Head of Operations, Arcade Software

• We’re looking for someone who wants to help shape the future of the company — not just manage existing systems. This role is ideal for someone who wants to operate at the center of strategy, execution, and company-building alongside the leadership team
• 5–10+ years of experience in operations, strategy, finance, consulting, investing, startup leadership, or similar roles
• Exceptional communication and synthesis skills
• Strong strategic judgment paired with high execution velocity
• Ability to navigate ambiguity and changing priorities calmly
• Strong financial modeling and analytical capabilities
• Proven ability to drive cross-functional projects and influence leaders
• High ownership mentality and bias toward action
• Comfortable operating as both strategist and operator

Desirable

• We’re looking for a highly strategic and execution-oriented Head of Operations to work directly with the CEO and leadership team during a pivotal phase of company growth and evolution
• This is not a traditional “keep the trains running” operations role. We’re looking for someone who thrives in ambiguity, can create clarity from chaos, and can help scale decision-making, prioritization, and execution across the company
• You will act as a strategic partner to the CEO, own company operating rhythms, drive cross-functional initiatives, and help the leadership team operate at a higher level
• Strategic Operations:
• Partner closely with the CEO on company strategy, prioritization, and execution
• Build and maintain financial and operational models to support decision-making
• Translate high-level company goals into actionable operating plans
• Drive strategic planning, quarterly goals, and resource allocation
• Identify operational bottlenecks and propose solutions proactively
• Company Execution & Leadership:
• Run company operating cadence, including leadership meetings, planning processes, and weekly business reviews
• Ensure cross-functional alignment across product, engineering, GTM, marketing, and customer teams
• Improve organizational clarity, accountability, and execution velocity
• Help leadership teams prioritize effectively during periods of rapid change
• Serve as a force multiplier for the CEO and executive team
• Financial & Business Operations:
• Own forecasting, scenario planning, budgeting, and runway analysis
• Support board meeting preparation and investor communications
• Develop KPI frameworks and reporting across the business
• Analyze business performance and recommend operational or strategic changes
• Organizational Scaling:
• Help design scalable processes without introducing unnecessary bureaucracy
• Support recruiting, headcount planning, and organizational development
• Partner with managers to improve team effectiveness and communication
• Step into ambiguous or high-priority initiatives as needed
• What Success Looks Like:
• The company operates with greater clarity, focus, and accountability
• Leadership teams move faster with less friction
• The CEO is spending more time on the highest-leverage strategic work
• Cross-functional initiatives execute reliably
• Operational complexity decreases as the company scales
• Strategic decisions are supported by strong analysis and operational insight