• Industry-Specific Knowledge: Gaining in-depth expertise in the intricacies of fintech, RCM, and other regulated sectors.

• Leadership Development Programs: Access to training and mentorship focused on enhancing strategic leadership, team management, and executive communication skills.

• Conferences & Industry Events: Potential to attend relevant industry conferences to stay abreast of market trends, network with peers, and represent the company.

• Strategic Impact: The opportunity to significantly influence the trajectory of a growing technology company by shaping its core product offerings.

📝 Enhancement Note: These challenges and opportunities are common for senior product leadership roles in innovative tech companies, especially those operating in complex, regulated environments. The role offers significant potential for growth by tackling these challenges and leveraging the associated learning opportunities.

💡 Interview Preparation

Strategy Questions:

• "Describe your process for developing and prioritizing a multi-quarter product roadmap. How do you balance strategic vision with immediate operational needs?" (Focus on your structured approach, stakeholder management, and trade-off decision-making.)

• "How would you translate a complex compliance requirement in the fintech/RCM space into actionable product specifications for an engineering team?" (Demonstrate your understanding of both regulatory nuances and technical translation.)

Company & Culture Questions:

• "What do you see as the biggest opportunities and challenges for AI adoption in regulated industries like fintech and healthcare RCM?" (Research industry trends and demonstrate strategic foresight.)

• "How would you foster collaboration between product, engineering, and operations to ensure successful product launches and operational scalability?" (Highlight your experience with cross-functional leadership and communication.)

Portfolio Presentation Strategy:

• The "Why, What, How, and Impact" Framework: For each case study, clearly articulate:

  • Why: The problem or opportunity addressed.
  • What: The product solution developed.
  • How: The process of development, prioritization, and collaboration (including overcoming challenges).
  • Impact: The measurable results achieved (e.g., increased efficiency, revenue growth, cost savings, improved compliance).

• Focus on Operational Relevance: Explicitly connect your product initiatives to improvements in operational workflows, scalability, and GTM effectiveness.

• Concise & Data-Rich: Keep descriptions brief and impactful, backing up claims with specific data points and metrics.

• Engage Your Audience: Be prepared to discuss your work in detail, answer questions thoughtfully, and adapt your presentation based on interviewer interest.

📝 Enhancement Note: Preparing for these types of questions involves not only understanding product strategy but also demonstrating a deep appreciation for operational realities, regulatory constraints, and the practical application of AI. Your portfolio should serve as concrete evidence for your responses.

📌 Application Steps

To apply for this Head of Product Strategy position:

• Submit your application: Use the provided link on Comeet. Ensure your application is complete and accurate.

• Tailor your Resume: Highlight experience in product strategy, product management, AI platforms, regulated industries (Fintech, RCM), and cross-functional leadership. Quantify achievements with specific metrics.

• Prepare your Portfolio: Curate 2-3 key projects that best demonstrate your ability to develop product strategy, translate operational needs into product specifications, and drive measurable business impact. Focus on AI, regulated industries, and operational efficiency.

• Research Acclaim/Overtime.ai: Understand their mission, products, target markets, and any recent news. Identify how your skills and experience align with their specific challenges and growth opportunities.

• Practice your "Story": Be ready to articulate your career journey, your product philosophy, and why you are the ideal candidate for this specific role, emphasizing your operational perspective.

⚠️ 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.