Director Technology Strategy Jobs in Reston, VA (NOW HIRING)

Position Overview

Tuckernuck is looking for an experienced, customer-centric, Technology Delivery and Operations Director to ensure our technology work is executed predictably and our day to day technology operations run reliably. This role owns the operating rhythm for delivery across cross functional initiatives and serves as the coordination point for technology operations. They monitor critical integrations, coordinate maintenance windows and releases, manage incident response and escalation, and drive clear communication and documentation. You will partner closely with internal teams and external vendors to reduce operational drag and keep business critical systems healthy as we scale and foster a transparent and collaborative culture.

Core Responsibilities

• Own the delivery operating model across technology initiatives, including intake, prioritization support, planning cadence, status reporting, and dependency management.
• Drive predictable execution of cross functional initiatives by coordinating internal teams and external vendors, with clear owners, timelines, and definitions of done.
• Maintain a single view of delivery health across active work, with weekly updates for stakeholders.
• Monitor critical integrations and scheduled jobs. Triage failures and escalate to the correct technical owner or vendor with clear context and business impact.
• Own incident management for technology issues, including severity definitions, incident coordination, stakeholder communications, and post incident retrospectives that produce continuous improvements.
• Coordinate maintenance windows and releases across internal systems and third party platforms, including change planning, approvals, communications, and rollback plans.
• Eliminate root causes of recurring issues by tracking trends and communicating action items that need to be completed.
• Collaborate closely with cross-functional teams, including finance, planning, operations, and ecommerce to ensure that all business objectives are achieved
• Creates project plans, makes changes as necessary and effectively communicates status and issues to stakeholders.
• Own technology change management processes, including release calendars, reviews of high risk changes, communication plans, and post release verifications.
• Run post implementation and post incident retrospectives to convert lessons learned into specific improvements that are assigned to internal teams and external vendors.
• Build and maintain operational documentation, including runbooks, escalation paths, maintenance calendars, and a knowledge base that reduces repeat work and improves transparency.
• Actively learns, exploring areas and skills that will help Tuckernuck continue to grow.

Minimum Qualifications

• At least 10 years 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 successfully managing and delivering complex technical projects or programs, ideally within a fast-paced environment.
• Strong understanding of modern delivery practices (Agile and iterative execution), integration patterns, and operational disciplines (incident management, change management, 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 a keen attention to detail.
• Comfort working with ambiguity while driving clarity on ownership, sequencing, and decisions.

Knowledge/Skills/Abilities

• Exceptional delivery management skills with demonstrated complex launches, high attention to detail and situational fluency, ability to influence and motivate others, and perseverance to handle challenging business situations and assess trade-offs.

• Exceptional analytical, critical thinking, and strategic problem-solving skills, with the ability to deal with ambiguity and cut through complexity, turning high-level business requirements and opportunities into specific project deliverables.
• Exceptional verbal and written communication and data presentation skills, including an ability to effectively communicate with both business and technical teams.
• Detail-oriented, deadline-driven, and well versed in technical project management
• Experience guiding cross-functional teams, with the ability to interact with stakeholders at all seniority levels.
• Must have strong communication skills.
• Must be able to grow and cultivate strong working relationships with key vendors in order to help scale the business.
• Be an active team player and believe that no task is too small for the benefit of the greater good.

Compensation

Compensation for the role will be determined based on the candidate's qualifications, skills, and experience. The estimated annual compensation for this role is $140,000-$170,000; classified as full-time exempt and not eligible for overtime. At Tuckernuck, we care about our team and offer benefits that support your health, growth, and work-life balance. This includes medical, dental, and vision coverage, a 401(k) with a company match, generous paid time off and holiday, paid new parent leave, a generous employee discount, and other great perks.

Tuckernuck Core Values
The successful candidate will also demonstrate the following core values that inspire the Tuckernuck team to make a difference.

• Teamwork Makes the Dream Work
• Find the Fun
• Stay Authentic
• Respect
• Entrepreneurial Spirit
• Start Strong & Finish Strong
• Have Courage

Tuckernuck is an equal opportunity employer and makes employment decisions on the basis of merit. Tuckernuck policy prohibits unlawful discrimination based on race, color, religious creed, sex, gender identity, marital or veteran status, age, national origin, ancestry, citizenship, physical or mental disability, medical condition, genetic information or characteristics (or those of a family member), sexual orientation, pregnancy, or any other consideration made unlawful by federal, state, or local laws. It also prohibits discrimination based on a perception that anyone has any of those characteristics or is associated with a person who has or is perceived as having any of those characteristics. All such discrimination is unlawful.