Senior Project Manager

AI overview

Drive the full project lifecycle through strategic planning and execution in a dynamic environment, collaborating with cross-functional teams to ensure project success.

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

Scope and Ownership

  • Own the full end-to-end project lifecycle from initiation through planning, execution, and delivery for technical and operational projects, operational, and product-driven initiatives.
  • Partner with Product, Engineering, and cross-functional stakeholders, including external clients to define scope, deliverables, success criteria, and timelines.
  • Collaborate closely with Product Management on roadmap planning, feature delivery, and release readiness.
  • Maintain a deep understanding of product and technical requirements to ensure accurate scoping and alignment.
  • Drive multiple parallel projects while balancing priorities, dependencies, and trade-offs.
  • Take accountability for outcomes and ensure projects are driven to completion

Execution and Delivery

  • Develop and manage project plans and milestone roadmaps that provide visibility, alignment, and predictable delivery outcomes.
  • Support product delivery workflows including backlog refinement, sprint planning, release planning, and go-to-market readiness.
  • Facilitate cross-functional meetings, working sessions, and status checkpoints with both internal teams and external stakeholders.
  • Monitor schedule, scope, resource allocation, and risk to ensure timely and efficient delivery.
  • Identify risks, blockers, and dependencies early; define mitigation strategies and escalate when needed.
  • Resolve execution issues quickly to maintain delivery velocity.
  • Apply Agile, Scrum, Waterfall, or hybrid methodologies based on project needs.
  • Use project management tools (e.g., Jira, Asana, Smartsheet) to track execution and progress.

Leadership

  • Lead cross-functional teams with influence, clarity, and accountability.
  • Communicate clearly and confidently with stakeholders at all levels, including external customers and executive leadership.
  • Create and deliver executive-level reports, dashboards, and status updates that communicate progress, risk, and impact.
  • Navigate ambiguity and high-pressure situations with structure and confidence.

Operations and Excellence

  • Drive continuous improvement through retrospectives, process refinement, and adoption of best practices
  • Contribute to the development and evolution of PM standards, tools, and delivery processes
  • Improve SDLC efficiency, execution quality, and delivery consistency across teams
  • Strengthen alignment between product planning and delivery execution through improved intake, prioritisation, and capacity planning processes
  • Maintain strong operational discipline through structured planning, reporting, and governance

Benefits

  • Bachelor’s degree in business, engineering, technology, or related field (or equivalent experience)
  • 8+ years of project management experience, preferably in SaaS, software development, or digital product environments.
  •  Experience working closely with Product Management teams on roadmap execution, feature delivery, and release coordination
  • Strong hands-on experience managing Agile teams and delivery, including sprint planning, backlog refinement, release planning, and cross-team dependency management.
  • Demonstrated experience managing projects using Agile, Scrum, Waterfall, or hybrid methodologies in customer-facing environments.
  •  Proven ability to lead cross-functional teams and drive alignment across diverse stakeholder groups.
  • Strong analytical, organizational, and decision-making skills with the ability to balance competing priorities.
  • Exceptional communication and stakeholder management skills, including experience collaborating directly with external customers and presenting to executive leadership.
  • Ability to navigate ambiguity, identify risks early, and drive solutions proactively in high-impact delivery scenarios.
  • Ability to navigate ambiguity, identify risks early, and drive solutions proactively.
  • Proficiency with project management tools (e.g., Jira, Asana, Smartsheet) and project reporting frameworks.
  • 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.

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.We believe a thoughtful blend of technology and hands-on support leads to better restaurant outcomes. Our vision is to provide this combination of software and service to every brand so they can scale their digital business with less effort. Looking ahead, our team is not only focused on solving today's problems but on anticipating and addressing tomorrow's challenges. Through our partnership with restaurants, we aim to help expand their digital footprint and build stronger connections with their customers.

View all jobs
Ace your job interview

Understand the required skills and qualifications, anticipate the questions you may be asked, and study well-prepared answers using our sample responses.

Senior Project Manager Q&A's
Report this job
Apply for this job