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Agent guide: [/agents.md](https://www.wearedevelopers.com/agents.md). --- # Senior Director, Technology Leader - **Company:** Independence, Inc. - **Location:** Chicago, IL, United States - **Experience:** Expert - **Salary:** $172,103.0 - $252,008.0 - **Contract:** Permanent contract - **Skills:** Agile Methodology, Generative AI, Information Technology - **Published:** October 7, 2026 - **Apply:** https://www.indeed.com/viewjob?jk=7aa0c53462b3975e ## About the Role * Forward-thinking strategist skilled in devising and operationalizing a technology strategy across multiple operating entities * A storyteller who translates technical concepts into business terms and articulates the value of technology investments to stakeholders * Commitment to upholding the highest standards of integrity and accountability in managing the organization's technology * Flexible and adaptable to respond to evolving technology challenges and organizational needs * A change agent that fosters a culture of innovation and continuous improvement, encouraging experimentation, and adapting to evolving circumstances and environment * An authentic and tenacious leader who leans in to partnering with peers and is a collaborative team leader who is steadfast in leading by example * Exemplary organizational skills coupled with proactive initiative-taking meticulous attention to detail, and adept time management, flourishing in a dynamic and rapidly evolving environment * Acts as a culture ambassador, living our organizational values * Experience Managing Onshore and Offshore Teams: Proven ability to lead and manage both onshore and offshore teams, ensuring seamless collaboration and execution of technology projects. This includes strategic oversight, cross-cultural leadership, communication and coordination, performance management, resource allocation, and risk management. Education and Experience: * Proven experience 15+ years in project management, strategy, communication, and operations in a technology-driven global organizations * Experience driving internal development teams and external partners to deliver business outcomes using agile methodologies * Strong understanding of technology project lifecycles, portfolio management, and best practices in delivering large-scale technology initiatives * Strong understanding of financial management, including budgeting, ROI analysis, and investment prioritization for technology projects. * Experience with vendor management in an outsourced or managed service environment * Experience with M&A or PE environment is desirable * Exceptional analytical skills, with the ability to track and report on roadmaps, business cases, and ROI * Strong leadership with the ability to influence and collaborate with cross-functional teams across different geographical locations * Excellent communication skills, with the ability to effectively present complex information to senior executives and stakeholders * Bachelor's degree in computer science, Engineering, Business Administration, or a related field Other: Limited US travel to major hubs is required. ## Description The Senior Director will lead a multi-brand business unit to drive consolidated roadmaps, tracking, budget, and delivery of all technology projects. This role will work closely with senior leadership to: * Align technology execution to business outcomes * Driving roadmaps including moving environments onto a companywide standard * Own communication and change management for large initiatives * Ensure that key initiatives are prioritized, executed, and ROI measured effectively * Tracking project progress and financials against approved roadmap * This role requires the ability to collaborate with and influence multiple stakeholders to develop and deploy robust enterprise-wide technology projects to meet long term business goals. The Senior Director plays a pivotal role in driving the organization's technology strategy and ensuring alignment with business goals. This is an exciting opportunity for a seasoned strategic leader to influence the long-term direction of technology at a high level while working closely with executive leadership to achieve business success. Focus areas: * Technology Excellence- Exemplify the organization's commitment to excellence, building trust and credibility among stakeholders and customers * Transformation Enabler - Foster a culture of experimentation and collaboration within the organization, driving continuous improvement, agility, and competitive advantage in with a cost effective and reliable environment leveraging Gen AI and automation * Capability Builder - Support the organization's technological needs by delivering holistic roadmaps to deliver the required ROI * Customer Champion - Prioritize customer-centric technology projects and track the appropriate ROI, Strategic Leadership & Vision: * Partner with technology leadership and other executives to define and communicate the long-term technology roadmaps aligned with the company's business goals and market opportunities * Lead planning efforts to ensure that technology investments are future-proof, scalable, and capable of supporting business growth and transformation * Identify emerging technologies and industry trends, advising leadership on their potential impact on the business and shaping the organization's technology roadmap * Technology Roadmap & Planning: * Develop and maintain comprehensive, technology road maps that align with both current and future business needs * Drive the planning and prioritization of key technology initiatives across the organization, ensuring that resources are optimally allocated and aligned with strategic goals * Work with business units to understand their strategic objectives and translate those into actionable technological plans and solutions Portfolio Management: * Oversee the portfolio of technology projects, ensuring alignment with business outcomes and proper resource allocation * Evaluate project performance, track key performance indicators (KPIs), and adjust course as necessary to ensure timely delivery and alignment with overall strategy * Identify risks within the portfolio and collaborate with project managers and business leaders to mitigate or resolve issues * Cross-functional Collaboration: * Foster close collaboration between the technology team and other business units (e.g., Product, Operations, Marketing, Sales) to ensure alignment and successful execution of technology initiatives * Act as a liaison between technical and non-technical teams, ensuring clear communication of technology strategy and priorities to senior business leaders * Drive integration of technological initiatives across the business, ensuring that systems and processes work cohesively to support overall business objectives Financial Management: * Work closely with Procurement and Finance team to develop and manage the technology budget, ensuring effective allocation of resources to strategic priorities * Analyze the financial impact of technology initiatives, providing recommendations on investment and cost optimization strategies. * Ensure the effective management of technology investments to deliver maximum return on investment (ROI) * Metrics & Reporting: * Develop a set of key metrics and performance indicators to track the progress and success of technology initiatives and investments * Provide regular strategic updates to the CTO, executive leadership, and other stakeholders, using data and analytics to communicate progress, risks, and outcomes * Use insights from reporting and metrics to refine strategy and drive continuous improvement across the organization * Mergers & Acquisitions (M&A) Strategy: * Support the CTO and leadership team in M&A activities by evaluating potential technology synergies, assessing integration opportunities, and providing strategic guidance on technology-related aspects of acquisitions * Lead the development of integration plans that align acquired technologies with the broader organizational strategy Communication and Change Management: * Lead change management activities required to roll out and adopt technology projects to ensure effective return on investment * Drive communication to ensure stakeholders across the portfolio of companies are kept aware of the latest developments and buy into the technology project impacts