Top Tech Jobs & Startup Jobs in Chicago, IL

Leads Redwood’s enterprise organic search program across multiple websites, covering technical SEO, content optimization, GEO, and AEO. Owns strategy, roadmaps, audits, keyword research, performance measurement, executive reporting, and conversion optimization. Partners with web, UX, content, product marketing, and demand generation teams to increase visibility, demos, pipeline, and revenue. Evaluates SEO tools, monitors search trends, mentors practitioners, and drives strategic initiatives across traditional and AI-powered search platforms.

Serve as the primary technical and strategic partner for existing customers. Drive adoption, conduct health checks and business reviews, identify expansion opportunities, deliver demonstrations and proofs of concept, troubleshoot escalations, coordinate cross-functional teams, manage concurrent projects, and advocate for customer needs. The role combines technical solutioning, account growth, post-sales adoption, and customer success leadership.

Build and maintain integrated financial models, forecasts, budgets, and scenario analyses for revenue, costs, cash flow, and SaaS metrics. Analyze performance variances, customer economics, cloud costs, and gross margins. Partner with Finance, Sales, Revenue Operations, Product, and infrastructure leaders to validate assumptions, improve forecasting, and support strategic decisions. Present concise financial insights and recommendations to executives and non-financial stakeholders.

Design, develop, and maintain a native IBM i connectivity agent for Redwood RunMyJobs. Responsibilities include job submission and monitoring, spool and queue handling, CL/RPG invocation, security integration, API connectivity, troubleshooting, performance and reliability improvements, architecture, code reviews, testing, documentation, and collaboration with product and engineering teams. The role also requires validating AI-assisted solutions against authoritative IBM i documentation.

Leads Redwood’s strategic SAP and AWS alliances across partnership strategy, joint go-to-market, pipeline growth, deal execution, executive relationships, product roadmaps, partner KPIs, compliance, and ecosystem development. Collaborates with sales, marketing, Professional Services, Product Management, Engineering, and operations to expand joint business opportunities and represent Redwood at partner events and industry forums.

Partners with Sales leadership to improve business processes, workflows, territory planning, forecasting, and operational performance. Maintains Salesforce data integrity and hygiene, administers Clari, owns QBR execution, analyzes pipeline and churn trends, and develops reporting and dashboards. The role provides actionable insights, drives cross-functional collaboration, and supports scalable, data-driven sales operations.

Drive revenue growth across strategic B2B software accounts through new business development, upselling, cross-selling, solution selling, account planning, and executive relationship management. Develop customer-centric opportunities, manage sales pipelines, create proposals, negotiate deals, coordinate internal service teams, and address client risks and conflicts.

Lead FP&A activities for R&D and Support functions: manage budgets and forecasts, build financial models, perform variance analysis, monitor Opex and AWS spend, prepare reports for leadership, and partner cross-functionally to drive cost efficiency and financial decision-making.