Director, Technology Delivery & Operations

Tuckernuck Inc• US,

13h•$140,000 - $170,000

About The Position

Tuckernuck is seeking an experienced, customer-centric Technology Delivery and Operations Director to ensure technology work is executed predictably and day-to-day technology operations run reliably. The role owns the operating rhythm for delivery across cross-functional initiatives and coordinates technology operations. Responsibilities include monitoring critical integrations, coordinating maintenance windows and releases, managing incident response and escalation, and driving clear communication and documentation. The Director partners with internal teams and external vendors to reduce operational friction and keep business-critical systems healthy as the company scales, while fostering a transparent and collaborative culture. The successful candidate will demonstrate Tuckernuck’s core values: teamwork, finding the fun, authenticity, respect, entrepreneurial spirit, starting strong and finishing strong, courage, and continuous improvement. Tuckernuck is an equal opportunity employer and makes employment decisions on the basis of merit.

Requirements

At least 10 years of experience in technology delivery, technical program management, technology operations, or service delivery, with demonstrated ownership of cross-functional execution.
Experience supporting business-critical retail workflows across ecommerce, OMS/ERP, WMS/3PL, payments, or data integrations in a fast-paced environment.
Proven track record of managing and delivering complex technical projects or programs.
Strong understanding of modern delivery practices, including Agile and iterative execution, integration patterns, and operational disciplines such as incident management, change management, and monitoring.
Excellent leadership, communication, and interpersonal skills, with the ability to influence and collaborate with cross-functional teams at all levels.
Exceptional problem-solving and critical-thinking abilities, with strong attention to detail.
Comfort working with ambiguity while bringing clarity to ownership, sequencing, and decisions.
Exceptional delivery management skills, including experience with complex launches, situational fluency, influencing and motivating others, perseverance in challenging business situations, and assessing trade-offs.
Exceptional analytical, critical-thinking, and strategic problem-solving skills; ability to navigate ambiguity and complexity and translate high-level business requirements and opportunities into specific project deliverables.
Exceptional verbal and written communication and data presentation skills, including the ability to communicate effectively with business and technical teams.
Detail-oriented, deadline-driven, and well versed in technical project management.
Experience guiding cross-functional teams and interacting with stakeholders at all seniority levels.
Strong communication skills.
Ability to be an active team player and support the greater good, with the belief that no task is too small.

Responsibilities

Own the delivery operating model for technology initiatives, including intake, prioritization support, planning cadence, status reporting, and dependency management.
Coordinate internal teams and external vendors to deliver cross-functional initiatives predictably, with clear owners, timelines, and definitions of done.
Maintain a consolidated view of delivery health across active work and provide weekly stakeholder updates.
Monitor critical integrations and scheduled jobs; triage failures and escalate them to the appropriate technical owner or vendor with relevant context and business impact.
Own technology incident management, including severity definitions, incident coordination, stakeholder communications, and post-incident retrospectives.
Coordinate maintenance windows and releases across internal systems and third-party platforms, including change planning, approvals, communications, and rollback plans.
Track recurring issue trends, communicate required action items, and drive elimination of root causes.
Collaborate with finance, planning, operations, ecommerce, and other cross-functional teams to achieve business objectives.
Create and update project plans and communicate project status and issues to stakeholders.
Own technology change management processes, including release calendars, reviews of high-risk changes, communication plans, and post-release verification.
Run post-implementation and post-incident retrospectives and turn lessons learned into assigned improvements for internal teams and external vendors.
Build and maintain operational documentation, including runbooks, escalation paths, maintenance calendars, and a knowledge base.
Continue learning and exploring areas and skills that can help Tuckernuck grow.
Cultivate strong working relationships with key vendors to help scale the business.
Contribute as an active team player and take on tasks for the benefit of the greater good.