Top Tech Jobs & Startup Jobs in Chicago, IL

Technical leader responsible for architecting, building, and scaling the developer portal and PaaS. Drive architectural direction, write and review code, mentor engineering teams, collaborate with SRE and stakeholders, evaluate new technologies, troubleshoot complex issues, and improve engineering processes and platform reliability.

Lead forecasting and reporting for revenue, ARR, and bookings; build models and KPIs; run variance and ad-hoc analyses; write SQL against Snowflake; partner with sales ops and systems teams; support annual planning; improve FP&A processes and mentor juniors.

Provides strategic consulting to K12 institutions using Instructure products, including Canvas, Mastery Connect, and Impact. Develops change-management, communication, training, and engagement plans; delivers product training and coaching; analyzes usage challenges; creates adoption resources, model courses, help documents, and presentations; and supports platform implementation, instructional best practices, and organizational adoption. Builds relationships with education stakeholders, monitors progress after consulting sessions, identifies additional support needs, and travels to client sites as required.

Manage strategic higher education accounts by developing success plans, leading executive business reviews, monitoring customer health, driving product adoption, and supporting retention and expansion. Use data and generative AI to identify risks, improve workflows, and strengthen customer engagement. Collaborate with Product Management, Sales, Renewal Representatives, and leadership while maintaining CRM records and managing a substantial SaaS portfolio.

Drive new business and expand market share for Parchment K-12 by prospecting K-12 districts, managing full sales cycle, delivering demos, negotiating contracts, collaborating cross-functionally, forecasting in CRM, and representing the product at events.

Lead a two-person pod to find, validate, build, and sell AI-enabled products. Own product specs, prototype quickly, secure pilot customers, prove revenue, and manage P&L and stage-gates until scale or fold.

Lead GTM finance for planning, forecasting, P&L ownership, headcount/resource planning, commission analysis, and financial reporting. Mentor a senior analyst, build repeatable processes, support strategic initiatives with financial modeling, and identify AI-driven automation opportunities across GTM Finance.

Serve as the primary Sales Operations partner for a North American business unit. Coordinate forecasting, pipeline reviews, performance reporting, planning, territory segmentation, quota modeling, and business reviews. Analyze sales metrics, identify risks and opportunities, improve data quality, and deliver leadership recommendations. Partner cross-functionally with Finance, Marketing, Customer Success, and technical teams to define requirements, automate reporting, streamline workflows, and lead analytical projects.

Sells Canvas to new enterprise clients across Texas, guiding prospects through evaluations and purchasing decisions. Responsibilities include developing sales strategies, building executive relationships, forecasting performance, meeting quotas, preparing tailored proposals, expanding pipelines through referrals, and maintaining accurate Salesforce CRM records. Requires 5+ years of sales experience, preferably in enterprise software or SaaS, consultative selling expertise, executive-level engagement, and willingness to travel up to 50%.

Own Cash EBITDA and Free Cash Flow models, coordinate annual planning and forecasting, analyze financial performance and variances, reconcile reporting with Accounting, and prepare insights for leadership. The role partners across Finance and business teams to connect profitability, working capital, and cash generation while improving and automating FP&A processes.