Senior Project Manager - Customer Experience & AI Enablement

Position Summary

Waterfield Tech is seeking an experienced Senior Project Manager to lead the delivery of complex customer experience and contact center modernization programs across a portfolio of cloud platforms, multi-vendor integrations, and AI-driven capabilities. This individual is the senior delivery owner for assigned engagements - guiding customers through the transition from legacy environments to modern, AI-enabled customer engagement solutions while managing scope, schedule, financials, and risk through the full project lifecycle.

The Senior Project Manager has the authority to run the project on a day-to-day basis, partners closely with technical and customer stakeholders, and serves as the central point of accountability for delivering best-in-class customer service. This role is a critical leader on multi-vendor, integration-heavy engagements, including AI enablement projects that bring conversational AI, agent assist, and analytics into production alongside core contact center and unified communications platforms.

Key Responsibilities

• Manage a portfolio of complex, multi-workstream projects spanning customer experience, contact center, unified communications, Applied AI, and cloud migration engagements; own the full project lifecycle including scope, schedule, resource planning, budget, risk, change, and stakeholder communication.
• Review proposal material, SOWs, and executed contracts to determine scope; request resources from matrixed support organizations; ensure contractual compliance with all RFP and SOW terms while delivering best-in-class customer service.
• Partner with sales, solution consulting, and pre-sales engineering on opportunity scoping, level-of-effort estimation, and Statement of Work development for new and in-flight customer expansions.
• Lead go-live event planning, production change management, and Day 1 post-launch incident support; lead transition to Day 2 support per Waterfield Tech standards.
• Build and motivate cross-functional project teams; serve as the central point of contact between technical teams, customer stakeholders, vendors and subcontractors, and Waterfield Tech leadership.
• Establish and maintain client relationships, manage expectations of project sponsors, and manage external vendor relationships including SOWs, deliverable acceptance, and invoice validation.
• Identify, assess, and mitigate risks and issues; manage project change requests through formal change control with impact analysis, approvals, and downstream communication.
• Lead AI enablement projects end to end - from discovery and use-case definition through production cutover and post-go-live tuning - including conversational AI, virtual agents, agent assist, real-time analytics, and AI-powered self-service.
• Apply AI-powered solutions to project delivery itself, including automated status reporting, predictive risk analysis, intelligent meeting summarization, action-item tracking, and automated documentation generation.
• Adhere to stage-gate quality and control guidelines and Waterfield Tech project management standards, including booking, time entry, and project operations within Microsoft Dynamics 365 / Project Operations.
• Provide status reporting on milestones, deliverables, dependencies, risks, and issues to leadership and stakeholders; deliver progress reports, dashboards, and steering committee updates.
• Track and report customer-outcome metrics at the project level - including CSAT, NPS, on-time delivery, schedule variance, and cost variance - and surface trends and corrective actions to PMO leadership.
• Conduct lessons-learned sessions upon project closure, produce after-action reports, and contribute to PMO process improvement and continuous improvement initiatives.
• Provide coaching, mentorship, and on-the-job training to junior project managers, project coordinators, and team members.
• Continue professional development to keep abreast of emerging technologies, methods, and best practices; perform other duties as assigned by leadership.

Primary Technical Project Experience (One or more of the following required)

• AI enablement projects, including conversational AI, virtual agents, agent assist, real-time analytics, and AI-powered self-service.
• Five9 contact center implementations and migrations (inbound, outbound, blended, WEM).
• Genesys Cloud CX implementations and migrations from legacy Genesys Engage / PureConnect or other ACD platforms.
• Cisco Webex Contact Center implementations and migrations, including Webex Calling deployments and Webex Connect / digital channel rollouts.
• Avaya Cloud Office (ACO) implementations and migrations from Avaya Aura / IP Office to ACO.
• Avaya Aura Communication Manager (CM) v8 implementations and upgrades through CM v10.2, including experience with Avaya peripheral products and contact center applications such as Proactive Outreach Manager (POM), Customer Browser Adapter (CBA), post-call survey, and Avaya Experience Portal (AEP).
• Zoom Contact Center and Zoom Phone deployments, including integrations with Zoom Workplace.
• Multi-vendor / multi-platform delivery, including projects that combine two or more of the above with CRM, WFM, QA, and analytics integrations.
• Legacy-to-cloud migration delivery, including dual-running cutover plans, number porting, contact-flow translation, and reporting reconciliation.

Education, Experience & Qualifications

Education & Experience

• Bachelor's Degree from an accredited college or university required; Master's Degree a plus. Emphasis in Project Management, Information Technology, or Business Leadership preferred. Equivalent work experience will be considered.
• Required: Prior experience as a Technical Project Manager at a manufacturer or vendor business partner (e.g., Avaya, Cisco, Genesys, Five9, Zoom, Microsoft, an AWS Partner Network member, or similar) delivering customer-facing projects on behalf of the partner. Internal/end-customer-only PM experience is not equivalent for this role.
• 8+ years of experience managing complex technical projects, including tracking and planning.
• 4-7 years of related experience in a project management or delivery leadership role.
• 5+ years of experience working with business stakeholders within a cross-functional matrix environment.
• 1+ years of experience gathering and documenting requirements directly with the client or business.
• Extensive understanding of project and program management principles, methods, and techniques (Waterfall, Agile, Hybrid).
• Demonstrated experience leading multi-vendor delivery and integration projects across customer engagement, telephony, and cloud platforms.
• Demonstrated experience leading legacy-to-cloud migrations and platform transitions for enterprise customers.

Technical Project Experience (preferred but not required)

• Telecom: VoIP, IVR, Contact Center, Automated Dialers, CCaaS platforms.
• Telephony platforms: Avaya (Red/Aura), Cisco, Genesys, Five9, Zoom, Verint, Calabrio.
• Cloud: AWS.
• Network: SD-WAN, MPLS, firewalls, VPNs.
• Data center migrations, application launches, and cloud transitions.
• AI and automation platform deployments.

Certifications

• PMP certification required (or equivalent recognized certification such as PRINCE2 Practitioner or PgMP).
• Agile / Scrum certifications a plus (CSM, PMI-ACP, SAFe).
• ITIL certification recommended.
• Change management certification a plus (e.g., Prosci ADKAR).

Technical Proficiency

• Intermediate to advanced proficiency with MS Project (or Smartsheet), Word, Excel, Visio, PowerPoint, and SharePoint.
• Experience with Microsoft Dynamics 365 / Project Operations for booking, time entry, and project operations.
• Experience with AI-powered project management tools and platforms (e.g., Microsoft Copilot, ChatGPT, Claude, AI-enhanced PPM tools).
• Familiarity with modern project portfolio management and collaboration platforms.

Soft Skills

• Self-motivated leader with strong diplomatic and motivational skills, including the ability to lead up, across, and down multiple business and technology organizations.
• Excellent attention to detail with a proven ability to adapt to shifting priorities, competing demands, and timelines through analytical and problem-solving capabilities.
• Ability to execute many complex tasks and projects simultaneously, working effectively as a team member and independently.
• Proven ability to work creatively and analytically in a problem-solving environment, demonstrating teamwork, innovation, and excellence.
• Outstanding oral and written communication skills across all organizational levels, including executive audiences.
• Demonstrated ability to align diverse stakeholders and resolve cross-functional tensions constructively.
• Adaptable and innovative; thrives in environments of rapid change and ambiguity.

Physical Requirements

• Ability to sit for extended periods (up to 80% of the time)
• Ability to lift or carry objects up to 10 lbs.
• Frequent use of computer, telephone and standard office equipment.
• Ability to travel occasionally for client meetings, training or installations.

Position Information

Position Status: Full time

Location: Remote

Benefits: Comprehensive package including medical dental, vision, LTD, life, AD&D, 401(k), Paid time off, sick time, holidays and more.