Technical AI Program Manager, Product Strategy & Operations (Hybrid/Remote)

📍 Job Overview

Job Title: Technical AI Program Manager, Product Strategy & Operations (Hybrid/Remote)

Company: Reap

Location: Hong Kong, Singapore, Malaysia, Taiwan

Job Type: Full-time

Category: Product Operations / Strategy & Operations

Date Posted: 2026-06-24

Experience Level: 5+ Years

Remote Status: Hybrid/Remote

🚀 Role Summary

• Spearhead the design and implementation of a robust operating model for Product, Engineering, and Design functions, focusing on enhancing shipping velocity and consistency.

• Drive critical, high-stakes initiatives that span multiple departments including Product, Engineering, Commercial, and Legal, ensuring seamless cross-functional execution.

• Leverage Artificial Intelligence (AI) tools extensively to automate manual tasks, improve decision-making quality, and accelerate overall execution within the organization.

• Develop and manage key business rhythms and communication cadences for Product leadership, ensuring actionable metrics and clear ownership for follow-up actions.

📝 Enhancement Note: This role is positioned as a strategic operator, not a project coordinator. The primary focus is on shaping the how of product development and delivery, emphasizing process design, operational discipline, and the strategic application of AI to enhance organizational efficiency and throughput. The emphasis on "AI-native" and active AI tool usage is a critical differentiator.

📈 Primary Responsibilities

• Planning Cycles: Lead quarterly and annual planning processes for all product divisions, translating leadership priorities into scoped initiatives with defined owners, clear milestones, and measurable outcomes.

• Operating Model Design: Architect and maintain the operational framework for Product, Engineering, and Design, encompassing rituals, planning cadences, decision-making frameworks, intake processes, prioritization mechanisms, and role clarity across functions.

• Delivery Frameworks: Collaborate with leads in Product, Engineering, Commercial, and Legal to establish and operationalize engagement criteria, handoff protocols, and role definitions, ensuring teams understand their responsibilities and project transition points.

• Business Rhythms: Build and manage weekly, monthly, and quarterly cadences for Product leadership, ensuring metrics are defined, actionable, and directly linked to owners and subsequent actions.

• Cross-Functional Execution: Take ownership of the highest-priority, cross-functional initiatives, actively unblocking teams, escalating issues when necessary, and driving them to successful completion.

• Communication Strategy: Define and manage internal communication strategies for the organization's work, ensuring effective information flow upwards to leadership, laterally across departments, and broadly to the entire company.

• AI-Powered Operations: Proactively identify opportunities for AI to reduce manual effort, elevate decision quality, or accelerate execution; build, commission, or integrate AI tools and workflows, and ensure responsible governance as these assets scale.

📝 Enhancement Note: The responsibilities highlight a blend of strategic operational design and hands-on execution, with a strong emphasis on process ownership and AI integration. The "What You'll Own" section clearly defines the scope of impact, focusing on system-level improvements rather than individual project delivery.

🎓 Skills & Qualifications

Education:

• While no specific degree is mandated, a Bachelor's or Master's degree in a relevant field such as Business Administration, Operations Management, Computer Science, or a related discipline is often preferred for roles of this strategic and technical nature. Experience:

• 5+ years of progressive experience in program management, chief of staff roles, solutions operations, or a similar embedded operating function within a product or engineering organization.

• Demonstrated track record of independently owning and designing an operating model, rather than solely managing project execution.

• Proven ability to seamlessly transition between strategic thinking and tactical execution, including defining frameworks, drafting narratives, establishing cadences, aligning stakeholders, and meticulously managing details.

• Comfort operating within technical environments, effectively collaborating with engineers and product managers without necessarily being a hands-on coder.

• Experience building or scaling reporting mechanisms, operational cadences, backlog management systems, or cross-functional workflow systems.

• Strong judgment regarding governance and risk management, particularly concerning the responsible scaling of new tools, AI workflows, or shared organizational assets. Required Skills:

• Program Management: Expertise in overseeing complex, cross-functional programs from inception to completion.

• Operating Model Design: Ability to architect, document, and implement effective operational frameworks for product and engineering teams.

• AI Tool Integration & Application: Proven experience and active, daily use of AI tools (e.g., Claude, ChatGPT, Notion AI) for synthesis, drafting, analysis, and workflow design.

• Product Strategy Acumen: Understanding of product development lifecycles and the strategic considerations that drive product success.

• Cross-functional Execution: Skill in driving initiatives across diverse departments (Product, Engineering, Commercial, Legal) and resolving complex interdependencies.

• Stakeholder Alignment & Communication: Exceptional ability to communicate complex technical and operational concepts clearly to both technical and non-technical audiences, ensuring alignment across all levels.

• Backlog Management & Prioritization: Proficiency in managing product backlogs, defining scope, and establishing effective prioritization frameworks.

• Workflow Automation: Experience in identifying and implementing automation opportunities to improve efficiency and reduce manual work.

• Strategic Planning: Capability to lead and contribute to quarterly and annual planning cycles.

• Business Operations: Deep understanding of operational best practices within a technology-driven company.

• Technical Communication: Ability to translate between technical teams and business stakeholders.

• Governance and Risk Management: Strong judgment in establishing and enforcing controls for new technologies and processes.

Preferred Skills:

• Experience in a scaling B2B FinTech or infrastructure company.

• Previous consulting experience in operating model design, cross-functional problem-solving, or complex program delivery.

• Familiarity with card issuing, payments, or stablecoin products.

• Experience building internal AI tools, automations, or reusable assets that demonstrably reduced repetitive work across a team.

📝 Enhancement Note: The emphasis on "actively uses AI tools" is a critical requirement, suggesting the role is not just about managing operations but also about leveraging cutting-edge technology to redefine them. The distinction between "program management" and "operating model design" is key, highlighting a strategic, system-level focus.

📊 Process & Systems Portfolio Requirements

Portfolio Essentials:

• Demonstrate a portfolio showcasing successful design and implementation of operational frameworks or operating models for product, engineering, or cross-functional teams.

• Include case studies that highlight your ability to drive complex, cross-functional initiatives, detailing the challenges, your approach, and the measurable outcomes achieved.

• Present examples of how you have identified and implemented process improvements or automation, ideally showcasing the use of AI tools or technologies to enhance efficiency.

• Showcase your capabilities in establishing and managing business rhythms, planning cycles, and communication cadences, with clear examples of metrics tracked and actions taken. Process Documentation:

• Provide evidence of designing and documenting workflows, decision frameworks, and role clarity across different teams or departments.

• Exhibit documentation for operating cadences, including meeting structures, agenda templates, and follow-up mechanisms designed to drive accountability.

• Showcase examples of how you've managed and evolved backlogs or initiative tracking systems, ensuring visibility and progress tracking.

• Include documentation related to governance or risk management protocols established for new processes or technology implementations.

📝 Enhancement Note: For a role focused on operating model design and AI integration, candidates should be prepared to present tangible examples of systems they've built or significantly improved. This includes not just project management but the architecture of how teams operate, with a strong emphasis on quantifiable improvements and the strategic application of AI.

💵 Compensation & Benefits

Salary Range:

• Given the strategic nature of the role, the required experience level (5+ years), the focus on AI and FinTech, and the global hiring locations (Hong Kong, Singapore, Malaysia, Taiwan), a competitive salary range is expected.

• For a Technical AI Program Manager, Product Strategy & Operations with 5-10 years of experience in these regions, typical annual base salaries could range from USD $100,000 to $180,000, depending on the specific location, candidate experience, and negotiation.

  • Hong Kong: Likely at the higher end due to cost of living and FinTech hub status.
  • Singapore: Also competitive, similar to Hong Kong.
  • Malaysia: Potentially lower end, but still significant for a senior role.
  • Taiwan: Competitive, with variations based on experience.

• This estimate assumes a base salary and does not include potential bonuses, stock options, or other benefits. Benefits:

• Insurance Coverage: Comprehensive health and potentially other insurance benefits provided after the probation period.

• Reap Card Stipend: A specific benefit related to the company's core product, likely offering a credit or allowance for using Reap's corporate card services.

• AI Tools Access & Development: Significant emphasis on providing access to and opportunities to learn/experiment with AI tools, reflecting the company's AI-native culture.

• Flexible Hybrid/Remote Work Environment: Allows for work-life balance and accommodates employees across different geographies.

• Global, Collaborative Team: Opportunity to work with a diverse, international team.

• Culture of Innovation, Inclusion, and Continuous Learning: An environment that supports professional development and forward-thinking practices.

Working Hours:

• While the standard for full-time employment is typically 40 hours per week, the hybrid/remote nature and global team structure suggest flexibility might be a key aspect. However, the demands of managing planning cycles, business rhythms, and cross-functional execution may require significant dedication and adaptive scheduling to accommodate different time zones and critical deadlines.

📝 Enhancement Note: Salary ranges are estimates based on industry benchmarks for similar roles in FinTech and Operations in the specified regions. Actual compensation will vary based on the candidate's qualifications, negotiation, and the specific compensation strategy of Reap for each location. The benefits package strongly emphasizes the company's core offerings and its AI-centric approach.

🎯 Team & Company Context

🏢 Company Culture

Industry: Financial Technology (FinTech), specifically focusing on stablecoin-enabled payments, corporate cards, and financial infrastructure.

Company Size: While not explicitly stated, "growing fast across multiple product lines" and "employees across multiple countries" suggests a scaling startup or scale-up phase, likely in the range of 100-500 employees. This size implies a dynamic environment with opportunities for significant impact but also a need for structured operations to manage growth.

Founded: Not specified, but the description implies a relatively recent founding, given the focus on building new infrastructure and leveraging emerging technologies like stablecoins and AI.

Team Structure:

• The role is embedded within the "Product, Engineering & Design organisation," acting as a primary partner to the Head of Product. This indicates a close working relationship with product leadership and a significant influence on how these core technical and creative teams operate.

• The role will report to product leadership but will work extensively with leads across Product, Engineering, Commercial, and Legal, highlighting a matrixed or highly collaborative reporting structure for initiatives.

• The emphasis is on fostering a disciplined operating model that improves collaboration and consistency across these functions. Methodology:

• Data Analysis & Insights: The role requires driving decisions based on actionable metrics and data, particularly within business rhythms and planning cycles.

• Workflow Planning & Optimization: A core function is designing and maintaining how teams work, focusing on efficiency, clarity, and speed.

• Automation & Efficiency: Proactive identification and implementation of AI-powered solutions to eliminate manual work and accelerate execution are central to the role's methodology.

Company Website: https://careers.reap.global

📝 Enhancement Note: Reap positions itself as an innovative FinTech company building foundational infrastructure. The culture is described as AI-native, innovative, inclusive, and focused on continuous learning. The company size and growth stage suggest an environment where operational processes are being actively shaped, making this role critical for establishing scalable practices.

📈 Career & Growth Analysis

Operations Career Level: This role is a senior-level individual contributor position, often referred to as a "strategic operator" or "technical program manager" with a strong operations focus. It sits at the intersection of product strategy, engineering operations, and business operations, requiring a blend of strategic vision and tactical execution. It's a role that can lead to further specialization in operations leadership, product operations, or even Chief of Staff roles.

Reporting Structure: The role is a primary partner to the Head of Product, Product, Engineering & Design. While reporting into product leadership, it requires extensive collaboration and influence across Engineering, Commercial, and Legal departments.

Operations Impact: The role is designed to have a direct and significant impact on the organization's ability to deliver products and features efficiently and consistently. By optimizing the operating model and leveraging AI, it aims to accelerate revenue-generating product development, improve time-to-market for new FinTech solutions, and enhance overall operational scalability.

Growth Opportunities:

• Operations Specialization: Deepen expertise in designing and scaling operating models for high-growth tech companies, particularly in FinTech.

• AI Strategy & Implementation: Become a leader in leveraging AI for operational efficiency, potentially moving into roles focused on AI product management or operational AI strategy.

• Leadership & Chief of Staff Path: Develop skills and visibility that could lead to a Chief of Staff role, or management positions within operations, product operations, or program management.

• Industry Expertise: Gain significant experience in the rapidly evolving stablecoin and borderless payments space, becoming a subject matter expert in FinTech operations.

• Mentorship & Team Building: As Reap scales, there will be opportunities to build and mentor teams focused on operational excellence and AI integration.

📝 Enhancement Note: This role is ideal for an operations professional who thrives on building systems, optimizing processes, and is at the forefront of adopting new technologies like AI. The growth potential is significant, offering a pathway into leadership and specialized operational roles within a high-growth FinTech environment.

🌐 Work Environment

Office Type: The company offers a "Flexible hybrid/remote work environment." This typically means employees can choose to work from home, an office (if available and desired), or a combination of both, depending on team needs and individual preference. The presence of multiple international locations suggests a distributed workforce model.

Office Location(s): The role is open to candidates in Hong Kong (Quarry Bay), Singapore, Malaysia, and Taiwan. This distributed nature requires strong asynchronous communication skills and a robust digital collaboration infrastructure.

Workspace Context:

• Collaborative Environment: Despite the remote/hybrid nature, the emphasis on cross-functional execution and communication suggests a highly collaborative digital workspace. Tools for real-time and asynchronous communication will be essential.

• Operations Tools & Technology: The role will heavily involve leveraging and potentially implementing various operations, project management, and AI tools. Access to robust technology infrastructure is implied.

• Team Interaction: Opportunities for interaction will be through structured meetings (virtual), collaborative platforms, and potentially in-person meetups or offsites if company policy allows.

Work Schedule:

• The role is full-time, typically requiring 40 hours per week. However, due to the global distribution of teams and the nature of managing cross-functional initiatives and business rhythms, flexibility in working hours will be necessary to accommodate different time zones and ensure continuous progress. Successful candidates will need to be adept at managing their schedules to meet deadlines and participate in critical meetings across regions.

📝 Enhancement Note: The hybrid/remote aspect is a key feature, appealing to candidates seeking flexibility. However, the "Technical AI Program Manager" title and responsibilities suggest a demanding role that requires proactive engagement and excellent self-management skills, especially in a distributed team setting.

📄 Application & Portfolio Review Process

Interview Process:

• Initial Screening: A review of your application and resume to assess alignment with the experience and skills required, particularly the 5+ years in operations/program management and active AI tool usage.

• Hiring Manager/Team Interview: Typically involves a discussion with the hiring manager (e.g., Head of Product) and potentially other key stakeholders. Expect questions focused on your experience designing operating models, managing complex programs, and your approach to AI integration.

• Case Study/Practical Exercise: A common step for such roles. You might be asked to analyze a hypothetical operational challenge, propose an operating model for a new feature launch, or outline an AI automation strategy. This assesses your problem-solving, strategic thinking, and communication skills.

• Cross-functional Interviews: Discussions with leads from Engineering, Commercial, or Legal to assess your ability to collaborate and communicate effectively across different departments.

• Final Interview: Potentially with senior leadership to discuss strategic alignment, cultural fit, and overall impact potential.

Portfolio Review Tips:

• Quantify Impact: For each project or initiative presented, clearly articulate the problem statement, your specific role and actions, the solutions implemented (especially AI-driven ones), and the measurable results (e.g., % increase in shipping speed, % reduction in manual effort, improvement in consistency metrics).

• Showcase Operating Model Design: If you have designed an operating model, present its key components: planning cadences, decision frameworks, intake processes, communication flows, and how it improved team performance.

• Demonstrate AI Proficiency: Highlight specific instances where you actively used AI tools (Claude, ChatGPT, Notion AI, etc.) to achieve outcomes. This could include drafting proposals, analyzing data, generating first drafts of documentation, or designing workflows. Be ready to explain how you used them and the benefits derived.

• Structure for Clarity: Organize your portfolio logically, perhaps by functional area (e.g., Planning, Operating Model, Cross-functional Execution) or by project. Use clear headings, concise descriptions, and visual aids where appropriate.

• Tailor to the Role: Emphasize aspects of your experience that directly align with Reap's needs: scaling operations, AI integration, FinTech environment, and cross-functional collaboration.

Challenge Preparation:

• Operating Model Design: Be prepared to discuss how you would design or refine an operating model for a growing Product, Engineering, and Design team, considering their specific challenges.

• AI Strategy: Think about how you would identify opportunities for AI in operations, assess potential tools, manage risks, and implement them effectively within an organization.

• Cross-functional Problem Solving: Prepare examples of how you've navigated complex interdependencies and unblocked teams in previous roles.

• Metrics & Reporting: Consider how you would define key operating metrics and build reporting cadences for leadership.

📝 Enhancement Note: The emphasis on portfolio presentation and practical challenges is crucial. Candidates must be ready to demonstrate their strategic thinking, operational design capabilities, and their practical application of AI tools in a business context, rather than just discussing theoretical knowledge.

🛠 Tools & Technology Stack

Primary Tools:

• Project & Program Management: Jira, Asana, Trello, Monday.com, or similar for backlog management, task tracking, and workflow visualization.

• AI Tools: Active and proficient daily use of Large Language Models (LLMs) such as Claude, ChatGPT, Notion AI, or similar for synthesis, drafting, analysis, and workflow design.

• Collaboration Platforms: Slack, Microsoft Teams for real-time communication and team interaction.

• Documentation & Knowledge Management: Notion, Confluence, Google Workspace (Docs, Sheets, Slides) for documentation, process design, and communication.

Analytics & Reporting:

• BI Tools: Tableau, Power BI, Looker, or similar for creating dashboards and analyzing operational metrics.

• Data Analysis: Proficiency in using spreadsheets (Excel, Google Sheets) and potentially SQL or basic data analysis techniques to interpret data and generate insights.

• Reporting Dashboards: Experience building and maintaining dashboards that track key performance indicators (KPIs) for product development and operations.

CRM & Automation:

• CRM Systems: Salesforce, HubSpot, or similar (though less directly relevant unless integrating with sales/commercial operations).

• Automation Tools: While the role focuses on AI for automation, experience with general workflow automation tools (e.g., Zapier, Make) could be beneficial.

• Integration Tools: Understanding of how different systems connect and data flows between them.

📝 Enhancement Note: The explicit mention of AI tools like Claude, ChatGPT, and Notion AI as core to daily work is a significant indicator of the technology stack and required skills. Candidates should be prepared to discuss their specific experience and proficiency with these and related productivity and operational management tools.

👥 Team Culture & Values

Operations Values:

• Innovation & AI-Native: A core value is embracing and actively leveraging AI to drive efficiency and redefine operational practices. This means a willingness to experiment, learn, and implement new AI-driven solutions.

• Efficiency & Speed: The company aims to ship more, faster, with greater consistency. This implies a culture that values streamlined processes, proactive problem-solving, and a bias for action.

• Collaboration & Cross-Functional Partnership: Success depends on effective teamwork across Product, Engineering, Commercial, and Legal. A culture of open communication, mutual respect, and shared ownership is essential.

• Discipline & Rigor: While fast-paced, the operations model must be disciplined, with clear frameworks, processes, and accountability to ensure consistency and quality.

• Continuous Learning: The rapidly evolving nature of FinTech and AI necessitates a culture where continuous learning, skill development, and adaptation are encouraged and supported.

Collaboration Style:

• Proactive & Outcome-Oriented: Collaboration is driven by a focus on achieving specific, measurable outcomes and proactively unblocking progress.

• Transparent & Communicative: Open sharing of information, progress, and challenges is expected, facilitated by robust communication tools and cadences.

• Data-Informed: Decisions and collaborations are expected to be informed by data and operational metrics.

• Constructive Feedback: A culture that encourages providing and receiving constructive feedback to continuously improve processes and collaboration.

📝 Enhancement Note: The strong emphasis on AI, efficiency, and cross-functional collaboration defines the core cultural drivers for this role. Candidates should demonstrate how their values and working style align with these principles.

⚡ Challenges & Growth Opportunities

Challenges:

• Scaling Operations in a Rapidly Growing Company: Implementing and refining operating models that can keep pace with rapid growth without becoming overly bureaucratic.

• Integrating AI Responsibly: Identifying the right AI tools, managing risks associated with AI implementation (e.g., data privacy, bias, accuracy), and ensuring their effective adoption across teams.

• Driving Change Management: Influencing stakeholders and teams to adopt new processes, tools, and ways of working, especially those powered by AI.

• Balancing Speed and Quality: Ensuring that the drive for faster execution doesn't compromise the quality, consistency, or governance of product delivery.

• Managing Distributed Teams: Effectively collaborating and driving execution across multiple time zones and geographic locations.

Learning & Development Opportunities:

• Deep Dive into AI for Operations: Become an expert in applying cutting-edge AI tools and techniques to optimize business processes, product development, and strategic planning.

• FinTech & Stablecoin Expertise: Gain in-depth knowledge of the financial technology sector, particularly in areas like stablecoin payments and corporate card issuance.

• Operating Model Design Mastery: Develop advanced skills in architecting and implementing scalable operating models for tech organizations.

• Strategic Program Leadership: Grow into a leadership role, potentially managing larger programs, a team of program managers, or moving into a Chief of Staff capacity.

• Industry Conferences & Certifications: Opportunities to attend relevant industry events and pursue certifications related to AI, program management, or FinTech.

📝 Enhancement Note: The challenges presented are typical for a fast-scaling tech company leveraging new technologies. The growth opportunities are substantial, particularly for those interested in the intersection of AI, FinTech, and operational excellence.

💡 Interview Preparation

Strategy Questions:

• "Describe a time you designed and implemented an operating model for a product or engineering team. What were the key components, and what was the impact?" (Focus on your process, specific frameworks, and quantifiable results.)

• "How do you identify opportunities for AI to improve operational efficiency? Walk us through your process for evaluating, implementing, and governing AI tools." (Be ready to cite specific AI tools you use and examples of how they've solved problems.)

• "Imagine you need to launch a critical new feature that requires coordination between Product, Engineering, Commercial, and Legal. How would you structure the planning, execution, and communication for this initiative?" (Highlight your approach to cross-functional alignment, risk management, and progress tracking.) Company & Culture Questions:

• "Reap is an AI-native company. How do you see AI transforming product operations, and how have you personally leveraged AI to achieve significant results in your previous roles?" (Be enthusiastic about AI and provide concrete examples.)

• "How would you approach building business rhythms and communication cadences for a fast-growing Product leadership team?" (Discuss your philosophy on meetings, reporting, and accountability.)

• "Describe a situation where you had to influence stakeholders across different departments to adopt a new process or technology. What was your strategy, and what was the outcome?" (Showcase your communication and change management skills.) Portfolio Presentation Strategy:

• The STAR Method (Situation, Task, Action, Result): Structure your case studies using this framework to provide clear, concise, and impactful stories.

• Quantify Everything: For each example, aim to include specific metrics: percentage improvements, time saved, reduction in errors, increase in throughput, etc.

• Show, Don't Just Tell: If possible, use visuals (diagrams of workflows, dashboard examples, process maps) to illustrate your points.

• Focus on AI Application: Clearly articulate how AI was used in your examples and what benefits it brought. This is a critical differentiator for this role.

• Tailor to Reap: Research Reap's products and mission. Try to frame your examples in a way that aligns with their FinTech focus and their need for scalable operational infrastructure.

📝 Enhancement Note: Interview preparation should heavily emphasize practical experience with AI tools and operating model design. Candidates should be ready to articulate their strategic thinking, problem-solving abilities, and their capacity to drive change within a dynamic, technology-forward organization.

📌 Application Steps

To apply for this operations position:

• Submit your application through the application link provided on the Reap careers page.

• Portfolio Customization: Prepare a portfolio or a detailed document that highlights 2-3 key projects demonstrating your experience in operating model design, cross-functional program management, and significant AI tool application. Focus on projects where you achieved measurable efficiency gains or improved team output.

• Resume Optimization: Tailor your resume to emphasize keywords from the job description, such as "Program Management," "Operating Model Design," "AI Tools," "Product Strategy," "Cross-functional Execution," and "FinTech." Quantify your achievements wherever possible.

• Interview Preparation: Practice articulating your experience using the STAR method, focusing on strategic thinking, operational design, and AI integration. Be ready to discuss specific AI tools you've used and their impact.

• Company Research: Thoroughly research Reap's mission, products (stablecoins, corporate cards, APIs), and recent news. Understand their position in the FinTech market and be prepared to discuss how your role contributes to their strategic goals.

⚠️ 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.