Top Tech Jobs & Startup Jobs in Chicago, IL

Own Shepherd’s end-to-end brand and content strategy across LinkedIn, email, website, partnerships, and communities. Develop messaging, thought leadership, founder-led content, case studies, guides, and campaigns; manage content distribution and repurposing; and align content with growth, pipeline, and revenue goals. Analyze performance, capture customer insights, test new channels, and build scalable content systems in an early-stage AI and legal services company.

Lead the architecture, development, and operation of cloud infrastructure for an AI-native legal platform. Own CI/CD, developer tooling, Kubernetes and containerized workloads, AI infrastructure, observability, security, compliance, reliability, scalability, and cost optimization. Partner with engineering and product teams, establish infrastructure standards, and hire and mentor future infrastructure engineers while ensuring sensitive legal data is handled securely.

Advise startups and growth companies on corporate matters, including entity formation, governance, compliance, venture financings, IP strategy, and commercial agreements. Draft and negotiate legal documents, support multi-jurisdictional compliance, and help build AI-enhanced legal workflows, firm processes, culture, and client service standards. Contribute to thought leadership and business development while working closely with the founding attorney.

Own the full B2B sales cycle for an AI-native legal services and software company, from lead generation through closing. Conduct discovery with founders and operators, deliver demos and proposals, manage pipeline, and meet revenue targets. Partner with the founding, marketing, and growth teams to refine positioning, pricing, messaging, CRM workflows, and sales processes. Build relationships within the startup ecosystem and help establish a scalable sales organization.

Chief of Staff partnering with the CEO and founding team to drive company priorities, cross-functional initiatives, operating rhythms, fundraising support, metrics analysis, process improvement, hiring, and execution. The role operates across product, go-to-market, operations, and strategy in a remote, early-stage AI-native legal services company.

Generate qualified pipeline through outbound and inbound outreach, research startup prospects, personalize messaging, qualify leads, schedule meetings, manage CRM data, and build scalable sales development systems. The role collaborates with founders, marketing, and growth teams to test messaging, improve conversion rates, provide market feedback, and shape the company’s go-to-market strategy.

Build and lead Shepherd’s go-to-market and growth engine from the ground up. Own positioning, messaging, acquisition, partnerships, content, community, outbound, CRM, marketing automation, onboarding systems, and growth analytics. Develop relationships with venture funds, accelerators, and founder communities to generate pipeline. Personally close deals while creating scalable sales playbooks, channels, and experiments in collaboration with the founding team.

The Founding Paralegal will support attorneys on corporate, employment, contracting, fundraising, compliance, and governance matters. Responsibilities include drafting and managing legal documents, coordinating workflows, conducting legal research, maintaining client records, communicating with clients, and developing playbooks, templates, and technology-enabled processes to scale legal service delivery.

Design, build, and scale Shepherd’s core platform, backend systems, APIs, user-facing applications, and AI-powered legal workflows. Architect secure, reliable infrastructure for sensitive legal data, collaborate with legal and product teams, build internal tools, optimize performance, and own technical decisions. The role also involves rapid prototyping, mentoring and recruiting engineers, and contributing to SOC 2 readiness and data privacy practices.

Advise startups and growth companies on corporate law, entity formation, governance, compliance, venture financings, intellectual property strategy, and commercial agreements. Negotiate funding instruments and contracts, support multijurisdictional compliance, and help develop AI-enhanced legal workflows. As an early team member, contribute to firm strategy, processes, culture, client service, thought leadership, and business development.