Chief of Staff

About The Role

As Chief of Staff to the CEO, you will amplify the effectiveness of the CEO and Executive Team by creating clarity around priorities, strengthening cross-functional alignment, and ensuring that the company’s most important initiatives move from strategy to execution.

Working closely with the CEO and leaders across Product, Engineering, Operations, Finance, Commercial, Legal, and People, you will serve as a trusted thought partner and hands-on operator. You will help frame strategic questions, improve decision quality, maintain the operating rhythm of the business, lead CEO-sponsored initiatives, and support investor and board engagement.

This role is suited to someone who is comfortable operating in ambiguity, can move fluidly between strategic analysis and execution, and has the judgment and influence to drive outcomes across senior stakeholders without relying on formal authority.

What You Will Do

Partner with the CEO on Strategy and Decision-Making

You will help the CEO and Executive Team bring structure to complex questions, clarify priorities, and make well-informed decisions using data, business context, and cross-functional input.

You Will:

• Frame strategic questions, assess trade-offs, and synthesize inputs from across the organization.
• Prepare executive briefs, decision memos, presentations, and strategic analyses.
• Translate complex information into clear recommendations and decision points.
• Help maintain focus on the priorities that matter most to the business.
  
  

Drive Company Priorities From Strategy To Execution

You will turn strategic priorities into executable plans and operating cadences, creating visibility, accountability, and follow-through across the organization.

You Will:

• Translate company strategy into plans, milestones, OKRs, and quarterly priorities.
• Facilitate executive reviews, planning sessions, and follow-ups.
• Track progress, surface risks and dependencies, and drive corrective action when needed.
• Strengthen ownership and execution discipline across company-wide priorities.
  
  

Lead Cross-Functional Strategic Initiatives

You will own selected CEO-sponsored initiatives that cut across teams, taking responsibility for coordination and execution from initial planning through delivery.

You Will:

• Structure and lead high-impact cross-functional projects.
• Coordinate stakeholders and manage interdependencies across functions.
• Identify and remove blockers that could slow execution.
• Keep initiatives aligned with strategic intent, scope, and expected outcomes.
  
  

Improve Organizational Effectiveness and Alignment

You will identify opportunities to improve how the organization operates, makes decisions, and works across functions, helping reduce friction as PayMongo scales.

You Will:

• Identify gaps in processes, systems, operating models, and ways of working.
• Develop and help implement scalable, data-guided improvements.
• Partner with leaders to strengthen decision frameworks and execution practices.
• Support clear communication of strategy, priorities, and key decisions across the company.
  
  

Support Investor, Board, and Key Stakeholder Engagement

You will act as a strategic extension of the CEO in investor-facing matters, helping ensure that company strategy, performance, and risk are communicated clearly, consistently, and with strong data integrity.

You Will:

• Coordinate investor and board materials, communications, meetings, and follow-through.
• Support capital raise activities and diligence preparation.
• Work closely with Finance, Legal, and business leaders to build fact-based investor narratives.
• Anticipate stakeholder questions and prepare leadership for high-stakes engagements.
• Support engagement with strategic partners and vendors when delegated by the CEO.
  
  

Tools You Will Work With

You Will Use Collaboration, Analytics, Project Management, And Reporting Tools To Structure Decisions, Track Company Priorities, Prepare Executive Materials, And Coordinate Cross-functional Work. These May Include:

• Google Workspace (Docs, Sheets, and Slides) - for analysis, executive briefs, presentations, planning, and communication.
• OKR and project tracking tools - for translating priorities into milestones, ownership, and execution visibility.
• Internal dashboards and analytics tools - for monitoring performance, identifying risks, and supporting data-guided decisions.
• Process mapping, documentation, and communication tools - for improving operating models and coordinating stakeholders.
  
  

You do not need to have worked with every specific platform, but you should be comfortable learning new tools and using data and documentation to drive clarity and execution.

What We’re Looking For

We are looking for a senior, high-ownership operator who combines strategic problem solving, disciplined execution, executive communication, and strong stakeholder judgment.

You Should Bring:

• Advanced ability to structure ambiguous business problems, synthesize complex information, and develop clear recommendations.
• Strong program and project management capability, including experience driving cross-functional initiatives with multiple senior stakeholders.
• Comfort working with qualitative and quantitative data to inform business decisions.
• Advanced executive communication skills, with the ability to communicate clearly, concisely, and confidently with senior leaders.
• Strong stakeholder management and influencing skills, particularly when driving outcomes without formal authority.
• Sound judgment and discretion in sensitive, high-stakes situations.
• Advanced understanding of how product-led, technology-driven organizations operate.
• The adaptability to balance strategic thinking with hands-on execution in a fast-changing environment.
  
  

Nice to Have

Experience or knowledge in the following would be particularly helpful:

• Working knowledge of the fintech, payments, financial infrastructure, or platform ecosystem.
• Experience supporting investor relations, board communications, capital raising, or other high-stakes external stakeholder engagements.
• Exposure to scaling technology businesses where cross-functional alignment and operating discipline are critical.
  
  

You do not need to have experience in every area above. What matters most is your ability to bring structure to ambiguity, influence across senior stakeholders, and consistently turn priorities into execution.

What Success Looks Like

Success in this role means helping the CEO and Executive Team operate with greater clarity, speed, and execution discipline while ensuring that PayMongo’s most important priorities continue to move forward.

You Will Be Successful When You:

• CEO- and Executive-level strategic initiatives are delivered with clear ownership, strong follow-through, and measurable progress.
• Executive decisions are supported by timely, high-quality analysis and recommendations.
• Cross-functional teams remain aligned on priorities, dependencies, and next steps.
• The company’s operating rhythm becomes clearer, more disciplined, and more effective.
• Investor and board engagements are well-prepared, coordinated, fact-based, and supported by reliable data.
• Execution friction is surfaced early and addressed before it slows critical company priorities.
  
  

Team & Reporting

You will report directly to the Chief Executive Officer and sit within the Office of the CEO. You will be responsible for overseeing the work of the Executive Assistant to the CEO.

You will work closely with the Executive Team and leaders across Product, Engineering, Operations, Finance, Commercial, Legal, and People. You will also interact with investors, strategic partners, and vendors when delegated by the CEO.

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