Top Tech Jobs & Startup Jobs in Chicago, IL

Own the full sales cycle for an early-stage AI recruiting platform: prospect, demo, negotiate, close deals, build pipeline, refine outbound strategy with the CEO, represent the company at events, and coordinate handoffs with Customer Success to ensure long-term account health.

Gather and document business and user requirements, define system scope, suggest workflow improvements, modify/test/implement third-party software or scripts, lead small-to-mid projects, fully document requirements/testing/code/processes, and mentor Associate Systems Analysts.

Outside enterprise sales role responsible for net-new business development, prospecting, pipeline management, partner/channel sales, closing deals, and tracking activity in Salesforce. Frequent travel and territory/territory management, partner enablement, trade show attendance, and competitive positioning are required.

Execute and optimize multi-channel CRM campaigns (email, push, SMS, in-app) using marketing automation platforms. Manage audience segmentation, QA, deployment, A/B testing, reporting, and data integrations. Collaborate cross-functionally to improve targeting, personalization, and lifecycle performance using analytics and AI-driven tools.

Manage and optimize full-funnel digital advertising across multiple self-serve platforms, analyze performance and cohorts, create and test ad creative and landing pages, support website and listings improvements, coordinate sponsor/IRB creative approvals, and recommend new digital trends to grow recruitment and conversions.

Lead U.S. revenue generation and manage a distributed cybersecurity sales organization. Drive pipeline, forecasting, territory and account strategies; coach and hire sales staff; engage strategic enterprise accounts and C-level stakeholders; support complex negotiations; collaborate with marketing, delivery, finance and services; maintain Salesforce hygiene and KPI-driven forecasting; represent the company at industry events.

Generate and qualify inbound and outbound leads, build pipeline through prospect research and outreach (phone, email, LinkedIn), set qualified meetings, maintain Salesforce records, collaborate with AEs and marketing, meet activity and pipeline targets, and represent the company professionally.

Lead design and implementation of AWS-native, event-driven microservices using Kafka/MSK and WebSockets. Build CI/CD and IaC pipelines (Terraform, Jenkins, Packer), containerize with Docker/Kubernetes, implement observability (Prometheus, Grafana, ELK), and ensure secure, resilient architectures following DevSecOps and VA standards while mentoring engineers.

Execute inbound and outbound prospecting to qualify leads, book meetings, and grow pipeline. Use phone, email, LinkedIn, live chat and sales tools (Salesforce, Gong, ZoomInfo) to manage contacts, collaborate with sales executives and marketing, and support regional revenue goals while developing sales skills.

Lead the design and delivery of AI-enabled revenue workflows: analyze funnel and pipeline data, identify automation and AI opportunities, build/configure automations and copilots, partner with Sales/Marketing/Technology to deploy scalable, measured revenue operations improvements.