Top Tech Jobs & Startup Jobs in Chicago, IL

Support the sales team by managing client relationships, meeting with clients online to assess needs, following up on leads, reaching out to prospects, and maintaining client data in a CRM to ensure satisfaction and growth.

Own pricing operations and Deal Desk execution for bespoke enterprise deals. Structure platform, connection, and transaction pricing; enforce discount guardrails; maintain pricing tools, CPQ workflows, documentation, and approval processes. Partner with Sales, Product, Finance, and Legal to operationalize pricing strategy, support negotiations, protect margins, analyze deal trends, and enable field adoption of pricing changes.

The Business Development Representative will generate leads, qualify prospects, and build a pipeline targeting SMB freight forwarders, with a focus on rapid growth in North America.

Create graphic designs, social media assets, animations, web and email visuals, and short-form videos for an open-source software project. Maintain branded asset libraries, align creative work with brand messaging, and potentially help guide the interface design of an SVG animation application. This is a flexible, fully remote, unpaid volunteer opportunity focused on portfolio development and practical experience.

Manage full-cycle bookkeeping for 3–8 clients, including accounts payable and receivable, reconciliations, expense categorization, payroll processing, financial reporting, record maintenance, and tax-season coordination with CPAs. Communicate directly with clients, resolve discrepancies, provide business-performance insights, manage deadlines, and independently solve open-ended problems using QuickBooks Online and related accounting tools.

Owns Lingo.dev’s content production and distribution across technical and nontechnical channels. Responsibilities include writing blogs, research articles, newsletters, changelogs, emails, social posts, ads, SEO content, and demos; interviewing founders, engineers, and customers; distributing content; measuring rankings, citations, backlinks, signups, and return on ad spend; and automating the publishing workflow with Claude and scripting. The role requires strong technical writing, content traction, SEO expertise, AI-assisted production, and independent execution.

Own the CEO’s calendar, follow-ups, project-management systems, hiring operations, content execution tracking, metrics, reporting, and special projects. The role protects executive focus, enforces accountability across teams, coordinates hiring pipelines, analyzes financial and performance data, and builds scalable operating rhythms. It is a high-trust Executive Operations position with a performance-based path toward Chief of Staff responsibilities.

Lead organic social strategy and execution across eight D2C consumer brands. Manage channel strategies, content calendars, audience engagement, UGC sourcing, customer storytelling, performance reporting, optimization, and AI-enabled workflows. Partner with Content, Community, Growth, Customer Experience, and Marketing teams while mentoring social media coordinators and maintaining distinct brand voices across Instagram, Facebook, TikTok, YouTube, and other platforms.

Claims Solutions Partner supporting complex sales cycles through claims-operations expertise, RFP/RFI responses, portfolio analysis, value-case development, and technical onboarding. The role also includes building a global insurance community strategy, organizing events, creating trusted industry content, developing advocacy programs, and measuring pipeline and retention impact.

The Head of Sales will be Modern’s first dedicated seller, responsible for defining and proving its go-to-market motion. This player-coach will generate pipeline, sell across self-serve, mid-market, enterprise, agency, and partner channels, run technical demos, provide pricing and product feedback, and build a repeatable sales playbook. After validating the motion, they will hire and lead a sales team. The role requires strong B2B SaaS sales experience, technical fluency, AI and commerce knowledge, and comfort operating in ambiguity.