Director of Product

• Set a multi‑year product vision and translate it into clear strategies, multi‑quarter roadmaps, and measurable outcomes. Hold yourself and the team accountable to business KPIs
• Operate with a CEO mindset for your portfolio: know the numbers cold, make focused bets, and pivot quickly based on customer truth and data
• Drive end‑to‑end execution across multiple streams of work. Create clarity from ambiguity, sequence milestones, manage risks, and remove blockers to deliver reliably
• Raise the bar for product craft and reliability. Establish quality standards, review work rigorously, and ensure we ship intuitive, durable solutions that scale
• Lead customer‑backwards discovery. Pair qualitative insights with quantitative analysis to identify the highest‑leverage problems and validate solutions
• Build and lead a small team of Product Managers. Coach for outcomes, provide clear expectations, and develop talent through feedback, modeling, and opportunity
• Influence broadly without relying on authority. Align executives and cross‑functional leaders through clear narratives, crisp decision docs, and transparent tradeoffs
• Partner deeply with Engineering and Design to balance speed, scope, and technical integrity. Make pragmatic decisions that protect long‑term velocity
• Orchestrate go‑to‑market with Sales, Marketing, and Customer Success. Define positioning, enablement, rollout plans, and feedback loops to drive adoption
• Institute operating rhythms that reinforce learning: post‑launch reviews, experiment cadences, KPI health checks, and decision logs
• Manage a portfolio of bets. Allocate resources, sunset low‑ROI work, and double down where impact is greatest
• Model Canary’s operating principles: bias for action, bold choices, customer truth, rally and inspire, learn and adapt. Reinforce these behaviors across the team

• 8+ years in product management with 2+ years managing PMs, ideally in B2B SaaS
• Track record of shipping successful products from 0 to 1 and at scale, with clear business and user impact
• Strong product judgment, customer empathy, and the ability to simplify complex problem spaces
• Comfortable operating in a fast-paced, high-growth environment with evolving priorities
• Excellent written and verbal communication skills and cross-functional leadership

Experience in hospitality tech, messaging/communications, payments, or AI-powered products

• Canary Days: company wide days off each month
• Self Improvement Club: budget for personal goals
• Professional Development Chats: budget for cross functional professional development
• Travel Reimbursement: stipend for visiting offices in New York, San Francisco or Dallas
• Personal Travel Reimbursement: credit for stays at hotels that Canary works with
• Opportunity to earn a discretionary bonus and/or equity