Top Tech Jobs & Startup Jobs in Chicago, IL

Conduct outbound prospecting through calls, emails, and LinkedIn; engage qualified public-sector buyers using AI-driven insights; book demos; optimize messaging; and help build the company’s outbound sales playbook. The role includes structured training, mentorship, and a pathway to Account Executive.

Manage and coach a four-person BDR team while remaining hands-on with outbound sales. Own qualified meeting generation, pipeline health, forecasting, reporting, messaging, sequences, target account research, and performance metrics. Partner with Sales, Marketing, and RevOps to improve top-of-funnel results through coaching, A/B testing, playbook development, hiring, onboarding, and rep ramping. The role also requires familiarity with technical or cloud infrastructure buyers and FinOps, DevOps, or cloud technologies.

Join Arootah's advisor network to provide fractional Chief AI Officer / AI Strategy leadership to hedge funds, private equity firms, and family offices. Advise on AI initiatives, strategy, governance, vendor evaluation, workflow automation, change management, and implementation roadmaps. Engage on project-based assignments; client origination handled by Arootah.

Architect and build backend systems powering conversational AI experiences. Lead complex projects across the software development lifecycle, define technical direction, design scalable solutions, and ensure system quality. Mentor engineers through code reviews, knowledge sharing, and onboarding while collaborating cross-functionally on product strategy, experiments, and high-value initiatives. Develop LLM-driven infrastructure and maintain operational excellence across production systems.

Oversee company financial operations, including accounts payable and receivable, budgeting, forecasting, cash flow monitoring, financial reporting, and regulatory compliance. Coordinate with external auditors and tax consultants, prepare management reports, and ensure adherence to accounting standards and requirements.

Provide technical assistance to develop and implement a sustainable school feeding program in Dire Dawa. Responsibilities include stakeholder engagement, government coordination, operational and policy framework development, monitoring and evaluation design, data governance, risk management, systems mapping, capacity building, and sustainability planning. The consultant will facilitate workshops, advise on Ethiopia’s political and institutional context, coordinate stakeholders, and produce work plans, progress reports, data governance recommendations, and a final assignment report.

Own DBS end-to-end across the consumer hotel booking journey, hotel-facing onboarding and reporting workflows, and search and AI discovery capabilities. Define product vision, roadmap, user journeys, success metrics, and experiments; conduct customer research and usability testing; improve booking conversion and hotel adoption; and align Engineering, Design, Sales, Marketing, and Customer Success around measurable product outcomes.

Lead the onboarding and implementation of new clients for iCareManager, managing projects, conducting training, and ensuring client satisfaction throughout the process.

Own customer onboarding and product support for CAM Assist. Personally guide new customers from sales handoff through installation, setup, and first accepted toolpath, while managing the support queue and developing the support specialist. Build scalable playbooks, help content, knowledge systems, and product feedback loops; monitor usage, prevent onboarding stalls, manage escalations, and improve time-to-value for manufacturing customers.

Leads US people strategy and end-to-end HR support across the employee lifecycle for a distributed healthcare AI organization. Advises leaders on performance, employee relations, compliance, benefits, engagement, wellbeing, and capability development. Partners with clinician recruitment and credentialing teams, mentors People Experience colleagues, uses people data to guide decisions, and manages sensitive matters with autonomy across a three-day workweek.