Top Tech Jobs & Startup Jobs in Chicago, IL

Own the full sales cycle for Fieldguide’s AI audit platform across public sector organizations, initially focusing on federal accounts. Build territory and go-to-market strategy, navigate complex government procurement processes, exceed revenue targets, develop executive and practitioner relationships, and manage multithreaded enterprise deals. Collaborate cross-functionally to shape messaging, sales processes, and market expansion into state, local, and higher education sectors. The role is fully remote in the United States with up to 30% travel.

Own the end-to-end onboarding program for new sales hires, including strategy, design, delivery, logistics, content, learning paths, certifications, and ramp milestones. Build a scalable, measurable program in a modern LMS or enablement platform, translate sales methodology into practical training, facilitate virtual sessions, assess rep readiness, and continuously improve outcomes using data and stakeholder feedback.

Build and lead enablement programs for Customer Success and Implementation teams, including onboarding, product training, continuous learning, playbooks, and AI-enabled workflows. Identify performance gaps, translate product updates into practical training, improve adoption of tools and processes, and establish feedback loops with Product, Support, Customer Education, and Product Marketing. The role supports stronger renewals, expansions, customer outcomes, and operational efficiency in a growing SaaS organization.

The Mid-Market Account Executive drives full-cycle sales of Fieldguide's AI platform, focusing on prospecting and converting mid-market CPA firms into clients. Responsibilities include exceeding sales targets, building relationships with decision-makers, and collaborating cross-functionally to ensure client satisfaction, all while managing a complex sales process that may involve significant travel.

Lead a full-stack engineering team for core Enterprise product development, balancing management with technical contributions in a remote-first setting.

The Strategic Partnerships Director will activate and scale a partner ecosystem, manage strategic technology partnerships, and drive measurable revenue while collaborating across teams.

Lead end-to-end design for complex, data-rich audit workflows. Partner with Product and Engineering to define strategy, deliver scalable UI, and integrate AI-assisted workflows. Influence design direction, contribute to the design system, mentor peers, and ensure usability, consistency, and regulatory-aware solutions.

Lead end-to-end strategy and execution for conferences, trade shows, sponsorships, and ancillary events. Manage logistics, budgets, vendors, booth experience, speaker submissions, and onsite operations. Align events with sales and marketing priorities, capture and route leads, measure event KPIs and ROI, and travel regularly for onsite execution.

Short-term (8-12 week) contractor role to translate SOX control testing judgment into AI-assisted workflows. Co-develop and prompt AI agents, run and evaluate control tests, document failure modes, design evaluation criteria, and partner with engineering to improve agentic testing.

Manage and scale the accounting function: own monthly close (journals, reconciliations, accruals, reporting), handle revenue, AR, payroll, commissions, expenses, prepaids, and fixed assets. Review contracts, improve workflows (including Rillet), build controls, use AI/automation to streamline close, partner with Strategic Finance and cross-functional teams, and support audits, tax filings, compliance, and new accounting projects.