Sales Jobs in Madison, WI
Sales jobs in Madison, Wisconsin are concentrated in the research park corridor near the University of Wisconsin campus, the downtown Capitol Square district, and the East Washington Avenue tech and startup corridor, with strong demand in software, healthcare, and financial services. Employers hiring right now include Macy's, Target, and Storm Guard. Scan the live roles below and apply to whichever ones fit.
Find Sales JobsOverview
Showing 5 of 222+ Sales jobs











Outside Technology Sales – Build an A.I.-Proof Career with Unlimited Income
Are you self-motivated, competitive, and driven to build a career where your income reflects your hustle?
Want a profession that won’t be replaced by A.I. as customers will always need a hands on, trusted sales advisor who can build relationships, solve problems, and close deals?
Are you tired of selling a product once, getting paid once, and watching someone else collect the recurring revenue?
What if you could build a book of business that pays you year after year?
If that sounds like the career you want, keep reading.
We are hiring two ambitious Outside Technology Sales Representatives to sell the future of business technology to organizations throughout Southern Wisconsin. You’ll help companies leverage cybersecurity, cloud solutions, managed IT services, infrastructure upgrades, and A.I.-enabled technologies to become more secure and productive.
This is not a dead-end sales job. This is a long-term, high-income career where you build recurring residual commissions that compound over time. Imagine waking up on January 1st with commissions already earned before making your first call of the year.
Why This Opportunity Stands Out:
- Sell cutting-edge technology including cybersecurity, managed IT, cloud, and A.I.-driven solutions
- Build residual monthly commissions that continue long after the initial sale
- Paid professional sales and technology training
- Unlimited earning potential
- Work directly with customer IT, Office Managers, Owners and Executives
- Develop a highly valuable, future-proof career skill set
What You’ll Do:
- Complete our paid onboarding and sales training program
- Prospect new business through cold calling, email, networking, and referrals
- Build and manage your own sales territory
- Work company
- Meet with business decision-makers
- Create quotes, proposals, and technology recommendations
- Close new contracts and projects
- Maintain strong customer relationships that generate recurring commission income
What We’re Looking For:
- 1–5 years of successful sales experience is preferred but no required
- Highly competitive, self-motivated, organized, self-managed and goal-oriented
- Strong communication and relationship-building skills
- Comfortable learning about technology and explaining it to business leaders
- Organized, detail-oriented, and persistent
- Proven track record of finding and closing deals
Compensation and Benefits:
- Competitive base salary
- Uncapped commission
- Residual recurring commissions
- Long-term annuity-style income
- Paid training and professional development
- 401K with company matching
- Health and Dental Insurance with Vision Discount Program
- Hybrid Work-from-home opportunities
- Competitive PTO accruals
Top performers can build substantial six-figure incomes as their recurring commission base grows each year!
About Us:
DirectNetworks is an entrepreneurial IT company founded in 1999 that provides Cloud and Managed IT Services to customers regionally. DirectNetworks has built its business model and reputation around above-and-beyond customer support. As an organization, we are proud to be large enough to support the careers of our staff in advanced IT technologies and sales, but remain small enough to be a happy and professional, yet non-corporate environment.
Launch Your Career
If you want a high-energy career where your effort directly determines your income, and you’re excited about selling technology that businesses rely on every day, we want to hear from you.
Apply today and start building an A.I.-proof sales career with unlimited earning potential.
Equal Opportunity Employer.
Job Type: Full-time
Pay: $50,000.00 - $110,000.00 per year
Benefits:
- 401(k)
- 401(k) matching
- Cell phone reimbursement
- Dental insurance
- Health insurance
- Mileage reimbursement
- Paid time off
- Paid training
- Work from home
Work Location: Hybrid remote in Madison, WI 53713
See All 222+ Sales Jobs in Madison
Find roles in Madison that match your experience and apply in just a few clicks.
Find Sales JobsSales Job Market in Madison
Who's Hiring



Top Industries Hiring
- Distribution & Wholesale
- Automotive
- Telecommunications
- Biotechnology & Pharmaceuticals
- Retail
Sales Jobs in Madison: Frequently Asked Questions
How do I get a sales job in Madison?
The strongest entry points in Madison are software and SaaS companies in the University Research Park, healthcare technology firms along the East Washington corridor, and financial services companies downtown near the Capitol. Candidates with experience in consultative or solution-based selling stand out in Madison's market, which skews toward longer enterprise sales cycles. Networking through local groups like the Greater Madison Chamber of Commerce also opens doors quickly.
Which companies hire saless in Madison?
Employers hiring saless in Madison right now include Macy's, Target, and Storm Guard, based on current listings on Migrate Mate as of July 2026. Madison's hiring base is a mix of established insurance and financial firms, fast-growing health tech companies, and venture-backed software startups, many of which cluster near the university and the East Washington innovation corridor.
Are there remote sales jobs in Madison?
Yes, though remote availability in sales depends heavily on role type, with inside sales and account management positions being far more remote-friendly than field or territory roles. About 43% of sales openings tied to Madison are remote or hybrid as of July 2026, reflecting strong demand from Madison's tech and SaaS employers. Inside sales and business development roles with Madison-based software companies are the most consistently remote.
How can I get a sales job in Madison with little or no experience?
The most realistic entry path in Madison is a sales development representative role at one of the city's many SaaS or health tech companies, which routinely hire candidates without formal sales backgrounds and provide structured training. Local employers in insurance, staffing, and media also hire entry-level account coordinators and inside sales associates. A demonstrable comfort with outreach, strong written communication, and familiarity with CRM tools like Salesforce give candidates a clear edge in Madison's competitive entry-level market.
Which industries hire the most saless in Madison?
The sectors hiring the most saless in Madison are Distribution & Wholesale, Automotive, and Telecommunications, based on current listings on Migrate Mate as of July 2026. Madison's position as a university city and state capital means that software, government-adjacent services, and healthcare technology generate particularly consistent sales hiring throughout the year.
Related Jobs in Wisconsin
See All 222+ Sales Jobs in Madison
Find roles in Madison that match your experience and apply in just a few clicks.
Find Sales Jobs