Top Tech Jobs & Startup Jobs in Chicago, IL

Lead legal billing and financial software implementations for law firms. Responsibilities include discovery, billing workflow design, Salesforce and Litify configuration, e-billing, AR and collections, financial reporting, data migration and reconciliation, testing, UAT, training, and go-live support. The role requires collaboration with billing teams, finance staff, developers, and executives while managing project documentation, risks, and status.

Own scoping and proposal creation for professional services, manage Salesforce workflows and reporting, maintain SOW lifecycle and SOPs, support resource planning and handoffs, and partner with RevOps/Finance to ensure forecasting, data integrity, and continuous improvement of services operations.

Supports pre-sales efforts for Litify’s legal billing solution by conducting discovery, understanding law firm billing workflows, configuring and demonstrating time, billing, and accounting functionality, and addressing RFP requirements. The role serves as the billing subject matter expert, enables solution engineers, partners with Product on roadmap feedback, and supports customer-facing sales activities. Requires 3–5 years of law firm billing or related solution engineering experience and monthly domestic travel.

Lead revenue operations strategy, CRM architecture, forecasting, capacity and quota modeling, reporting, AI tooling adoption, and GTM operating cadence. Serve as a strategic advisor to the CRO, drive cross-functional initiatives across Sales, Marketing, and Finance, and build a scalable RevOps team. The role requires hands-on Salesforce administration, AI-to-CRM integration, data modeling, field interventions, and measurable improvements in sales execution.

Own the enterprise SaaS sales cycle from prospecting through close for corporate legal departments. Develop relationships with General Counsel, Legal Operations, and IT stakeholders; conduct consultative presentations; navigate procurement and legal reviews; forecast pipeline in Salesforce; and contribute to go-to-market strategy. Typical deal sizes range from $100K to $1M+ ARR.

Own Litify’s AI Call Intelligence product line end to end, including call capture, transcription, summaries, conversational insights, voice agents, and agentic workflows. Define the roadmap, quality standards, guardrails, and evaluation practices; lead client discovery, beta programs, competitive research, backlog prioritization, and cross-functional delivery. Partner with engineering, design, data science, and go-to-market teams to launch products, drive adoption, and measure outcomes.

Manage full-cycle recruiting across Litify, partnering with hiring managers on requirements, sourcing, screening, interviews, offers, and candidate experience. Coordinate interview logistics, advise on talent markets and recruiting best practices, manage multiple requisitions, and maintain accurate recruiting records in Greenhouse. The contract role supports hiring across technology, sales, marketing, professional services, customer success, and operations.

Lead end-to-end Litify AI implementations for legal clients. Design Salesforce-based AI agent workflows, conduct requirements discovery, configure and deploy solutions, advise clients, define success metrics, and drive adoption. Partner with project managers, sales, engineering, customer success, and product teams while owning technical architecture, documentation, delivery outcomes, and client feedback. The role requires strong Salesforce implementation expertise, AI agent and LLM experience, prompt engineering, and client-facing consulting skills.

Sell Litify's AI-driven legal operating platform to law firms and legal departments. Manage full upsell motions, consult on AI adoption, deliver high-level demos to C-suite, meet sales targets, and articulate ROI of autonomous agents and AI integrations.