Product Chief of Staff

About Smith.ai

Smith.ai runs end-to-end intake for law firms, combining AI efficiency with a network of more than 500 live, North America-based agents. Intake is a sales funnel, and most law firms aren't running it well. Smith.ai exists to fix that. We ensure every call is answered, every lead is qualified, and every opportunity that should convert, does. Built on more than 30 million calls and a decade of experience with over 4,000 small to mid-sized law firm clients, Smith.ai helps firms win more clients.

We're a lean, profitable-minded team going deep on the legal vertical, and everything we build and market is with that lens. This is a high-impact, high-ownership role for someone who thrives on bringing structure to ambiguity, driving execution, and helping a fast-moving organization operate at its best.

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

Here at Smith.ai, we're laser-focused on our mission of helping small and medium businesses succeed. We strive to test, learn, and improve, while continuously developing our solutions, our operations, and our team members. We're a fast-growing and dynamic startup that values collaboration and innovative thinking. We are an equal opportunity employer and believe diversity makes teams better and that discrimination based on race, gender, or anything else is self-defeating.

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.

Product Chief of Staff