IT Director-Retail Capabilities

Information Technology Dodgeville, Wisconsin


Lands’ End has outlined a strategy to grow sales $2+ billion over the next five years.  This growth will be enabled by evolving to meet the uni-channel expectations of our customers – providing flexibility to engage and shop through various channels including mobile and desktop e-commerce, call centers, stores, and marketplaces.  A key growth element of this vision is to expand the Lands’ End retail footprint by opening 50+ stores over the next five years and provide compelling in-store shopping experiences that bring to life the connections between the digital and physical interactions of our customers.  These experiences include concepts like universal baskets to enable seamless in-store and on-line checkouts, digital fitting rooms, store pickup and shipping for online orders, and analytically driven personalization experiences.


Job Description


The IT Director for Retail Capabilities will have responsibility for leading the technology teams that deliver and support the retail platforms used within Lands’ End’s stores including capabilities like Point of Sale (POS), store kiosks, digital signage, and clientelling applications.  In addition, this leader will be responsible for working with cross functional teams across the enterprise to envision and ultimately deliver a multi-year roadmap that will introduce new capabilities like universal basket checkout experiences, digital fitting rooms, store fulfillment of online orders, personalization, workforce management, and digital training.


As the overarching IT leader for this critical growth area, this role will be responsible for all facets of these solutions including strategy, architecture, development and operations.  In addition, this leader will also be responsible for collaborating with Lands’ End’s retail teams to develop a cost-effective, repeatable and saleable model to enable Lands’ End to open multiple new stores each year.


You will formulate, implement and drive IT strategies that optimize agility, creativity and flexibility. You will leverage your deep understanding of retail capabilities to deliver solutions capable of supporting Lands’ End’s long-term objectives and you will provide detailed, hands-on direction to your team of IT professionals (made up of both internal and external team members).



  • Reports to Chief Information Officer


Sample of Key Responsibilities

  • Directly building, mentoring and leading an IT team focused on delivering world-class retail capabilities including Point of Sale, kiosks, digital signage, clientelling applications, universal basket transactions, personalization, workforce management, etc.
  • Refining and optimizing a new store opening operating model including repeatable playbooks, in-store technology improvements, alternative and competitive sourcing for hardware/software/labor, etc.
  • Maturing the development methodologies used to deliver IT retail capabilities – moving Lands’ End toward more agile, nimble, robust practices.
  • Collaborating with cross functional business teams in retail, e-commerce, operations and finance to identify strategic opportunities that will create seamless, uni-channel experiences for our customers.
  • Collaborating with IT peers to align practices, leverage enterprise technologies, coordinate resource needs and timing, and engage infrastructure & security teams.
  • Defining and delivering application roadmaps and technology platforms for our retail capabilities with features that support Lands’ End’s business strategies.
  • Reviewing on-going capability enhancement requests and working with your teams to sequence the delivery of these appropriately into the system roadmaps.
  • Leading the identification, evaluation, and selection of third-party technologies and consulting partners to deliver solutions that meet strategic retail objectives.
  • Enhancing the operational support model necessary to provide adequate responsiveness required in a retail environment.
  • Collaborating with enterprise architects to leverage standards to drive our application portfolios toward a simpler, more streamlined set of platforms.



  • Proven success in a fast-paced environment. Must have retail experience associated with physical stores, e-commerce and uni-channel business models.
  • Prior experience with large-scale retail store chains and supporting technology platforms.
  • Proven ability to effectively lead projects from inception through to implementation.
  • Strong Return on Investment (ROI) mindset to strategically plan for and execute capabilities that deliver meaningful results.
  • Experience with executive communications and interactions.
  • Excellent listening, verbal, written communication and interpersonal skills.
  • Demonstrated ability to facilitate groups/teams to include planning, presentations and moderation.
  • Demonstrated ability to analyze information, solve problems and adapt to different work environments.
  • Demonstrated effective planning and organizational skills through previous work assignments.
  • Ability to negotiate for resources, budget dollars and contracts for projects.