Overall PurposeWe are seeking a collaborative, forward-thinking technology leader to guide our digital evolution and help scale our organization over the next 3–5 years. The Head of Technology & Digital Strategy will provide strategic and operational leadership across all aspects of technology. This role was created to elevate technology as a key enabler of organizational growth, innovation, and operational excellence. Reporting to the CFO and working closely with the senior leadership team, the successful candidate will lead the development and execution of a comprehensive IT roadmap, oversee core systems and vendor partnerships, and ensure that our technology infrastructure supports both our mission and long‑term sustainability.This is a leadership role for someone who can balance strategy and execution — building consensus, driving projects forward, and delivering meaningful results in a collaborative, mission‑driven environment.Key AccountabilitiesStrategy and Planning: (40%)Spearhead the development, execution, and ongoing monitoring of comprehensive, forward‑looking plans for all IT endeavors in close collaboration with the CFO and senior management.Translate business requirements into scalable system solutions, leveraging cutting‑edge tools and architectures while ensuring long‑term viability and adaptability.Drive the evolution of our technology infrastructure to underpin key business strategies and processes, fostering scalability and agility.Oversee an IT Innovation Committee, tasked with execution of the technology strategic plan, in addition to defining policies and controls that synchronize IT activities with organizational goals, ensuring robust risk management, regulatory compliance, and optimal resource allocation.Champion cross‑functional collaboration to conceptualize, develop, and deploy technology solutions that drive organizational growth and operational efficiency.Cultivate a culture of innovation and continuous improvement across all facets of the organization, inspiring teams to push boundaries and explore new frontiers.Project Management: (30%)Develop and execute meticulous project plans to seamlessly integrate new technologies, encompassing robust change management and comprehensive training initiatives.Oversee the end‑to‑end process of RFP,



vendor selection, contract negotiation, and budget oversight for all technology projects, ensuring alignment with strategic objectives and fiscal prudence.Oversee performance and optimization of third‑party IT services.Risk Management and Compliance: (20%)Safeguard the company's operations against a spectrum of IT risks, including data breaches, integrity issues, system failures, and service disruptions.Proactively identify, evaluate, and mitigate emerging IT risks in alignment with enterprise risk management protocols, fostering a culture of resilience and preparedness.Develop and maintain robust IT business continuity and disaster recovery plans, ensuring organizational resilience in the face of adversity.Ensure adherence to governmental regulations and industry standards pertaining to IT services, encompassing areas such as data privacy, accessibility, and security.People Management: (10%)Provide strategic direction and oversight to a multidisciplinary team, aligning departmental activities with overarching strategic imperatives.Facilitate regular departmental meetings, setting clear agendas and delineating responsibilities to drive progress and accountability.Collaborate with HR in all aspects of the talent lifecycle, from recruitment and selection to onboarding and career development.Foster a culture of continuous learning and growth, coaching and mentoring staff to reach their full potential.Conduct regular performance evaluations and goal‑setting sessions, documenting and addressing achievements and areas of improvement.Cultivate a positive workplace culture characterized by inclusivity, collaboration, and employee well‑being, driving employee engagement and retention.Champion initiatives that promote employee wellness and safety,



fostering a conducive work environment that supports individual and collective flourishing.Perform other duties and responsibilities as assigned by the Manager or designate.Current Technology EnvironmentBlackbaud: Raiser’s Edge, Financial EdgeMicrosoft environment (SharePoint recently transitioned)Engaging Networks (fundraising adjacent platform)ADP (HR/payroll)No data lake currentlyEarly data roadmap underwayOpportunity: Build scalable data & systems architecture on Microsoft foundation.Immediate Priorities (First 12 Months)Strengthen MSP oversight (TechaFY)Stabilize and optimize foundational systemsInfluence and refine early‑stage IT roadmap (in development)Drive data strategy discussions (possible ERP implementation)Ensure SharePoint transition continues smoothlyAdditional Skills & QualificationsClear, direct communicator (“clarity is kindness”)Collaborative leaderSomeone comfortable in a warm, people‑first environmentAdaptable and hands‑on when neededExperience with fundraising operations and related software as well as camp management software (NICE TO HAVE)Experience in Web ManagementCurrent driver’s license and the ability to be covered by camp’s insurance policy.A collaborative leader who builds trust and alignment across teamsComfortable balancing big‑picture thinking with hands‑on executionMission‑driven and motivated by purposeDirect, respectful communicator who believes clarity drives progressAdaptable and comfortable working in a energetic, people‑first organizationEnthusiastic, accurate, detail oriented, service oriented, excellent time‑management and organizational skills, flexible, diplomatic, discreet, excellent oral and written communication, able to meet deadlines and work well under stress, analytical, problem‑solving skills, sense of fiscal responsibility, able to work independently and with a team.Experience LevelExpert LevelJob Type & LocationPermanent position based out of Toronto, ON.Pay And BenefitsPay range: $140,000.00 - $180,000.00 per year.Workplace TypeHybrid position in Toronto, ON.The company is an equal opportunity employer and will consider all applications without regard to race, sex, age, color, religion, national origin, veteran status, disability, sexual orientation, gender identity, genetic information or any characteristic protected by law.#J-18808-Ljbffr

📌 Senior Director, Technology & Digital Transformation - C$140,000 - C$180,000 A Year (Toronto)
🏢 TEKsystems
📍 Toronto