Director of Technology

Purpose of the Role

Own the North American technology estate end to end modernise it and run it with the team on the

ground.

You own all technology in North America: the applications behind retail wholesale e-commerce and the

Kentucky distribution center the infrastructure beneath them the Los Angeles team and contractors and the

vendor relationships. You work closely with the global domain owners such as the Director of Infrastructure

who set direction for their domains worldwide; you make it land in North America. Your mandate is to move a

legacy ERP core and point-to-point integrations to a cloud-based API-driven platform aligned with the global

architecture without disrupting trading. This is not an oversight role: you will be in the architecture the

incident bridge and the code when it matters and you are the senior technology leader the business sees in

person.

Key Accountabilities

• Run the North American estate. Own availability incidents changes and service levels across retail ERP POS order management e-commerce wholesale and EDI warehouse and DC systems finance interfaces infrastructure and service desk. Peak trading store openings and DC go-lives never slip because of technology.
• Modernise the stack end to end. Deliver a gated roadmap that retires the legacy ERP and AS400-era core replaces point-to-point interfaces with API and event-based integration lands data in Snowflake exits the data center to cloud and upgrades store and DC technology. Progress is measured by what was switched off.
• Be hands on. Review architecture and code design key integrations yourself and join the incidents that count. Use AI-assisted delivery to multiply a small team and prove it with numbers.
• Lead the team on the ground. Line manage the MIS team across applications infrastructure and support. Set standards raise capability hire and exit where needed and build a team that engineers rather than forwards tickets to vendors.
• Own the North American vendor and contractor estate. Manage outsourcing and contractor relationships: SOWs performance criticality and exit terms. Bring critical knowledge in house and run transitions with the Director of Delivery without a drop in service.
• Converge with the global platform do not fork it. Work with the CIO on one global architecture set of standards and security posture. Lead the North American side of the unification programme including Office Salesforce Commerce Cloud Workday OneStream and the Kentucky DC automation. Regional deviations need a case and a sign-off.
• Keep it secure and auditable. Own SOX IT general controls PCI and the security baseline with the CISO. Findings get closed not re-reported.
• Be the single voice on technology for North America. One roadmap budget and set of numbers for North America and Lugano reported through the delivery Center of Excellence in the same way as other units.

Candidate Profile

Essential requirements

• Twelve or more years in technology at least five leading a technology function in a multi-site US retail wholesale or consumer goods business; fashion or apparel strongly preferred.
• Has personally led an end-to-end modernisation of a legacy estate while the business kept trading with measurable results: systems retired cost removed incidents reduced lead time improved.
• Still technical: reviews code and architecture has recently designed integrations and data flows and knows API event and cloud patterns well enough to challenge a vendor and run an incident bridge.
• Has line-managed a mixed team of employees and contractors including hiring exits and capability building.
• Has managed a large vendor and contractor estate including SOWs performance management and bringing knowledge in house.
• Deep retail systems knowledge: ERP POS order management warehouse and DC systems e-commerce wholesale and EDI and the finance interfaces between them.
• Based in or relocating to Los Angeles on site at HQ with regular travel to Kentucky and Lugano and several days a week overlapping European hours.

Preferred qualifications

• AI-assisted delivery on a legacy estate (coding agents AI-generated specifications and tests) with quantified results.
• Led a data center exit or cloud migration end to end on Azure or AWS including security networking and cost model.
• Exposure to the Guess estate: Salesforce Commerce Cloud retail ERP and POS order management PLM and planning warehouse management DC automation Workday OneStream Snowflake and MicroStrategy.
• Working knowledge of SOX IT general controls and PCI DSS in a retail environment.

Working style

• Hands on. You would rather look at the system than the status report and you can do the work you ask of the team.
• Direct. You say what the data says early to the people it affects.
• Owner. North America is your estate; nothing in it is somebody elses problem.
• Structured. You bring a roadmap scorecard and budget and make the estate legible to non-technical people.
• Low ego high standards. You work through the CIOs architecture and the Center of Excellences gates and build people rather than rely on heroes.

Key Challenges

The risks are familiar: modernisation stays a slide while the legacy core depends on a few people; contractors hold the knowledge; North America duplicates the global platform; the data center exit stalls at cutover; peak trading becomes a standing excuse for no change; or you fight Lugano for autonomy instead of converging and delivering. If you have spent recent years approving others architectures from a distance this is not that interview we will ask for the last legacy system you personally retired what broke and what it cost.

Assessment Criteria

1. COMPETENCY: Modernisation delivered end to end

WEIGHT: 25%

EVIDENCE W E WILL ASK FOR: A legacy platform you retired or re-platformed while trading: the sequence what broke cost and timeline versus plan and lessons learned.

2. COMPETENCY: Hands-on technical depth

WEIGHT: 20%

EVIDENCE W E WILL ASK FOR: An architecture or integration you designed in the last two years. You will work a real Guess problem in the interview.

3. COMPETENCY: Running the estate

WEIGHT: 15%

EVIDENCE W E WILL ASK FOR: Availability incident and change data from an estate run through peak; your worst outage its root cause and what changed.

4. COMPETENCY: Team leadership on the ground

WEIGHT: 15%

EVIDENCE W E WILL ASK FOR: A team you inherited: who you kept and exited how you raised the bar and the evidence.

5. COMPETENCY: Vendor and contractor management

WEIGHT: 15%

EVIDENCE W E WILL ASK FOR: A contractor estate you reduced: knowledge brought in house SOW and exit terms used savings realised versus planned.

6. COMPETENCY: AI-assisted delivery literacy

WEIGHT: 10%

EVIDENCE W E WILL ASK FOR: Coding agents and AI-generated specifications or tests used on a legacy estate with numbers including where they did not pay off.