Associate Director Project Management Job at Checkmate, Remote

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  • Checkmate
  • Remote

Job Description

The Associate Director of Project Management plays a strategic and operational leadership role in guiding critical, cross-functional initiatives. Reporting to the Director or VP of Project Management, this individual will lead a team of project managers, ensure the delivery of enterprise-level programs, and optimize project execution across technical and business teams.

This is a high-impact position requiring exceptional leadership, stakeholder management, and process design in a fast-paced, evolving environment.

Essential Job Functions:

  • Lead and mentor a team of project and program managers responsible for initiatives across technology, partnerships, and customer operations
  • Oversee the planning, tracking, and execution of complex projects related to product deployment, integrations, platform enhancements, and partner onboarding
  • Collaborate closely with engineering, product, partnerships, and support teams to align project execution with business goals
  • Build and optimize project governance frameworks, tools, and performance metrics
  • Act as a thought partner to senior leadership on project prioritization, risk mitigation, and capacity planning
  • Ensure consistent reporting and visibility into project status, blockers, and resource allocation
  • Help standardize and scale project management methodologies across teams (Agile, hybrid, or waterfall as needed)

100 % Remote

$135,000 to $150,000

Requirements

  • 7–10 years of experience in project/program management roles, ideally with 2+ years managing project teams
  • Strong background in SaaS, restaurant tech, or a comparable fast-moving industry
  • Experience managing large, cross-functional projects or programs with technical and operational complexity
  • Familiarity with common PM tools (e.g., Jira, Asana, Monday.com, Smartsheet)
  • Excellent written and verbal communication skills for executive and technical audiences
  • PMP, CSM, or equivalent certification preferred


Preferred Qualifications

  • Experience in restaurant, food tech, or hospitality systems (e.g., POS platforms, delivery APIs)
  • Exposure to working with enterprise restaurant groups or large-scale implementation projects
  • Proven ability to improve team performance, delivery speed, and cross-functional coordination

Benefits

  • Health Care Plan (Medical, Dental & Vision)
  • Retirement Plan (401k)
  • Life Insurance (Basic, Voluntary & AD&D)
  • Flexible Paid Time Off
  • Family Leave (Maternity, Paternity)
  • Short Term & Long Term Disability
  • Training & Development
  • Work From Home
  • Stock Option Plan

Job Tags

Remote job, Full time, Temporary work, Work from home, Flexible hours,

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