Product Chief of Staff

Product Chief of Staff
The Role

We're looking for a Product Chief of Staff to partner directly with our Chief Product Officer (CPO) and drive operational excellence across Product, Design, and Engineering. You'll own the operating cadence that keeps our R&D organization aligned and accountable, while leading strategic initiatives that span teams and functions.

This role requires someone who thinks strategically, executes relentlessly, and earns trust through sound judgment and results. You'll turn priorities into action, bring clarity to complex problems, and ensure decisions translate into measurable outcomes. You'll also serve as a candid thought partner to the CPO, identifying challenges, challenging assumptions, and taking ownership of work that enables the CPO to stay focused on building.

This is not a traditional administrative Chief of Staff role. We're looking for a hands-on operator who thrives in a high-velocity environment and can influence across teams without relying on formal authority.
What you'll do

• R&D Operations & Execution
  
  • Own the operating cadence across Product, Design, and Engineering, including quarterly roadmap planning, OKRs, leadership meetings, and decision tracking.
  • Drive accountability and follow-through, ensuring priorities stay on track and decisions turn into action.
  • Build and maintain a weekly product scorecard tracking key metrics, including shipping velocity, call quality, and activation.
• Strategic Initiatives & Cross-Functional Leadership
  
  • Lead 2-3 high-priority initiatives each quarter, taking ambiguous problems from strategy through execution and measurable results.
  • Partner across Product, Engineering, GTM, and Client Success on initiatives such as new market opportunities, pricing and packaging, product launches, and company-wide AI adoption.
  • Keep distributed teams aligned, ensuring clear communication and coordination between US-based leadership and our Engineering organization in Spain.
• CPO Partnership & Executive Communications
  
  • Serve as a trusted thought partner to the CPO, bringing candid perspectives, identifying risks, and helping prioritize competing demands.
  • Anticipate challenges, resolve issues independently, and close loops that would otherwise require the CPO's attention.
  • Own product-related executive and board updates, translating complex information into clear insights, recommendations, and decisions.
• Organizational Effectiveness
  
  • Improve how teams collaborate, communicate, and execute as the organization scales.
  • Support product and design recruiting, organizational planning, and the integration of new teams and processes.
  • Drive clear internal communications around product priorities, decisions, and launches.

Characteristics

Must-haves

• Exceptional judgment and discretion, with the ability to navigate sensitive business and organizational matters.
• Relentlessly execution-oriented. You take ownership, close loops, and deliver results without needing to be chased.
• Highly structured thinker and exceptional writer who can turn complex, ambiguous problems into clear recommendations and actionable plans.
• Proven ability to influence senior leaders and drive accountability across teams without formal authority.
• Strong business and product fluency, including financial metrics, customer data, and product analytics.
• Comfortable operating at high speed, balancing competing priorities, and working across international time zones.
• AI-native in how you work, using AI tools to analyze, automate, and significantly improve productivity.
• Highly collaborative, low-ego, and effective in a remote-first environment.

Nice-to-Haves

• Previous Chief of Staff, Business Operations, Strategy, or Product Operations experience at a high-growth startup.
• Background in management consulting, investment banking, or a similarly analytical environment.
• Experience in SMB SaaS, AI, voice technology, or legal tech.
• Experience with product operations, roadmap planning, or cross-functional product launches.
• Experience working with distributed or European teams.

What Success Looks Like

• You establish a consistent, effective operating cadence across Product, Design, and Engineering, with clear priorities, measurable goals, and strong accountability.
• You drive 2-3 strategic initiatives per quarter from ambiguity to successful execution, delivering meaningful business outcomes.
• You create a reliable, data-driven view of product performance that helps leadership make faster, better decisions.
• You strengthen alignment between R&D, GTM, and Client Success, ensuring teams are informed and launches are coordinated.
• You measurably free up the CPO's time by independently owning operational priorities and resolving issues before they require escalation.
• You build processes and systems that scale, allowing the organization to operate effectively without constant executive intervention.

Life at Smith.ai

This is a full-time, remote position with a base salary that ranges between $215,000-$250,000 per year. In addition to salary, you are eligible for equity and a competitive benefits package that includes medical, dental, vision, life insurance, 401k, and a Flexible Time Off program.