Senior Project Manager

3 hours ago

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ItsaCheckmate

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SaaS • Hospitality

ItsaCheckmate is a technology company that provides powerful ordering solutions for busy restaurants. Their platform enables restaurants to drive sales and connect with customers through various ordering channels, including web, app, kiosk, and third-party integrations. With its scalable enterprise technology, ItsaCheckmate helps restaurants manage and streamline operations, reduce order errors, and increase productivity. They offer features such as loyalty programs, catering management, QR-code ordering, and unified channel management. Trusted by over 2,400 brands, ItsaCheckmate is dedicated to supporting restaurant growth with innovative digital solutions and a marketplace of integrations.

201 - 500 employees

☁️ SaaS

📋 Description

• ● Drive multiple parallel projects with clarity and structure • ● Maintain a deep understanding of product and technical requirements • ● Resolve blockers quickly and escalate when needed • ● Partner closely with Product, Engineering, and Operations • ● Share crisp, actionable updates with leadership and the C-suite. • ● Continuously improve processes and execution quality. • During the interview process, you will be expected to walk us through real-life examples of complex, large-scale projects you’ve managed and how you navigated challenges, ambiguity, and stakeholder expectations.

🎯 Requirements

• ● Lead the full end-to-end project lifecycle — from initiation through planning, execution, and delivery — for technical and operational initiatives. • ● Drive project execution with a strong bias for action, ensuring forward momentum at all times. • ● Partner with product, engineering, design, operations, and business teams to define scope, milestones, and delivery expectations. • ● Build detailed project plans that offer visibility, transparency, and predictability across stakeholders. • ● Facilitate working sessions, cross-functional syncs, reviews, and checkpoints, keeping alignment tight and communication strong. • ● Identify risks, dependencies, and blockers early; drive mitigation strategies with urgency. • ● Provide clear, structured reporting, dashboards, and project updates — including direct presentations to the C-Suite. • ● Ensure resources are well-utilised, teams are unblocked, and timelines are adhered to. • ● Conduct retrospectives, refine processes, and introduce best practices that improve execution quality and SDLC efficiency. • ● Contribute to the development and evolution of internal PM frameworks, tools, and standards.

🏖️ Benefits

• ● Bachelor’s degree in business, engineering, technology, or a related field (or equivalent experience). • ● 8+ years of project management experience, preferably in SaaS, software development, or digital product companies. • ● Proven success managing technical, cross-functional, fast-moving programs using Agile, Scrum, Waterfall, or hybrid models. • ● Ability to work with ambiguity, ask the right questions, and bring clarity to complex situations. • ● Strong analytical, planning, and decision-making abilities with the skill to balance priorities under pressure. • ● Exceptional written and verbal communication; ability to influence, align, and drive outcomes across stakeholders, including senior leadership. • ● Experience in building and presenting concise project reports and executive summaries. • ● Proficiency with PM tools such as Jira, Asana, Trello, Smartsheet, or similar. • ● Professional certifications (PMP, CSM, etc.) are a plus. • ● Must be flexible to work during US hours (until at least 5 PM EST), and must have their own system/work setup for remote work.