Sr Project Manager - IT

At Tailored Brands, we help people love the way they look and feel for their most important moments. Our Technology team loves the way they feel and thrive at work, with:

Flexible work opportunities, including remote and hybrid options

Small, empowered teams that have fun delivering real value for our customersA culture that values a 50-year legacy while eagerly embracing the future

Want to be part of this? We currently have an exciting opportunity for a Sr IT Project Manager to join our Tailored Technology team. This individual will play a strategic leadership role in driving enterprise technology initiatives that enable business transformation across Tailored Brands. The ideal candidate brings deep experience leading large-scale, cross-functional programs, influencing executive stakeholders, and driving operational excellence across complex technology portfolios.

This role requires balancing strategic planning with flawless execution while navigating organizational change, competing priorities, and enterprise-scale delivery. You will oversee multiple concurrent initiatives, manage dependencies across teams and vendors, and ensure alignment between technology investments and business outcomes.

What you’ll doLead with Impact:
Drive collaboration between business leaders and technology teams to align priorities and execute strategic technology projects. Be the go-to person for navigating complex project phases, transforming agile work into actionable waterfall deliverables that meet business goals. Lead the planning, governance, execution, and successful delivery of complex enterprise technology programs and large-scale business transformation initiatives across retail, digital and corporate platforms.

Portfolio and Executive Leadership:
Establish and lead program governance frameworks, steering committees, executive reporting cadences, and cross-functional decision-making processes to ensure alignment, transparency, and successful delivery across strategic initiatives.

Organizational Influence:
Influence strategic decision making, partner with senior technology and business leaders to prioritize initiatives, evaluate tradeoffs, resolve organizational roadblocks, and align delivery strategies with enterprise objectives.

Orchestrate Seamless Releases:
Take charge of software releases, crafting workflows and schedules to ensure everything runs smoothly. From QA to production, you’ll orchestrate deployments that deliver with precision and minimal downtime.

Monitor Success and Share Wins:
Deliver insightful updates to technical teams and executive stakeholders, highlighting achievements and course corrections where needed.

Validate and Align:
Ensure that project artifacts are created, and the work aligns with audit and security requirements. Monitor work items and ensure the right people do the right tasks, driving the team toward successful project completion.

Communicate with Influence:
Bridge the gap between technical project tracking and business-level reporting, presenting meaningful insights and ensuring stakeholders stay informed at every stage.

Own the Metrics:
Own program financials including multi-million-dollar budget planning, forecasting, resource capacity management, vendor spend oversight, and ongoing cost optimization. Track project health, ensuring you always have a pulse on key metrics. Celebrate the wins and swiftly tackle challenges to deliver with confidence.

Change Leadership:
Lead through change, drive organizational readiness, change management, and adoption strategies for enterprise technology initiatives, ensuring successful implementation and measurable business impact.

Results Oriented:
Manage end-to-end project life cycles with a focus on financial accountability, including budget planning, tracking actuals versus forecast, cost optimization, and rigorous schedule management to prevent scope creep.

Dependency and Risk Leadership:
Manage complex dependencies, coordinate interdependencies across multiple technology teams, vendors, and business units while proactively mitigating enterprise risks, escalations, and delivery challenges.

What you’ll bring8+ years of progressive…