Chief of Staff (Product Org)

Smartly•New York, NY

21d•$140,000 - $190,000

About The Position

Smartly.io is currently looking for a Chief of Staff to join our growing team! The Chief of Staff to the Chief Product Officer (CPO) is a senior, highly trusted partner who amplifies the effectiveness of the Product organization and its leader. This role blends strategy, analytics, and execution, acting as an extension of the CPO across planning, decision-making, and cross-functional alignment. This is not an administrative role. It is a thought partner and operator role designed for someone with top-tier strategic rigor, deep analytical skills, and experience driving complex initiatives inside high-growth or Big Tech environments. You will help turn product vision into reality by shaping strategy, driving operating cadence, surfacing insights, and ensuring the Product org delivers measurable customer and business impact.

Requirements

8–12+ years of experience across a combination of:
Top-tier management consulting (e.g. McKinsey, BCG, Bain or equivalent)
Product strategy, business operations, or strategy & operations roles at a high-growth or Big Tech company
Proven experience working closely with senior executives and influencing at the C-level
Experience operating in complex, platform-based SaaS or technology businesses strongly preferred
Advanced proficiency in SQL and strong working knowledge of Python for analysis and modeling
Comfort working directly with large datasets, dashboards, and experimentation results
Ability to move seamlessly between quantitative analysis, qualitative research and strategic synthesis
Exceptional structured thinking and problem-solving ability
High judgment, discretion, and ability to operate in ambiguity
Strong executive presence with the ability to challenge constructively
Bias toward action, clarity, and impact

Responsibilities

Serve as a primary strategic advisor to the CPO on product vision, portfolio tradeoffs, org design, and long-term bets
Lead structured problem solving on ambiguous, high-stakes questions (e.g. build vs. buy, sequencing of AI investments, platform vs. feature tradeoffs)
Prepare clear, data-backed narratives for the CEO, executive team, and Board
Drive the Product organization’s operating cadence: planning cycles, roadmap reviews, KPI reviews, and executive updates
Track and unblock critical cross-team initiatives spanning Product Management, Design, Engineering, Product Marketing, and AI Platform teams
Ensure alignment between product strategy, commercial priorities, and go-to-market execution
Act as a connective layer between Product and key partners including Engineering, Sales, Marketing, Customer Success, and Finance
Lead or support high-impact, cross-functional programs (e.g. major platform launches, AI initiatives, org transformations)
Identify and proactively resolve misalignment before it becomes execution risk
Craft concise, compelling written and visual materials for exec forums, Board meetings, and customer-facing moments
Pressure-test messaging to ensure product strategy is clear, credible, and grounded in customer value
Raise the bar on clarity, precision, and decision quality across Product leadership communications
Own deep-dive analysis to inform new initiatives or key decisions (prioritization, investments, and KPI tracking)
Draw customer and business insights from product usage, adoption, retention, monetization, and roadmap performance
Build and maintain core dashboards
Travel with CPO when needed to provide on-the-ground support for important events and team activities