Regional Sales Manager Jobs in Chicago, IL
Regional Sales Manager jobs in Chicago are concentrated in the Loop, River North, and the Fulton Market corridor, with strong demand from companies in distribution, technology, financial services, and healthcare. Employers hiring right now include Jobot, Workday, and Rush Enterprises. See the openings below and apply to the ones that match your experience.
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AI doesn't run in one place anymore. It runs in the browser tab, the desktop app, the agent your engineers kicked off, and the copilot embedded in the tools you already pay for. Harmonic Security governs all of it.
Our AI Governance and Control (AIGC) platform sits on the device, inside the interaction, at the moment of action, reading what AI is actually doing (not just the traffic around it) and acting in under 200ms. Security teams get full visibility and control across every AI surface, including the agentic and MCP layer that traditional tools can't see. Their people get to innovate without guardrails slowing them down.
We're gaining serious traction at the intersection of AI and cybersecurity, and backed by investors who know the space: N47, Ten Eleven Ventures, and In-Q-Tel. As AI adoption inside the enterprise accelerates, the ability to safely observe, control, and enforce policy in real time isn't a nice-to-have. It's mission-critical infrastructure. That's what we build.
How We Work: AI-First by Design
Harmonic exists to help enterprises adopt AI safely and at scale. We hold ourselves to that same standard. Everyone here actively uses AI tools to do their best work, from research and writing to building automated workflows. We expect every new hire to bring genuine curiosity for AI and a commitment to working smarter and faster with it.
For some, this means staying open to new tools. For others, it means architecting new systems with AI at the core. We're transparent about expectations for every role, and we give you the tools and support to thrive.
About the Team
Our Sales team is in the early stages of building something extraordinary. We’re a tight-knit, ambitious group laying the groundwork for how Harmonic goes to market. Every rep plays a critical role in building pipeline, landing new logos, and shaping how Harmonic goes to market. We’re builders as much as sellers - refining the playbook, collaborating across teams, and creating repeatable success.
About the Role
We’re looking for a Sales Representative to drive growth across the Chicago/Midwest region. You’ll own the full sales cycle: identifying prospects, building relationships, running demos, negotiating deals, and closing new business. This is an opportunity to join a category-defining company at the ground floor, building your territory while influencing how we sell as a team.
What You'll Do
Own the full sales cycle: prospect, qualify, demo, negotiate, and close
Build and manage pipeline across assigned territory
Develop account strategies in partnership with leadership
Drive outbound prospecting and convert inbound leads
Deliver compelling, tailored presentations and product demos
Collaborate with Marketing, Product, and Customer Success for alignment and feedback
Represent Harmonic at customer meetings and industry events
Contribute to shaping our sales playbook and scaling best practices
What You Bring
4-8+ years of quota-carrying B2B SaaS cybersecurity enterprise sales experience
Experience selling to CIOs and CISOs with an average deal size of $100k+
Track record of hitting or exceeding quota in a closing role
Comfort with outbound prospecting and building a territory from scratch
Strong communication, storytelling, and relationship-building skills
Ability to manage complex sales cycles with technical and business stakeholders
Organized, resourceful, and thrives in a startup environment (startup experience highly desired)
Why Join Us
This isn't just a job, it's a chance to help define a category, and to build this chapter of the story from its first page. We're building at the intersection of AI and security, where the rules haven't been written yet, and the people who join now will write them.
Recognized momentum: named to Rising in Cyber 2026, a signal the market is taking notice
Rare market opportunity: join early in a category-defining company shaping how enterprises tackle one of tech's biggest unsolved problems
Competitive pay and meaningful equity: a real stake in Harmonic's success, not a token gesture
Comprehensive benefits: 401K, generous PTO
A small, high-trust team: transparency, creativity, continuous learning, no politics, no bureaucracy
Thoughtful leadership that cares about your growth, not just your output
Annual global off-sites: past trips include Lisbon and Nashville
Real ownership: you'll shape a new part of the company from day one
Harmonic's Core Values
Flourish in the Unknown
We embrace new, unfamiliar situations that require initiative and rapid decision-making. We orient ourselves quickly and deliver results with minimal guidance.
Never Full
We raise our hands, take on challenges, and assist others whenever possible. We hunger for opportunities to learn and do more.
Perfect Harmony
We support one another to create cohesion and unity. We collaborate openly, share feedback honestly, and help everyone produce their best work.
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Who's Hiring



Top Industries Hiring
- Staffing & Recruiting
- Healthcare & Medical Services
- Retail
- Automotive
- Consumer Goods
Regional Sales Manager Jobs in Chicago: Frequently Asked Questions
How do I get a regional sales manager job in Chicago?
The strongest path is targeting Chicago's dominant hiring sectors: enterprise software, medical devices, commercial real estate services, and industrial distribution. Roles concentrate in the Loop, River North, and along the Fulton Market corridor. Candidates with a proven book of business in the Midwest, existing relationships with Chicago-area buyers, and experience managing teams across a multi-state territory have a clear edge over generalist applicants.
Which companies hire regional sales managers in Chicago?
Companies currently hiring regional sales managers in Chicago include Jobot, Workday, and Rush Enterprises, per current listings on Migrate Mate as of September 2026. Chicago's mix of Fortune 500 headquarters, major healthcare systems, and a dense cluster of B2B software and logistics firms makes it one of the most active markets in the Midwest for this role.
Are there remote regional sales manager jobs in Chicago?
Yes, though regional sales manager roles are less remote-friendly than most, since the work typically involves in-person client meetings and territory travel. About 85% of regional sales manager openings tied to Chicago are remote or hybrid as of September 2026, and those tend to be roles where account management and forecasting are heavier than field selling. Inside sales leadership and SaaS-focused roles represent the largest share of remote-eligible openings in the Chicago market.
How can I get a regional sales manager job in Chicago with little or no experience?
The most realistic entry path is moving up from a senior account executive or territory sales rep role at a Chicago employer, then making the case for a team lead or player-coach position. Mid-size B2B distributors headquartered in the suburbs, along with Chicago's many SaaS and health tech startups, regularly promote strong individual contributors into first-time management roles. Building a track in Midwest territory sales and getting comfortable with pipeline reporting tools gives candidates a concrete advantage when applying locally.
Which industries hire the most regional sales managers in Chicago?
The sectors hiring the most regional sales managers in Chicago are Staffing & Recruiting, Healthcare & Medical Services, and Retail, based on current listings on Migrate Mate as of September 2026. Chicago's role as a Midwest logistics hub, combined with its concentration of healthcare organizations and enterprise technology firms headquartered downtown, keeps demand for sales leadership consistently high across those sectors.
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