Senior Project Manager

Comply365; Orlando (FL); On-site; USD 90,000 - 130,000; Full time

Benefits offered by this job

Unlimited PTO

Flexible work environment

Paid Holidays

401(k) plan with company

Comprehensive benefits package (health

care, dental, vision, life insurance,

disability insurance, HSA, and FSA)

Paid parental leave (12 weeks primary,

6 weeks secondary caregiver) match

Learning and development opportunities

Employee referral bonus

Job summary

Comply365 in Orlando, FL is seeking a Senior Project Manager to lead the planning and execution of the Project Management Plan, risk and issue management, and stakeholder communications across delivery teams. You will guide phase-gate reviews, manage milestones, dependencies, and change governance, and ensure on-time, on-budget delivery of Comply365 products and services.

Strong leadership and communication with executives are essential.

Qualifications

• Proven experience managing complex, multi-phase enterprise software implementations.
• Ability to operate within structured delivery governance frameworks (stage gates).
• Certification in PMP or PRINCE2 / APMP is preferred.

Responsibilities

• Lead and facilitate Phase Gate Reviews as formal decision forums.
• Develop and execute Project Management Plans to deliver products on time and budget.
• Manage day-to-day delivery, including scope tracking, sequencing, and milestones.
• Track deliverables with tooling and provide accurate reporting.
• Maintain alignment with the PSDD baseline and manage scope changes.
• Handle risk, issues, and escalation with structured governance.
• Coordinate cross-functional teams and stakeholder communications.
• Ensure adoption, handover, and value realization post-launch.

Skills

Gate management

Stakeholder communication

Cross-functional leadership

Project planning & execution

Risk & issue management

Change management

Negotiation

Delivery governance

Education

PMP or PRINCE2 / APMP certification

Tools

Monday.com

Job description

About The Role

As a Senior Project Manager you will be responsible for the planning and execution of the Project Management Plan, encompassing the Project Plan, Risk and Issue Management, Change Management, Stakeholder communications and deliverable/objective tracking.

What You'll Be Doing

• Lifecycle governance & gate management
  • Lead and facilitate Phase Gate Reviews as formal decision forums across the delivery lifecycle, ensuring progression decisions are explicit and criteria-based
  • Validate readiness across scope, dependencies/resources, and outcomes (including completion and quality of prior-phase deliverables), using evidence to confirm the work is ready to progress
  • Ensure phase progression is based on validated readiness and defined criteria; enforce gate classification (hard, conditional, transitional), and challenge, block, or escape when criteria are not met (vs. facilitating progression)
• Project planning & execution
  • Develop and execute Project Management Plans and Project Plans to deliver Comply365 products and services on time and on budget
  • Manage day-to-day operational aspects of delivery, including scope tracking, sequencing, and milestone/objective management
  • Track project deliverables using appropriate tooling (e.g., Monday.com) to enable efficient and accurate reporting
• PSDD baseline integrity & change governance
  • Maintain alignment between delivery execution and the PSDD baseline (contractual scope, sequencing, and commitments)
  • Identify and elevate deviations from the PSDD baseline (scope drift/expansion, dependency changes, resource/sequencing impacts); assess change magnitude and trigger formal governance (and, where needed, regression to the appropriate gate) rather than managing material changes informally
  • Ensure changes are documented, communicated, and governed appropriately
• Risk, issues, and escalation management
  • Perform project risk and issue assessment, mitigation planning, and transparent reporting across delivery, capacity, and financial/revenue exposure
  • Handle escalations, time-critical issues, shifting priorities, and conflicts with a structured approach
  • When exceptions are required, ensure overrides are deliberate and visible decisions supported by formal documentation (risk classification/exposure, mitigation plan, portfolio and/or financial impact assessment) and appropriate executive approvals
• Cross-functional delivery leadership
  • Lead and coordinate matrixed, cross-functional teams (Business Consultants, Product/Engineering, and customer stakeholders)
  • Manage resources engaged in project activities; ensure dependency alignment and sequencing clarity across workstreams
• Stakeholder communication & value articulation
  • Manage stakeholder expectations by providing clear, consistent status, risks, issues, readiness, and decision requirements
  • Articulate the value proposition of products and services to end users, business owners, procurement, and IT
• Adoption, handover, and value realization
  • Ensure readiness for training, launch, and adoption; define adoption metrics prior to go-live and align them to value realization objectives
  • Coordinate structured handover to Customer Support, including documentation/context transfer and known risks/stabilization requirements, to support sustained customer operations
  • Support launch stabilization and monitor early issue patterns to build customer confidence and promote longer-term customer stability
• Continuous improvement
  • Facilitate project evaluations, retrospectives, and structured root-cause analysis; track learning actions to completion

What We're Looking For

• Proven experience managing complex, multi-phase enterprise software implementations (including complex, multi-dimensional software delivery projects)
• Demonstrates ability to operate within structured delivery governance frameworks (stage gates, lifecycle controls, or similar)
• PMP or equivalent PRINCE2 / APMP Project Management Qualification
• Strong understanding of:
  • Dependency mapping and sequencing
  • Scope and change management in a contractual context
  • Risk classification and mitigation strategies
  • Project management techniques and tools (theoretical and practical)
• Experience leading cross-functional, matrixed teams across technical and business domains
• Ability to manage multiple projects simultaneously using strong organizational and time management skills
• Strong negotiation and conflict-resolution skills
• Ability to challenge progression constructively and enforce delivery discipline
• Excellent communication skills, with the ability to:
  • Engage executive stakeholders
  • Translate complex delivery topics into clear, actionable insights
  • Present complex information clearly to executive, technical, and non-technical audiences
• Strong analytical and decision-making capabilities; able to think strategically and tactically by analyzing and prioritizing information
• Ability to develop and maintain strong rapport with clients and cross-functional team members

A few nice to haves

• Experience in SaaS delivery environments, particularly in:
  • Safety
  • Risk management
  • Aviation, aerospace, or defense sectors
• Experience working within regulated or high-compliance environments
• Experience in SaaS delivery environments, particularly in:
  • Safety
  • Risk management
  • Aviation, aerospace, or defense sectors
• Experience working within regulated or high-compliance environments

Why come aboard?

• Unlimited PTO
• Flexible work environment
• Paid Holidays
• 401(k) plan with company
• Comprehensive benefits package (medical, dental, vision, life insurance, disability insurance, HSA, and FSA)
• Paid parental leave (12 weeks primary caregiver, 6 weeks secondary caregiver) match
• Ample learning and development opportunities
• Employee referral bonus

Comply365 is a global company, and our success draws upon our employees' diverse viewpoints, skills, and experiences. We are proud to be an equal opportunity employer, and all qualified applicants will receive consideration for employment regardless of age, race, color, religion, sex, sexual orientation, gender identity, national origin, disability status, protected veteran status, or any other characteristic protected by law.