Top Tech Jobs & Startup Jobs in Chicago, IL

Own full-cycle enterprise sales for strategic accounts across TX/OK/LA/AR. Prospect, qualify, manage POCs and trials, negotiate multifaceted pricing, build C-level relationships, and close $100k–$500k deals while traveling monthly to meet customers.

In this role, you will engage with mid-market customers, driving sales through cold calling and building relationships to close deals ranging from $20k to $100k.

The Account Executive for Mid Market is responsible for driving sales by engaging mid-sized customers, managing trials, and closing deals ranging from $20k to $100k, while traveling approximately 25% of the time.

As an Account Executive, you will drive sales to mid-market customers, handling POCs, negotiations, and building relationships to enhance operations through IoT data.

Leads Samsara’s GTM AI Engineering team, building production AI agents, copilots, workflow automations, predictive models, and evaluation systems. Owns the shared AI platform, architecture, governance, observability, model routing, cost controls, and CRM intelligence. Partners with Sales, Customer Success, Support, Product, and Engineering to drive adoption and measurable business impact. This hands-on director role involves coding and prototyping approximately 70% of the time while hiring, developing, and guiding the engineering team.

Execute Samsara’s internal communications strategy across newsletters, employee meetings, change communications, organizational announcements, video, and other channels. Partner cross-functionally with leadership, People, Legal, and go-to-market teams; gather employee feedback to improve communication channels; and reinforce company culture. The role requires strategic communications experience, strong storytelling and presentation skills, creative content development, and comfort working in a fast-paced, changing technology environment.

Manage enterprise customer implementations of Samsara’s IoT platform, including deployment planning, adoption roadmaps, training, progress tracking, and account health monitoring. Build trusted relationships with executives and end users, explain technical solutions, resolve challenges, and coordinate with Sales, Support, Sales Engineering, and Product. Mentor Customer Success and Support teams while helping customers achieve safety, efficiency, and sustainability outcomes.

Develop and communicate ROI and business value strategies for prospective and existing enterprise customers. Conduct quantitative analysis, ROI modeling, and trial management to demonstrate Samsara product value. Consult on implementation, change management, and customer experience; present recommendations to executives; and lead cross-functional initiatives that improve operational excellence, engagement quality, and organizational adoption of value-based selling.

Owns enterprise sales cycles from prospecting through close, develops executive relationships, manages complex $100,000+ deals, conducts solution-based selling, and consistently exceeds quota. The role involves strategic outbound prospecting, multi-stakeholder engagements, pricing negotiations, customer trials, and monthly customer travel. Candidates should have strong enterprise sales experience, C-level relationship skills, and familiarity with operations, finance, or IT stakeholders.

Own enterprise sales cycles for Samsara’s Connected Operations Cloud, from strategic prospecting and qualification through close. Build executive relationships, manage complex $100,000–$500,000 transactions, conduct solution-based sales campaigns, coordinate proofs of concept and trials, negotiate pricing, and engage stakeholders across operations, finance, and IT. The role is remote in the U.S., requires EST or CST hours, and involves monthly customer travel.