Top Tech Jobs & Startup Jobs in Chicago, IL

Own the full enterprise SaaS sales cycle, from prospecting and pipeline generation through closing and new business development. Build executive-level relationships within the building construction, design, and real estate industries; qualify complex opportunities using MEDDICC; maintain accurate CRM data and forecasts; achieve sales targets; and collaborate with marketing, customer success, and product teams. The role is based on the US West Coast and requires travel across North America as needed.

The Enterprise Account Executive will drive revenue growth by managing complex sales cycles, closing deals with Fortune 500 companies, and understanding both technical and business needs.

Supports development of Microsoft Power Platform solutions, including Power Apps applications, Power Automate workflows, Power BI dashboards, and SharePoint integrations. Collaborates with stakeholders to automate business processes, manage and validate data, test and deploy solutions, document functionality, and provide customer support. Works with Microsoft 365, Dataverse, Excel, SQL databases, and Agile project teams.

Leads regional sales performance, occupancy growth, and revenue generation across senior living communities. Coaches and develops community sales teams, manages referral partnerships, oversees marketing and lead-generation strategies, analyzes market and performance data, supports budgets and forecasts, and ensures consistent sales processes across multiple locations. Requires extensive regional travel and collaboration with operations and marketing leaders.

Own strategic enterprise customer relationships, driving adoption, retention, renewals, and expansion. Build account plans, run QBRs and executive reviews, identify risks and opportunities, and translate customer data into recommendations. Partner with Talent and Engineering stakeholders, discuss technical workflows and integrations, handle routine product conversations, and relay feedback to Product and Engineering. Help customers apply technical assessment best practices and navigate AI-driven changes in software development and hiring.

Plans, coordinates, and oversees projects from initiation through completion. Develops project plans, manages resources, vendors, scope, schedules, budgets, risks, and documentation, while measuring performance and escalating issues to management. Collaborates with clients, internal teams, and third parties to ensure timely, on-scope, and budget-compliant delivery.

Lead Sidetrade Pay as a global embedded B2B payments business across enterprise, SMB, and mid-market customers. Own product vision, roadmap, monetization, pricing, payment partners, adoption, risk, compliance, revenue, and P&L performance. Build payments and product teams, embed payment experiences into Order-to-Cash workflows, expand into embedded finance, and align Engineering, Sales, Customer Success, Legal, Finance, executives, and external partners across multiple regions.

Lead social-first creative direction across client accounts: own voice and performance-minded creative, translate media signals into messaging, collaborate with creators, execute fast-turn edits and iPhone-native shoots, leverage AI workflows to generate variations, and ensure paid and organic alignment.

Support go-to-market strategy and execution across inbound and outbound channels: define ICPs, join user calls, create Excel demo videos, run outreach using Clay/HeyReach/Instantly, post and measure performance on social platforms, and optimize funnel metrics (visits, conversion, retention, referral).

Consults with automotive retailers to improve customer and employee experiences through coaching, training, facilitation, cultural transformation, and data-driven action planning. Builds relationships with dealership leaders and frontline staff, delivers in-person and virtual sessions, tailors program content, tracks store visits and communications in Salesforce, and supports KPI achievement. Requires extensive travel to dealership locations and independent management of schedules, client engagements, accountability plans, and project deliverables.