Top Tech Jobs & Startup Jobs in Chicago, IL

Conduct high-volume outbound prospecting within existing customer accounts to identify new buyers, departments, and expansion opportunities. Make 500+ daily power-dialer calls, research accounts, map decision-makers, communicate product value, conduct discovery, handle objections, schedule qualified demos, maintain accurate activity records, and meet pipeline and meeting goals. The role includes sales training, coaching, and development in AI-powered sales technology.

Leads and transforms an inbound SDR organization supporting product-led growth. Owns pipeline generation, SDR hiring and coaching, lead scoring, routing, automation, reporting, attribution, GTM workflows, and conversion to MRR. Partners with Revenue Operations, Sales, Product, Marketing, and Lifecycle teams to optimize sales engagement, improve efficiency, implement AI-driven processes, and guide organizational change.

Own customer retention, renewals, cancellation-save opportunities, and account expansion for SMB customers. Conduct consultative sales conversations, product demonstrations, negotiations, and closing activities while identifying churn risks and increasing product adoption. Manage high-volume customer interactions, maintain accurate Salesforce records, and collaborate with Customer Success, Sales, Support, and Product teams to improve customer outcomes and recurring revenue.

Conduct outbound prospecting through cold calls and emails, qualify leads, demonstrate product value, address objections, maintain account records, and collaborate with Account Executives to advance qualified opportunities. The role requires learning SaaS product capabilities, researching prospects and personas, building relationships, and contributing to business development goals in a fully remote environment.

Corporate Counsel will lead commercial SaaS contracting, global privacy and data compliance, product and AI counseling, employment matters, corporate governance, and legal operations. The role negotiates customer, vendor, technology, and data agreements; manages GDPR and CCPA/CPRA compliance; advises Product, Engineering, Security, IT, Sales, Finance, and People teams; develops legal templates and playbooks; and coordinates outside counsel while scaling legal processes.

Owns the full partner sales cycle for Seamless.AI integrations, including prospecting, relationship building, negotiation, deal structuring, and launching native, OEM, white-label, workflow, and marketplace integrations. The role partners with product and engineering teams to ship integrations, manages partner-sourced revenue, and drives both pipeline growth and successful deployments.

Identify, qualify, and follow up with inbound sales leads through phone, email, LinkedIn, video, and chat. Maintain product expertise, deliver a strong prospect experience, document lead interactions in the CRM, and coordinate qualified handoffs to Account Executives. Collaborate with Marketing, Sales, and Operations to improve lead quality and deal flow while providing additional sales support as needed.