We are looking to hire a highly dynamic Senior Project Manager to join our team. One of the most important traits we are looking for is a bias toward action — someone with the mindset of “let’s get stuff done.” A great project management function acts as the lubricant in the larger machinery of a company — unblocking issues, creating flow, ensuring clarity, and enabling teams to execute at their best. We want someone proactive, structured, and an exceptional communicator (both written and verbal). Someone who has worked in high-pressure environments, stays on top of the details, and brings a strong sense of ownership. A top-tier project manager dives deep into the product, understands its nuances, asks hard questions, and adds real value beyond status reporting. They keep projects on track — and when they don’t, they know exactly why, and drive the path back to course correction.
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) for this role.
What You’re Like
● Action-oriented: You move fast, eliminate ambiguity, and keep momentum strong.
● Detail-driven: You stay on top of every dependency, timeline, and deliverable.
● Proactive: You identify risks before they happen and drive solutions early.
● Clear communicator: You convey information crisply — written and verbal — and keep everyone aligned.
● Calm under pressure: High-stakes situations don’t faze you; you operate with clarity and structure.
● Accountable: You own the outcome — whether things go right or wrong — and you drive the path forward.
● Collaborative: You work across teams with empathy, influence, and purpose.
● Strategic thinker: You understand the product deeply and add value beyond project timelines. Your Daily Work
● 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.
Top Skills
What We Do
Checkmate empowers enterprise restaurant brands with powerful ordering solutions and hands-on support. Our scalable technology enables restaurants to drive sales across channels, including custom websites, apps, kiosks, catering, third-party marketplaces, voice AI, and more. With seamless integrations, smarter analytics, and 24/7 service, Checkmate helps brands conquer their digital goals. Restaurants can launch unique ordering experiences, centrally manage menus, recapture revenue, leverage customer data, and continually adapt with new integrations. Regardless of how you want to grow, Checkmate has the tools and guidance to power, manage, and evolve your digital business.
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