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 customers

• A 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.  

• Lead 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 lifecycles 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. 

• 8+ years of progressive experience leading complex enterprise technology projects and large-scale cross-functional initiatives, preferably within retail, omnichannel commerce, or consumer-facing organizations.

• Bachelor's degree in management information systems, Business Administration, Communications or another technical or business technology field is required.

• Experience with enterprise PPM and financial planning tools strongly preferred.

• Prior experience managing programs exceeding $1M+ budgets preferred

• Proven experience leading enterprise-scale programs with multiple concurrent workstreams, cross-functional stakeholders, and distributed technology teams. 

• Demonstrated ability to influence executive leadership and communicate effectively with both technical and non-technical audiences, including VP and C-level stakeholders. 

• Experience driving strategic business transformation initiatives with measurable operational or customer impact. 

• Experience establishing delivery frameworks, operational processes, KPIs, and reporting standards across large programs. 

• Excellent collaboration and communication skills.

• Strong financial acumen and project management skillset.

• Comfortable working in a hybrid working arrangement – in office 3 days a week.

• Leadership of cross functional teams across IT, product, and business operations.

• Manage vendor relationships, contracts, and service delivery for project workstreams.

• Drive risk, issue, and change management to ensure project success.

• Extremely organized and self-motivated, detail oriented and strong work ethic

• Thrive in a fast-paced, deadline driven environment

• Strong relationship building skills with the ability to work with all levels

• Experience with Microsoft Office, Jira, Confluence, Planisware, AI Tools

If you see yourself in this role, but fall short in any areas above, apply anyway!  We love to invest in our team members!

Tailored Brands is North America’s leading specialty retailer of menswear, famous for world-class customer service and unique offerings like tailoring and custom suits. We are best known by our brands, including Men’s Wearhouse, Jos. A. Bank, K&G Fashion Superstore, and Moores Clothing for Men in Canada. 

We are emerging from the pandemic with incredible momentum. We own a unique and special market segment experiencing record-level demand. This has inspired our 3-year journey to become Legendary; an exciting strategy that leans heavily upon a strong technology foundation.

With over 1,000 stores across the US and Canada, 15,000 employees, and over 35 million customers, we’re the perfect size!  Large enough to demand leading-edge enterprise-worthy technology, but small enough to move quickly and empower our teams with significant scope & autonomy.  

This role is eligible for healthcare including medical, dental and vision, retirement savings (401k with a company match), income protection programs such as life, accident and disability insurance, paid time off for sick leave, vacation, bereavement, jury duty, and holidays, wellbeing program, commuter, adoption assistance, education assistance, legal services, and employee merchandise discounts. For more detailed information go Tailoredbrands.com/working-here/people-culture.

We understand the demands of work, school, family, and personal responsibilities. Through our work-life resources and programs we offer services for every stage of life to help you manage the day-to-day needs. We offer programs such as: 

• Meeting-Free Fridays (encouraged) | so you can catch up on work and self-development

• Summer Fridays | from Memorial Day to Labor Day so you can enjoy a head-start to the weekend 

• Holiday Early Departure | close out early the business day before a company observed holiday  

• Ability to sit and work at a computer keyboard for extended periods of time

• Ability to stoop, kneel, bend at the waist, and reach daily

• Able to lift and move up to 25 pounds occasionally

• Must utilize visual acuity, speech and hearing, hand and eye coordination and manual dexterity necessary to operate a computer and office equipment

• Hours regularly 40 hours per week, as work dictates from our corporate office in Houston, TX, with a requirement to work onsite three (3) days per week. 

Note: To perform this job successfully, an individual must be able to perform each essential duty satisfactorily. The requirements listed are representative of the knowledge, skill, and/or ability required and are not intended to be an exhaustive list of all duties, responsibilities or qualifications associated with this job.