Top Tech Jobs & Startup Jobs in Chicago, IL

Leads complex Workday HCM integration workstreams from discovery through deployment and go-live. Responsibilities include requirements discovery, solution design, integration development, testing, risk and dependency management, customer guidance, technical strategy, mentoring consultants, and quality oversight. The role also applies approved AI and automation capabilities to improve delivery while protecting customer data. Candidates need enterprise integration and customer-facing consulting experience, technical expertise in APIs and data transformation, programming or scripting skills, and familiarity with AI and LLM-based applications.

Drive net-new enterprise customer acquisition for Workday by developing territory and account strategies, coordinating with pre-sales and internal teams, managing long sales cycles, negotiating with C-suite stakeholders, and maintaining accurate pipeline and forecast data to close deals—particularly around core financials and enterprise cloud ERP/HCM solutions.

Own services strategy and quota-bearing services sales for enterprise Financial Services accounts. Lead discovery, scoping, implementation roadmap design, effort and cost estimation, proposals, statements of work, deal negotiation, and deployment risk coordination. Partner with account teams, pre-sales, implementation partners, Global Services, and Customer Experience to support subscription sales, services adoption, successful implementations, and long-term customer value.

Provides technical Workday integration consulting to customers after go-live. Responsibilities include researching customer questions, troubleshooting and optimizing configurations, delivering demonstrations, presentations, workshops, feature adoption guidance, configuration reviews, integration optimization, and feature deployments. The consultant serves as a trusted Workday advisor, maintains certifications and product expertise, supports customer decision-making, and helps create programs that improve feature adoption. Travel may be required up to 20%.

Leads joint business development with financial services partners, generating pipeline and bookings aligned with Workday’s sales organization. Builds partner plans, manages campaigns and sales plays, identifies opportunities, and coordinates forecasting, pipeline management, and deal execution. Collaborates across sales, marketing, services, legal, pre-sales, and partner teams while influencing matrixed organizations and driving go-to-market execution. Requires strong partner sales experience, financial services expertise, executive presence, and moderate travel.

The Senior Engagement Manager leads large and complex global Workday deployments, applying Workday’s deployment methodology and resolving complex implementation issues. The role manages customer relationships, executive expectations, issue resolution, and deployment outcomes across HCM, Payroll, Financials, and related enterprise applications. The manager also provides recommendations to improve deployment practices, communicates with senior stakeholders, influences decision-makers, and may travel up to 30%.

Leads the global Digital Value Management team, owning digital tooling strategy, AI-assisted value experiences, data and benchmarking, technology partnerships, and roadmap execution. The role scales self-service business-case and outcome tooling across global go-to-market motions, drives adoption and revenue impact, manages budgets, and advises executives. It also develops people leaders, aligns Solution Consulting, Customer Success, Sales, Revenue Operations, and Business Technology, and shapes how digital experiences support the customer journey.

Develops financial product demonstration solutions, supports strategic sales opportunities, and designs Workday Financials solutions for customers. Collaborates with development, product strategy, professional services, and solution consulting teams; influences product roadmaps; maintains demo environments; shares product methodologies; and tracks industry trends. The role requires deep financial accounting knowledge, ERP implementation experience, Workday or competing financial application experience, and periodic travel.

Designs the strategy and operating framework for AI-driven demand generation and outbound prospecting. Translates business needs into functional requirements, system logic, governance guardrails, and decision trees for technical teams. Partners with Sales, SDR, Marketing, Product, and analytics leaders to align initiatives with pipeline and revenue goals. Monitors GTM AI trends, evaluates prospecting effectiveness, and recommends improvements based on conversion and performance metrics.

Own the technical onboarding and readiness of Wellness Partners—leading API integration onboarding, authentication and test-tenant setup, test-case development, and validation. Build training, documentation, and a partner certification program. Coach partners through deployment phases, provide technical advisory and hands-on tenant configuration when needed, and create playbooks and toolkits to enable repeatable, scalable customer implementations while minimizing time-to-deploy.