Director, Technology Procurement & Strategic Sourcing (Chicago)

The Aspen Group (TAG) is one of the largest and most trusted retail healthcare business support organizations in the U.S. and has supported over 20,000 healthcare professionals and team members with close to 1,500 health and wellness offices across 48 states in four distinct categories: dental care, urgent care, medical aesthetics, and animal health. Working in partnership with independent practice owners and clinicians, the team is united by a single purpose: to prove that healthcare can be better and smarter for everyone. TAG provides a comprehensive suite of centralized business support services that power the impact of five consumer-facing businesses: Aspen Dental, ClearChoice Dental Implant Centers, WellNow Urgent Care, Chapter Aesthetic Studio, and Lovet. Each brand has access to a deep community of experts, tools and resources to grow their practices, and an unwavering commitment to delivering high-quality consumer healthcare experiences at scale.As a reflection of our current needs and planned growth we are very pleased to offer an opportunity to join our dedicated team as a Director, Technology Procurement & Strategic Sourcing.At The Aspen Group, we recognize that strategic supplier partnerships, technology innovation, and disciplined procurement governance are critical to enabling scalable growth and delivering exceptional support to the practices we serve nationwide. The Director of Technology Procurement & Strategic Sourcing will lead over $100M in enterprise-wide sourcing strategy and supplier management initiatives across an increasingly complex technology portfolio for an innovation focused organization in spend categories including Enterprise and Clinical SaaS, AI & Emerging Technologies, IT Professional Services, Telecom, Infrastructure, Hardware, Security, and Contact Center Technologies. This leader will serve as a trusted advisor to executive stakeholders, driving enterprise value through strategic sourcing, supplier innovation, operational efficiency, risk mitigation, and financial optimization.The Director will oversee complex negotiations, lead transformational sourcing initiatives, establish category strategies aligned to corporate objectives, and enhance procurement governance across the organization. This role will partner cross-functionally with Technology, Security, Legal, Finance, Compliance, and Operations leadership to ensure sourcing decisions support TAG’s long-term strategic priorities, innovation roadmap, and financial goals.Key ResponsibilitiesStrategic Leadership & Category ManagementDevelop and execute enterprise-wide technology sourcing and category management strategies that align with TAG’s business objectives, digital transformation initiatives, and long-term growth plans.Serve as the highly visible procurement lead, thought leader, and strategic advisor to executive IT leadership (CIO, SVPs) across Technology, Security, AI, Infrastructure, and Operations functions.Drive enterprise value creation through supplier consolidation, cost optimization, process standardization, innovation partnerships, and risk reduction initiatives.Establish multi-year category roadmaps, sourcing strategies, supplier segmentation models, and performance management frameworks for critical technology spend areas.Identify emerging market trends, supplier innovations, and industry best practices to proactively position TAG for competitive advantage.Sourcing, Negotiations & Supplier GovernanceLead complex, high-value enterprise negotiations for software, cloud services, AI platforms, infrastructure, telecom, hardware, and strategic professional services agreements.Oversee end-to-end sourcing activities including business requirements gathering, market analysis, RF(x) strategy and execution, proposal evaluation, commercial negotiations, contract structuring, and supplier onboarding.Establish governance frameworks and executive-level supplier management processes to ensure supplier accountability, performance, compliance, service quality, and continuous improvement.Partner with Legal, Security, Compliance, and Risk teams to mitigate contractual, cybersecurity, operational, and regulatory risks associated with third-party technology suppliers.Lead strategic supplier business reviews and executive governance meetings with key enterprise partners.Financial & Operational ExcellenceDeliver measurable savings, cost avoidance, and working capital improvements through strategic sourcing initiatives and commercial optimization strategies.Develop and analyze sophisticated financial models, TCO analyses, business cases, and scenario planning to support executive decision-making.Build scalable procurement processes, policies, tools, and analytics capabilities that improve operational efficiency and procurement maturity across the organization.Drive procurement KPI development, spend visibility, supplier performance metrics, and executive reporting.Leadership & Cross-Functional InfluenceLead, mentor, and develop sourcing professionals while fostering a high-performance, collaborative, and customer-focused culture.Influence and align stakeholders across multiple business units and leadership levels to drive consensus and accelerate strategic initiatives.Champion procurement transformation initiatives, change management efforts, and continuous improvement programs across TAG.Provide regular updates and strategic insights to executive leadership regarding sourcing initiatives, supplier performance, market intelligence, contract renewals, and enterprise risk considerations.Key Skills & QualificationsDeep expertise in strategic sourcing, category management, supplier governance, and complex contract negotiations within enterprise technology environments.Strong executive presence with the ability to influence senior leadership and drive alignment across cross-functional stakeholders.Demonstrated success negotiating large-scale enterprise agreements involving SaaS, cloud technologies, AI platforms, infrastructure, telecom, cybersecurity, and IT professional services.Strong commercial acumen with expertise in financial analysis, business case development, and total cost of ownership modeling.Proven ability to lead enterprise-wide procurement transformation initiatives and implement scalable sourcing processes and governance frameworks.Exceptional leadership, communication, negotiation, and relationship management skills.Ability to effectively navigate ambiguity, competing priorities, and fast-paced business environments while driving strategic outcomes.Experience managing supplier risk, compliance, and performance management programs.Advanced proficiency with Microsoft Office Suite, spend analytics tools, e-Sourcing platforms, contract lifecycle management systems, and procurement technologies.Strong analytical, problem-solving, and decision-making capabilities.Education & Experience RequirementsBachelor’s degree in Business Administration, Supply Chain, Finance, Engineering, Information Technology, or related field required.MBA or advanced degree strongly preferred.Professional certifications such as CPSM, CPSD, PMP, Lean Six Sigma, or equivalent preferred.10+ years of progressive strategic sourcing, procurement, supply chain, or technology vendor management experience, including significant experience leading enterprise technology categories.Demonstrated experience leading complex enterprise negotiations and managing strategic supplier relationships in high-growth, fast-paced organizations.Prior people leadership experience with a track record of developing high-performing teams strongly preferred.Salary: 180-200k, plus bonus incentives, with a generous benefits package that includes paid time off, health, dental, vision, and 401(k) savings plan with matchIf you are an applicant residing in California, please view our privacy policy here: CA Privacy PolicySummaryLocation: Chicago, IllinoisType: Full time