Sr Project Manager - Customer Experience & AI Enablement

Waterfield Tech

1d•Remote

About The Position

Waterfield Tech enables companies to select, design, and deploy tailored customer engagement solutions from the world’s leading providers enhanced by cutting edge Applied AI. The results are happier customers, enhanced insights, and lower costs. Once live, we empower companies to support, optimize, and modernize those solutions and AI applications, leading to lower risk and increased efficiency. Our client-centric process and track record of success have earned the trust of clients around the world when it comes to customer interaction. We value our people—their diversity, their dedication, and their commitment to customer satisfaction. We encourage each other. We understand the value of hard work and the importance of a healthy balance. We’re all on the same page… even though we may get there from different perspectives. All in all, it’s a pretty cool place to be and we’re growing our global team of engineers, sales professionals, and creative souls. 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.

Requirements

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.
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.
PMP certification required (or equivalent recognized certification such as PRINCE2 Practitioner or PgMP).
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.
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.
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.

Nice To Haves

Master's Degree a plus.
Agile / Scrum certifications a plus (CSM, PMI-ACP, SAFe).
ITIL certification recommended.
Change management certification a plus (e.g., Prosci ADKAR).
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.
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.

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.