Top Tech Jobs & Startup Jobs in Chicago, IL

Lead go-to-market strategy and execution for Outreach platform releases and launches involving governance, security, interoperability, and integrations. Develop positioning, messaging, competitive analysis, enablement, customer content, and partner opportunities. Collaborate with Product, Sales, Marketing, Enablement, Pricing, and Post-Sales teams to drive adoption, retention, growth, and customer value. Apply AI to research, messaging, and launch content while communicating platform capabilities clearly to customers and internal teams.

Lead customer implementations and projects for a SaaS sales engagement platform, including AI-enabled deployments. Conduct CRM discovery, design integrations and configurations, develop testing plans, troubleshoot technical issues, and advise customers on AI adoption and best practices. Serve as a technical subject matter expert for Outreach technologies, collaborate with consultants and customer stakeholders, and support successful platform adoption and measurable business outcomes.

Own global compensation and equity programs, including market pricing, job leveling, salary ranges, merit and bonus cycles, equity grants, and pay equity analysis. Partner with Finance, Recruiting, People Business Partners, and executives on rewards decisions. Maintain compliance with pay regulations, produce reporting from HR and payroll data, communicate rewards programs, and improve global rewards processes using automation and AI.

Owns scalable GTM enablement programs, change management, onboarding, coaching, competitive resources, sales content, and continuous improvement. The role partners with GTM, sales, customer success, product, and marketing leaders to drive adoption and measurable improvements in ramp time, quota attainment, pipeline generation, win rate, and other KPIs. It also uses AI, LMS/CMS platforms, and data insights to improve coaching, content delivery, and program effectiveness.

Manages commercial contract intake, triage, and negotiation within approved templates and playbooks. Partners with attorneys on complex matters, improves contracting processes and documentation, enables business teams, and drives legal technology initiatives. Owns CLM, repository reporting, AI adoption, templates, approval workflows, and multiple concurrent projects while coordinating with Sales, Finance, Revenue Operations, Privacy, and Business Systems.

Own corporate FP&A forecasting, consolidations, cash flow planning, reporting, and financial modeling. Partner with Accounting and cross-functional leaders to analyze variances, improve forecast accuracy, support executive and Board reporting, and guide resource allocation. The role also enhances planning processes, automation, and models covering stock-based compensation, capital expenditures, collections, share count, and long-range planning.

Own the full sales lifecycle for net-new enterprise accounts, from prospecting and discovery through solution demonstrations, negotiation, closing, scoping, and handoff. Build territory and account plans, generate pipeline, forecast accurately, apply MEDDPICC, and sell complex AI-powered SaaS solutions to executive stakeholders. Manage nine- to twelve-month sales cycles and $200,000–$500,000 contracts while partnering with solutions consultants, finance, professional services, and account management.

Own the global partner marketing strategy and annual plan, develop joint campaigns with technology, channel, and SI partners, manage MDF and budgets, coordinate events and webinars, create co-branded content and enablement, adapt programs across North America and EMEA, and measure partner-sourced pipeline, revenue, and ROI.

Lead competitive intelligence and market research across Outreach's AI and revenue platform portfolio. Translate market, customer, and competitor insights into differentiated positioning, battlecards, enablement, and strategic recommendations to influence GTM strategy, product decisions, and executive priorities. Represent Outreach externally and drive cross-functional initiatives that improve win rates and competitive positioning.

Manage a portfolio of enterprise customers to drive adoption of Outreach’s AI-powered features, ensure measurable business outcomes (retention, expansion), lead executive reviews, enable AI adoption and change management, surface data-driven insights and risks, own renewal/expansion strategy, and collaborate cross-functionally with Sales, Product, RevOps, and Professional Services.