Team Leader - Helpdesk

Summary

Join RT², a company offering flexible, cutting-edge retail management solutions, as their Engineering Manager. Lead and mentor an agile team, focusing on data-driven experimentation and innovation. Collaborate with leadership to establish a divisional mission and promote a company culture. Drive team performance in areas like quality and velocity, and coordinate responses to tech incidents. Regularly evaluate team size and structure, and develop short, mid, and long-term key results. Lead hiring decisions, conduct performance reviews, and implement best practices. This role requires 8+ years of progressive experience in IT support and leadership, expertise in managing enterprise-level support systems, and a strategic mindset.

Requirements

• 8+ years of progressive experience in IT support and helpdesk operations, with 5+ years in a leadership or management role
• Proven ability to scale and lead high-performing IT support functions, driving excellence in service delivery, technical support, and end-user experience
• Expertise in managing enterprise-level support systems and tools, including Azure Active Directory, Intune, Office 365, and industry-standard ticketing platforms such as Zendesk, Jira, or Freshservice
• Strategic mindset with experience establishing KPIs, SLAs, and process frameworks to ensure operational efficiency and continuous service improvement
• Deep understanding of ITIL best practices and the ability to implement structured support models while maintaining flexibility for business needs
• Adept at partnering with cross-functional stakeholders, including Security, People Operations, and Engineering, to support organizational growth and compliance needs
• Experienced in leading IT onboarding/offboarding at scale, developing knowledge bases, managing vendor relationships, and overseeing hardware/software asset lifecycle
• Strong communicator and people leader with a focus on team development, operational alignment, and creating a culture of accountability, responsiveness, and service excellence
• Ability to lead through ambiguity, manage change, and inspire support teams to meet the evolving needs of a hybrid or remote-first workforce
• Committed to building inclusive teams that prioritize user empathy, proactive support, and innovation in internal tools and systems

Responsibilities

• Lead and mentor an agile team that leans into data-driven experimentation, innovation, quality, and craftsmanship
• Mentor peer leaders with guidance and direction from the Director, Engineering
• Communicate and promote the culture and mission of the company
• Collaborate with leadership to establish a divisional mission aligned with the company vision
• Promote iterative, thoughtful decision-making within a self-organized team
• Recognize trends affecting delivery goals and support team decisions on short- and long-term resolutions, removing roadblocks when necessary
• Drive performance in areas, such as quality, predictability, flow, and velocity
• Coordinate response and communication of tech incidents to stakeholders
• Recognize trends across tech incidents and ensure true root causes have been identified and fixes implemented
• Stay informed of trends and changes in the broader technology, business, and regulatory landscapes
• Regularly evaluate the teams size, organizational fit, and position and propose changes to improve synergies
• Understand and plan for the product roadmap and maintain awareness of broader technical and business changes impacting the team
• Develop short-, mid-, and long-term key results with the team to achieve team objectives
• Develop and retain talent in alignment with the product team's vision and roadmap
• Lead interviews and discussions regarding hiring decisions for candidates and promotions, pulling in appropriate subject matter experts as required
• Prepare and deliver reviews, compensation adjustments, and promotions
• Identify, implement, and drive adoption of best practices within the leadership community
• Mentor and support team members on any of the above responsibilities

Benefits

• Remote, flexible working options
• Competitive compensation
• Generous STI and LTI provisions
• Health, Dental and Vision Insurance
• Paid Annual Leave
• Paid Sick Leave
• 401K, and more