Top Tech Jobs & Startup Jobs in Chicago, IL

Own Help Scout’s growth and monetization strategy across signup, onboarding, trial-to-paid conversion, customer expansion, pricing, and packaging. Lead experimentation across new business and expansion, build growth infrastructure and playbooks, partner cross-functionally, and manage a growing team of product managers. The role requires hands-on experimentation, outcome-based pricing expertise, technical fluency, AI understanding, strong writing, and prior B2B SaaS growth leadership.

Own outbound pipeline generation and full-cycle sales for mid-market B2B SaaS customers. Responsibilities include prospecting, account targeting, product demonstrations, business-case development, negotiations, closing deals, building the upmarket sales playbook, collaborating with Product, Marketing, and RevOps, and managing pipeline coverage, forecasting, and sales targets.

Lead Help Scout’s product design team as a player-coach, managing experienced designers while maintaining high craft standards. Own design principles, the design system, AI experience strategy, design workflows, and capacity allocation. Partner with Product, Engineering, Brand Design, and executive leadership to shape product direction, improve cross-functional delivery, and ensure cohesive customer experiences across a fully remote organization.

Lead and own Help Scout's paid and performance marketing strategy to grow signups and revenue. Manage channel mix, creative, bidding, and budget allocation; evaluate new channel investments; partner with Sales/RevOps to tie paid spend to pipeline; align paid and organic acquisition; own AI-driven discovery presence; run rapid experiments; and build a 12–18 month roadmap for scaling the function.

Lead product marketing strategy and positioning for a B2B SaaS/AI platform. Build and scale the product marketing function, enable sales and support, drive competitive intelligence, own major product launches, and represent the product externally through content and thought leadership. Coach and grow at least one direct report.

Lead the Conversations product group (Inbox and Copilot) end-to-end: set vision and roadmap, own monetization, ship AI-powered workspace features, partner across Autonomy, GTM, and CS, spend time with customers, and hire and coach PMs while driving revenue and product craft.

Build customer-facing intelligence features end-to-end with a frontend focus using TypeScript and React. Ship production-grade LLM capabilities (RAG, embeddings, prompt engineering), ensure reliability, observability, accessibility, and stay close to customers to measure outcomes.