Sales Specialist Jobs in Chicago, IL
Sales Specialist jobs in Chicago are concentrated in the Loop, River North, and Fulton Market, with strong demand across B2B technology, financial services, and healthcare across the metro. Employers actively hiring include Google, Meta, and Amazon Web Services. See the openings below and apply to the ones that match your experience.
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Built for Adventure. Trusted Everywhere. Now Hiring.
OtterBox didn’t become the #1 selling case brand in America by playing it safe on the shelf — it earned that spot by protecting the things people can’t live without. Born in Fort Collins, Colorado, and built on a simple promise — “We’ve Got Your Back” — OtterBox stands for toughness, trust, and gear that survives whatever life throws at it.
Now we’re looking for people cut from the same cloth: durable, dependable, and ready for anything. As an OtterBox Sales & Training Specialist, you’ll be the face of the brand on the sales floor — energizing retail teams, wowing customers with hands-on demos (yes, that might mean dropping a phone on purpose), and driving sales at the biggest retailers in the country.
You’ll own a territory of retail stores, building real relationships store by store and becoming the product expert retail teams actually look forward to seeing.
What You'll Do
Sell, Train & Advocate
Bring OtterBox protection to life through live demos and genuine customer conversations that convert browsers into buyers.
Deliver memorable, high-energy training that arms retail associates with the confidence to recommend OtterBox first.
Put product samples in the right hands to spark interest and drive sales conversion.
Build trusted relationships with store associates and managers, turning them into OtterBox advocates long after you leave the store.
Own your numbers — drive sales performance and grow OtterBox market share across your territory.
Keep the Brand Retail-Ready (Light Merchandising)
Refresh OtterBox packaging with updated branding and pricing stickers during store visits — quick, satisfying work that keeps the brand looking as sharp as the products it protects.
Ensure displays, fixtures, and point-of-sale materials are current, stocked, and positioned to sell.
Flag on-shelf availability issues, outdated signage, or display gaps so nothing gets between the customer and the case.
No heavy lifting here — merchandising is a light-touch part of each visit, folded naturally into the selling and training work you’re already doing.
What You Bring
A proven knack for influencing purchase decisions and driving sales results.
Genuine enthusiasm for technology and consumer electronics — you’re the friend people ask before they buy.
3+ years of sales and/or retail experience (wireless retail experience is a big plus).
A polished, engaging presence and the interpersonal skills to connect with anyone — from a first-day associate to a district manager.
The ability to translate rugged engineering into benefits people care about.
Self-motivation and organization to manage a multi-store territory independently.
Full-time access to a vehicle and a valid driver’s license.
Compensation & Perks
Competitive hourly rate, paid weekly — your work shows up in your account every week.
15% performance incentive — hit your goals and add a meaningful bonus on top of your base pay.
Mileage reimbursement at the full IRS rate for travel across your territory.
Why You'll Love It
Represent the #1 case brand in America on a high-visibility national program.
Exclusive product training, demo gear, and samples — you’ll know the lineup inside and out.
Monday–Friday retail schedule with the variety of a new store, new team, and new win every day.
Real ownership: your territory, your relationships, your results.
Join a brand whose whole identity is having people’s backs — including yours.
See All 96 Sales Specialist Jobs in Chicago
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Find Sales Specialist JobsSales Specialist Job Market in Chicago
Who's Hiring



Top Industries Hiring
- Technology & Software14
- Artificial Intelligence5
- Healthcare & Medical Services3
- Consulting & Professional Services3
- Fintech2
Sales Specialist Jobs in Chicago: Frequently Asked Questions
How do I get a sales specialist job in Chicago?
The fastest path in Chicago is targeting the sectors that hire most heavily: enterprise software firms in River North and the Loop, medical device companies along the North Shore, and financial services firms in the West Loop. Candidates who can demonstrate a consultative approach and familiarity with longer B2B sales cycles stand out. Networking through Chicago-area industry events and trade associations adds a real edge in this market.
Which companies hire sales specialists in Chicago?
Employers hiring sales specialists in Chicago right now include Google, Meta, and Amazon Web Services, based on current listings on Migrate Mate as of July 2026. Chicago's hiring mix reflects a broad employer base, from global firms headquartered in the Loop to fast-growing mid-market technology and healthcare companies concentrated in neighborhoods like Fulton Market and River North.
Are there remote sales specialist jobs in Chicago?
Yes, though availability depends on the role: inside sales and software-focused specialist positions are far more likely to be remote or hybrid than field-based or medical device roles. About 59% of sales specialist openings tied to Chicago are remote or hybrid as of July 2026, with most of those concentrated in SaaS and fintech companies. Field-facing and healthcare-adjacent roles in Chicago still run predominantly in-person.
How can I get a sales specialist job in Chicago with little or no experience?
The most realistic entry path in Chicago is starting as a sales development representative or inside sales associate at one of the many SaaS or fintech companies based in River North or Fulton Market, where structured training programs are common. Staffing firms with Chicago operations also place candidates into contract-to-hire sales roles that build a verifiable record quickly. Highlighting any customer-facing retail, hospitality, or account coordination experience from Chicago employers helps bridge the gap.
Which industries hire the most sales specialists in Chicago?
Most sales specialist openings in Chicago sit in Technology & Software, Artificial Intelligence, and Healthcare & Medical Services, per current listings on Migrate Mate as of July 2026. Chicago's role as a hub for enterprise technology, healthcare systems, and financial services means those sectors generate consistent demand, with hiring concentrated among both legacy corporations headquartered downtown and a growing cluster of high-growth companies in the Fulton Market corridor.
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