SQUIRE

Product Manager

• Define and drive the multi-quarter vision for client booking
• Own discovery, booking flows, checkout, confirmations, cancellations, and rebooking
• Ensure experiences scale across geographies, shop types, and future verticals
• Make clear tradeoffs across UX quality, performance, and business goals
• Deeply understand client behavior and friction across the booking funnel
• Improve conversion, rebooking, and retention through data and experimentation
• Elevate trust, clarity, and reliability across critical booking moments
• Partner closely with Engineering and Design to ship performant, high-quality consumer experiences
• Translate strategy into clear requirements and measurable outcomes
• Collaborate with Lifecycle, Marketing, and Data to ensure launches drive impact
• Own key metrics including conversion, rebooking rate, funnel drop-off, and client retention
• Establish clear learning goals and remain accountable to outcomes
• Thoughtfully leverage AI and automation to improve discovery and confidence in booking

Staff Product Manager, Client Booking Experience – B2C

Software Engineer

• Develop, articulate, and drive the execution of a comprehensive technical roadmap that supports SQUIRE’s strategic goals, incorporating feedback from cross-functional stakeholders to ensure engineering efforts remain laser-focused on delivering customer value and driving market differentiation.
• Provide regular status updates and strategic recommendations to the executive leadership team, anticipating challenges and identifying opportunities for innovation or competitive advantage.
• Lead and manage a diverse engineering team, including offshore and nearshore teams of developers working with React, React Native, Node.js and other modern technologies.
• Lead the engineering team in delivering scalable, reliable, and secure software solutions that meet current and future business needs.
• Direct initiatives for the modernization of legacy systems and accelerate the delivery of new product capabilities, prioritizing the strategic integration of AI/ML tools to drive efficiency.
• Champion the application of Generative AI across the entire development lifecycle—from code generation and testing to operational excellence—to maximize engineering velocity and quality.
• Establish and enforce best practices in software development, architecture, and operational excellence.
• Implement generative AI to accelerate the development of code.
• Ensure that the technical and payments architecture supports scalability, performance, and reliability as SQUIRE grows.
• Work closely with the Director, Product Management and Director, Product Design to ensure seamless integration of technical capabilities with product vision and user experience.
• Cultivate an environment of experimentation and learning around emerging AI technologies to maintain a competitive advantage in our technical practices.
• Collaborate with Product Leaders to define clear acceptance criteria, delivery timelines, and post-launch success metrics.
• Collaborate with leaders across Sales, Marketing, and Customer Success to understand evolving customer requirements and market shifts; offer technical insights that help refine go-to-market strategies, product positioning, and customer onboarding.
• Establish a high-performance, AI-driven engineering culture rooted in curiosity, continuous improvement, and open communication, driving the adoption of new AI-powered tools and methodologies.
• Mentor and guide engineering managers and technical leaders, enhancing team productivity, engagement, and performance.
• Develop formal career pathways, rotation programs, and succession plans to nurture future leaders.

VP, Engineering

Product Marketing

• Stand up the Product Marketing function from the ground up
• Own SQUIRE’s product narrative and category positioning
• Lead all major product launches
• Communicate our growing AI capabilities to the Barber community
• Build sales enablement, pricing & packaging strategy, and competitive intelligence
• Serve as a strategic partner to Product, Sales, and Executive Leadership

Director, Product Marketing

Customer Support

• Handle inbound cancellation and downgrade requests, identifying root causes and executing save strategies aligned with policy and commercial guardrails.
• Engage escalated customers who are at risk of churn due to product confusion, perceived value gaps, or operational friction.
• Support inbound upgrade requests, ensuring customers understand plan value and feature differences
• Conduct follow-up outreach after upgrades to drive early adoption and reduce post-purchase churn.
• As a SQUIRE platform expert, provide practical, outcome-oriented guidance: not just how features work, but how customers know features are working for them.
• Act as a trusted product translator during retention, upgrade, and adoption conversations.
• Deliver video-based training sessions ad hoc as needed to achieve product adoption (new shop employees, customers upgrading plans or adding features, etc)
• Reinforce self-service resources and best practices to reduce future friction and support dependency.
• Partner with Support, Customer Success, Product, and Ops to refine save motions, upgrade experiences, and adoption workflows.
• Contribute feedback on where automation can replace or augment manual outreach as volume and maturity increase.

Staff Product Manager, Client Booking Experience – B2C

VP, Engineering

Director, Product Marketing

Customer Experience Specialist