Top Tech Jobs & Startup Jobs in Chicago, IL

Lead strategy and operating model for bookkeeping, payroll, and tax services. Drive automation and AI adoption, establish scalable workflows and KPIs, grow and mentor a 25+ person team, and partner cross-functionally to align product, fintech, and go-to-market for seamless, compliant financial service delivery.

The Account Executive is responsible for onboarding service professionals to Housecall Pro, providing tailored solutions, delivering product demos, and ensuring great customer service throughout the sales process.

The Vertical Vice President, Technology drives engineering execution, operational excellence, and organizational capability across the Wedding & Events Vertical. Responsibilities include overseeing engineering teams, improving platform reliability, and implementing AI-enabled practices for enhanced productivity and product innovation.

Lead technical authority for the enterprise IAM program: define roadmap and architecture, manage Okta and Entra ID configurations and federation, build automated provisioning/deprovisioning (UKG integration), enforce RBAC and Zero Trust controls, drive audits/compliance, mentor IAM engineers, and integrate identity solutions across security, infrastructure, and application teams.

Manage control accounts for defense space programs through planning, budgeting, forecasting, EVM processes, performance analysis, IMS and baseline management, risk and RIO tracking, subcontractor coordination, compliance support, and executive reporting to ensure programs meet cost, schedule, and technical objectives.

Enable, optimize, and sustain operational systems and workflows by gathering requirements, configuring and supporting SharePoint and Power Platform solutions, troubleshooting issues, supporting testing and UAT, developing reports and dashboards, creating documentation and training materials, and driving continuous improvement and governance compliance.

Support finance team with monthly close tasks, accounts payable administration, cash and credit card reconciliations, weekly cash flow reporting, audit support, customer and vendor setup, payroll information requests, and ad hoc accounting documentation and reporting.

Lead and scale a ~25-person EHR implementation and client services organization, owning end-to-end EHR integrations (Epic, Cerner, Meditech), operating model, processes, governance, and executive client engagement to ensure successful order/result workflows, interoperability, and post-launch support.

Lead and execute B2B marketing initiatives: define brand strategy, redesign website, create sales collateral, manage social media and conferences, produce videos, and coordinate with agencies and leadership to target defense buyers.

Perform data collection, cleaning, validation, and analysis on large client datasets using Python, SQL, and spreadsheets. Produce actionable insights and business narratives, automate data workflows, and support text/document annotation to generate labeled data for NLP and LLM solutions. Collaborate with senior analysts and improve internal analytical processes and tool configurations.

Manage a book of MSP partner accounts with high-volume outbound activity, build partner relationships, drive joint sales and marketing motions, increase partner program status, and ensure strong renewals and retention.