Top Tech Jobs & Startup Jobs in Chicago, IL

Leads and scales a team of Mid-Market Account Executives responsible for new-business revenue. Oversees coaching, outbound pipeline generation, deal strategy, forecasting, performance management, hiring, and seller development. Partners with cross-functional teams to improve go-to-market execution, positioning, and sales processes. The role also uses data and AI-enabled workflows to improve sales efficiency and revenue performance in a high-growth SaaS environment.

Support the Data Integrations & Platform team by prioritizing martech integration opportunities, managing partner onboarding and API access, organizing technical documentation, prototyping autonomous AI agents, and defining an integration context layer. Measure process performance and improve agent success rates while collaborating with engineers and AI tooling.

Lead the technical direction of Attentive’s compute and networking platform. Build reusable AWS infrastructure, Kubernetes systems, APIs, and self-service tools while improving reliability, scalability, cost efficiency, security, and developer productivity. Own complex cross-team initiatives from design through production, diagnose sophisticated infrastructure issues, improve CI/CD and observability, mentor engineers, and establish effective AI-assisted development practices.

Leads the technical vision and engineering team for a high-throughput data and event platform. Oversees scalable distributed data systems, pipelines, databases, cloud infrastructure, data governance, and system integration. Partners with AI, ML, analytics, and platform teams to expand self-service capabilities, manages technical debt and architecture decisions, prioritizes projects, and recruits and mentors engineers.

Lead strategy and success planning for strategic SaaS accounts, aligning customer goals, performance, adoption, retention, and growth. Advise clients on lifecycle marketing across SMS, email, and AI-powered channels; coordinate account, services, product, and technical teams; lead business reviews; translate insights into recommendations; manage forecasts, renewals, risks, and expansion opportunities; and build executive-level relationships.

Lead Attentive’s global B2B SaaS Support organization across the US, UK, and Australia. Own the management team, operating model, budget, capacity planning, quality standards, SLOs, partner operations, premium support offering, Support Engineering discipline, and senior escalations. Drive scalable use of AI, automation, offshore capacity, and cross-functional collaboration with Product, Engineering, Customer Success, Services, Sales, and Enablement.

Own the evolution of Attentive’s data platform model and extensibility strategy. Define reusable data objects, relationships, and semantic layers that support diverse customer use cases. Partner with product and engineering to expose data consistently across segmentation, personalization, reporting, APIs, and MCP surfaces. Translate complex infrastructure investments into customer and business outcomes while aligning teams around scalable platform decisions.

Lead corporate security investigations and incident response across identity, endpoints, SaaS, email, and security platforms. Improve detection, response, Zero Trust controls, automation, and incident readiness. Conduct vendor security assessments, support customer security questionnaires, document risk decisions, and collaborate with Security, IT, Engineering, Legal, GRC, Procurement, Sales, and Customer Success teams.

Leads editorial, public relations, strategic communications, executive visibility, thought leadership, media relations, and cross-channel content activation. Develops communications plans for launches and milestones, manages PR agencies and measurement, oversees crisis communications, shapes corporate positioning, and supports employer brand and internal communications. The role partners cross-functionally with product, marketing, analytics, executives, customers, and external media to strengthen brand reputation and engagement.

Act as a technical liaison between customers, Customer Success, and Engineering to triage and resolve technical issues via Zendesk/JIRA/calls. Handle incidents (including on-call), translate customer feedback into engineering actions, develop reusable solutions, identify and escalate bugs, and collaborate cross-functionally to mitigate site event incidents.