Top Tech Jobs & Startup Jobs in Chicago, IL

Provides strategic and operational legal guidance to executives and the board; drafts and negotiates SaaS, commercial, vendor, privacy, and partnership agreements; supports sales, finance, procurement, HR, cybersecurity, M&A, financing, intellectual property, insurance, and compliance matters; manages outside counsel and builds scalable legal processes, systems, and workflows.

Acquire and grow mid-market customers for AI-powered customer experience, contact center, unified communications, and business communication solutions. Generate pipeline through prospecting, referrals, networking, partners, and inbound opportunities; manage complex multi-stakeholder sales cycles; conduct consultative discovery; develop account plans; present solutions; maintain CRM data and forecasts; use AI-enabled sales tools and analytics; and collaborate with marketing, partners, solution consultants, customer success, and product teams.

Own the full B2B sales cycle from prospecting and qualification through negotiation, closing, account expansion, renewals, and post-sale relationship management. Build trusted customer partnerships, conduct site visits, represent the company at industry events, and collaborate with leadership, product, and design teams to incorporate customer feedback. The role is remote, focused on U.S. time zones, and requires significant domestic and international travel.

Manage a high-volume sales pipeline, present accounting and tax services through Google Meet, educate small business clients, build relationships, follow up throughout the sales cycle, and maintain accurate CRM records. The role requires consultative selling, strong communication, disciplined time management, technology adaptability, and achievement of sales targets in a fully remote environment.

Own the full enterprise sales cycle as Voidhawk’s first sales hire, from prospecting and discovery through technical evaluation, negotiation, procurement, and close. Build pipeline independently, establish repeatable sales processes, refine ICP and messaging, maintain CRM discipline, forecast accurately, and provide market feedback to product teams. The role requires selling complex security or technical infrastructure solutions to security, engineering, executive, finance, legal, and procurement stakeholders, while using AI to improve research, outreach, preparation, follow-up, proposals, and CRM workflows.

Own enterprise customer engagements from discovery through implementation, adoption, and go-live. Design BigPanda solutions, integrations, workflows, data models, and automations; write scripts and tooling; troubleshoot complex implementation challenges; advise technical stakeholders; create reusable architecture patterns; and mentor Solutions Architects. The role requires strong experience with observability, ITSM, incident response, enterprise implementations, coding, architecture, documentation, and consultative communication.

Own onboarding and offboarding, optimize Rippling and related HR systems, administer benefits and employment changes across US, Portugal, and Canada, and manage compliance, immigration, and work authorization processes. Support performance reviews, leveling, recognition, and other people programs while building scalable, AI-enabled workflows and documentation. Partner across teams and help expand manager support and HRBP capabilities as the company grows.

Manages and expands strategic B2B accounts by increasing revenue, developing account plans, building customer relationships, coordinating internal resources, leading solution development, and achieving sales, profitability, and customer satisfaction objectives. The role requires complex multi-location account experience, strategic planning, negotiation, CRM proficiency, and frequent overnight travel.

Designs and leads secure, scalable full-stack and enterprise architecture solutions for federal modernization initiatives. Responsibilities include application and cloud architecture, API and systems integration, microservices, data flows, technical design reviews, modernization strategy, security and compliance alignment, and mentoring engineering teams. Requires strong Java and frontend expertise, cloud experience, and the ability to translate mission and business requirements into durable technical solutions.

Manages strategic client accounts, builds consultative relationships, drives retention and expansion sales, identifies opportunities, prepares proposals and reports, supports onboarding and service delivery, and serves as an escalation point. Maintains CRM records, tracks KPIs, collaborates across departments, and supports revenue goals through account management and business-to-business selling.