Top Tech Jobs & Startup Jobs in Chicago, IL

Leads the East enterprise sales team, driving quota attainment, account-based execution, forecasting discipline, win-rate improvement, and complex deal strategy. Manages, coaches, and performance-manages Account Executives while developing scalable sales processes and enterprise go-to-market motions. Partners cross-functionally with Marketing, Product, RevOps, Enablement, Solutions Engineering, Legal, and Customer Success to improve deal velocity, customer engagement, and segment performance.

Own the full-cycle commercial B2B SaaS sales process, from prospecting and pipeline generation through closing new business. Build territory and account strategies, conduct consultative discovery, deliver tailored software demonstrations, manage qualification and forecasting, and engage executive stakeholders. The role requires quota attainment, self-sourced pipeline generation, strong communication, and experience selling in startup or growth-stage environments. Familiarity with MEDDPICC, MEDDICC, SPICED, or similar sales methodologies is preferred.

Supports a portfolio of commercial B2B SaaS customers by monitoring technical health, resolving bounded integration questions, improving platform adoption, and identifying renewal risks. Creates scalable enablement resources, including academy content, help articles, videos, workshops, and webinars. Partners with Customer Success, Product, and Education teams; documents issues, participates in UAT, supports AI-powered compliance workflows, and escalates complex technical problems.

Own the full-cycle commercial sales process from prospecting through closing, generate and manage pipeline, conduct consultative discovery, present tailored software solutions, and exceed revenue targets. Develop territory and account strategies, engage senior stakeholders, forecast accurately, and collaborate cross-functionally to advance deals. The role requires strong B2B SaaS closing experience, self-sourced pipeline generation, sales methodology expertise, and the ability to sell to security, compliance, risk, or technical buyers.

Own and scale strategic relationships with systems integrators and enterprise audit firms. Drive partner-sourced revenue, co-selling, partner enablement, onboarding, forecasting, and executive engagement. Advocate for Drata products, improve audit experiences, coordinate with Sales, Marketing, Product, Engineering, and Customer Success, and help shape the broader alliance ecosystem strategy.

Leads and develops a commercial account management team serving mid-market B2B SaaS customers. Owns retention, renewals, expansion, adoption, customer health, forecasting, and recurring-revenue outcomes. Builds playbooks, operating rhythms, and cross-functional processes; coaches renewal and expansion strategies; manages escalations and customer risk; and provides leadership with actionable insights. The role also drives CRM discipline, reporting, executive engagement, and scalable customer-success practices.

Define and scale the product operating model to improve planning, prioritization, governance, and execution. Lead company-level roadmap operations, drive portfolio insights, implement tooling and workflows, establish experimentation frameworks, and deliver executive-ready reporting to increase alignment and product impact across cross-functional teams.

The role involves managing full cycle B2B SaaS sales, generating pipeline through various strategies, and delivering tailored presentations to customers while maintaining strong communication and execution discipline.

Lead strategy and execution of global demand generation across digital, integrated, and account-based programs. Build AI-driven multi-channel systems to drive pipeline and revenue, optimize funnel performance, manage budget and reporting, align with Sales/RevOps/Partners, and hire and develop a high-performing demand team.

Lead end-to-end go-to-market planning and execution for major product and feature launches. Drive NPI process improvements, create launch assets and executive communications, enable sales and CS, coordinate cross-functional stakeholders, and standardize launch frameworks to improve speed, quality, and adoption.