Project Manager

Comply365; Orlando (FL); Hybrid; USD 110,000 - 150,000; Full time

Benefits offered by this job

Unlimited PTO

Flexible work environment

Paid Holidays

401(k) plan with company

Comprehensive benefits package

Job summary

Comply365 is seeking a Senior Project Manager to lead planning, governance, and delivery of enterprise software programs in a hybrid Orlando setting. You will guide cross-functional teams through phases, manage risks, and ensure successful delivery aligned with business objectives.

You will partner with Business Consultants, Product/Engineering, and customers to drive value, adoption, and effective handover. The role emphasizes structured governance and strong stakeholder engagement.

Qualifications

• Proven experience managing complex, multi-phase enterprise software implementations.
• Ability to operate within structured delivery governance frameworks.
• Strong communication and leadership across technical and business teams.

Responsibilities

• Lead and facilitate lifecycle governance and phase gate reviews.
• Develop and execute Project Management Plans to deliver products on time and budget.
• Manage cross-functional delivery teams and stakeholder expectations.
• Provide clear status updates, risks, and decision requirements to executives.

Skills

Cross-functional leadership

Stakeholder communication

Negotiation

Project management

Analytical thinking

Time management

Change management

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.

You will lead a cross functional team of professionals in supporting you to ensure that project expectations are agreed and met. You will work closely with the Business Consultant team to ensure a smooth process from commercial engagement through to project delivery and beyond. You will also work closely with the product management group to provide structured customer feedback based on customer interaction. During the life cycle of the project, you will be the most visible member of the Comply365 team to your customer and the key point of contact throughout the organisation.

This role is hybrid to our Orlando office with the expectation of attending the office 3 days per week.

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 escalation 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 escalation 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.