Top Tech Jobs & Startup Jobs in Chicago, IL

Drive enterprise employer partnerships across a regional territory by owning full sales cycles, building relationships with HR/benefits leaders and brokers, delivering executive presentations and ROI analyses, managing pipeline and forecasts, differentiating Sword on clinical and financial outcomes, and coordinating with clinical and customer success teams for implementation.

Own a portfolio of 20–30 enterprise employer accounts, leading retention, renewals, pricing coordination, executive relationships, and account recovery. Use enrollment, engagement, outcomes, claims, billing, and ROI data to diagnose performance and demonstrate customer value. Build multithreaded relationships, identify renewal risks and cross-functional breakdowns, coordinate internal resolution, and improve member access and engagement. The role operates remotely with travel of up to 15%.

Perform outbound calls to qualified leads, convert them to Sword Health members, guide enrollment, address objections with proven closing techniques, provide empathetic phone support, collaborate with physical therapists and customer service, and use tools (Zoom Workplace, Excel, Jira, Slack, Notion) and AI to manage outreach and optimize processes.

Lead and build Swords Security Operations Center: architect SIEM, develop detection-as-code, run incident response, mentor SOC engineers, design SOAR/AI automation, run threat hunting and metrics to reduce MTTD/MTTR and scale defenses across cloud environments.

Lead design and improvement of detection, alerting, incident response playbooks, and threat hunting. Drive investigations, digital forensics, AI-assisted automation, and cross-functional coordination to contain, eradicate, and prevent security incidents while measuring and improving SOC effectiveness.

Lead full enterprise sales cycle across the Southeast for Sword Health's AI-driven care platform. Build relationships with HR, benefits, brokers and health plans, deliver executive demos and ROI analyses, manage pipeline and forecasts, differentiate against competitors, and collaborate with clinical and customer success teams to ensure implementation and long-term outcomes.

Lead GTM for Pulse, owning positioning, messaging, competitive intelligence, sales enablement, and market opportunity mapping. Build and manage a solution-specialist team, create buyer-facing materials and ROI frameworks, and use AI-powered market canvassing to surface and pursue enterprise opportunities across segments and geographies.

Drive new employer partnerships with enterprise organizations by managing the full sales cycle, building relationships, and demonstrating value of Sword Health's AI platform.

Lead end-to-end deal execution and governance for enterprise B2B SaaS: manage RFPs and proposals, enforce Salesforce and approval workflows, validate quotes, negotiate commercial terms within policy, drive contract redlines to signature, and build scalable systems and automation to accelerate deal velocity.

Lead GTM strategy for Sword's AI Care offerings to payors (health plans, public sector, unions). Partner with GMs to package solutions, build payor-focused positioning and messaging, produce executive pitch and RFP assets, create sales plays, and run integrated payor campaigns. Enable commercial teams, iterate messaging from market feedback, and drive pipeline, deal velocity, and high-value contracts using AI-augmented marketing methods.