Information Technology Jobs in Stoughton, WI

Staples is business to business. You’re what binds us together.

Hunts within defined territory to prospect and win net new small to medium business customers. B2Bs are also responsible to ramp and onboard net new won accounts to further expanding our customer base.  It is a high velocity sales position that leverages a prioritized call list to drive prospect engagement remotely by phone, video, face to face, and utilizing digital tools. 

What you’ll be doing:

• Exhibit effective appointment setting skills and set the required number of appointments each week with the correct decision makers.
• Effective Selling Skills
• Utilizing professional selling skills
• Discover prospects incremental and programmatic needs
• Effectively communicates Staples value propositions, capabilities, products and assortments including all categories
• Capable of overcoming objections and closing the sale.
• Utilize prescribed selling tools to prioritize activities and drive efficiency, as well as to document customer engagement and information (ex: Priority List, Tenfold, SFDC).
• Internal Partnerships: Effectively work with customer support/set up teams and category specialists to progress deals forward to closed won
• Implements and ramps wins driving compliance to new account/program
• Expertise of prospect industry buying process’ and ability to support product selection and standardization
• Create sticky accounts which will continue to purchase from Staples
• Integrates feedback from prospects into their sales approach
• New customer assortment and pricing
• Internal Teaming: Individual will need to communicate and work closely with Category Specialists, and Support teams
• Customer Communications: Individual is responsible to communicate with prospects daily in person and face to face in a professional manner

What you bring to the table:

• Strong drive and a desire to win
• Strong aversion to complacency
• Proven ability to view rejection as a learning opportunity and double down on next best actions
• Experience and proven track record of business development
• Strong ability to develop and deliver presentations virtually and in person
• Consultative selling, solutions selling, insight selling, negotiation and advanced client management skills
• Ability to work with product category sales team members
• Strong business, financial, operations and technology acumen
• Ability to analyze business and industry trends to create tailored solutions for prospects based upon Staples value proposition
• Ability to function independently with minimal daily supervision
• Ability and motivation to find, develop, and close sales
• Demonstrated work ethic, self-disciplined
• Ability to succeed in a competitive selling or goal-oriented environment
• Ability to be coached and to incorporate feedback
• Professional appearance and demeanor
• Strong organization and time management skills

What’s needed- Basic Qualifications: 

• 1-3 years of successful sales experience or success as a Staples B2B Sales Associate
• 3+ years experience in PowerPoint, Excel, and Outlook

What’s needed- Preferred Qualifications:

• Knowledge of Customer Relationship Management tool (CRM)
• Industry knowledge, a plus

We Offer:

• Inclusive culture with associate-led Business Resource Groups
• Flexible PTO (22 days) and Holiday Schedule 
• Online and Retail Discounts, Company Match 401(k), Physical and Mental Health Wellness programs, and more! 

Job Description

Ready to jump-start your career and take charge of your earning potential? At Platinum Supplemental Insurance, we're looking for motivated individuals ready to learn, grow, and thrive in a fast-paced environment. Whether you're a recent grad or simply seeking a fresh challenge, this is your chance to earn like a highly educated professional—our proven products and systems are your roadmap to becoming a top earner in sales. If you're prepared to unlock your full potential, let us show you how to build a lucrative and rewarding future.

Why Join Platinum?

Four-Day Workweek

Travel Monday–Thursday to meet with farmers and small business owners, then enjoy your weekends off. Say goodbye to the daily grind and hello to a work-life balance that lets you recharge and spend time on what matters most.

Uncapped Earning Potential

This is a commission-based role, and many of our new reps earn $75,000 or more in their first year, with top performers exceeding $100,000. The sky truly is the limit when it comes to your income.

Ongoing Support & Resources

Focus on building relationships and closing deals while Platinum handles marketing, recruiting, back-office support, and customer service. You'll also benefit from generous bonuses, annual renewal income, and luxury travel incentives for high achievers.

Cutting-Edge AI Training

Get an edge on the competition with our new AI-driven training platform. You'll receive personalized feedback, interactive coaching, and real-time support to help you master Platinum's proven 10-step sales system—faster and more confidently than ever before.

Your Day-to-Day

1. Travel to Your Territory: Meet potential customers (farmers, small business owners, and families) face-to-face to build trust and educate them about Platinum's supplemental insurance solutions.

2. Leverage Our 10-Step Sales Process: Follow a time-tested system that helps you identify prospects, deliver compelling presentations, and close more sales—backed by our powerful AI training.

3. Stay Motivated & Collaborate: Work within a supportive, team-based culture that celebrates wins, shares best practices, and drives everyone to reach new heights.

What You'll Enjoy

• High Earning Potential, No Caps: Earn based on your performance and ambition, without hitting a salary ceiling.
• Residual Income: Benefit from ongoing earnings long after closing a sale, creating a steady income stream.
• Advancement Opportunities: Rise quickly through the ranks and take on leadership roles as you prove your abilities.
• Quarterly Vacations: Earn the chance to recharge on exciting getaways with fellow top performers.
• Company Trips & Events: Enjoy travel and experiences on us—bring a significant other along, all expenses paid.
• Weekends Off: A Monday–Thursday work schedule means you get every weekend free for family time or relaxation.

Who Thrives Here

• Go-Getters: You bring the hunger, discipline, and drive needed to excel in a commission-based environment.
• Clear Communicators: You can connect with people from various backgrounds, build trust, and explain concepts in a simple, relatable way.
• Continuous Learners: You're excited to leverage AI-based training and mentorship to refine your skills and grow quickly.
• Flexible Travelers: You're comfortable with overnight travel Monday–Thursday and are 18+ years old.

Ready to Take the Leap?

If the idea of earning what you're worth, mastering an innovative sales system, and enjoying a 4-day workweek excites you, we'd love to hear from you! Apply today and discover how Platinum can help you unlock a thriving career in sales.

About Platinum

Platinum Supplemental Insurance specializes in helping individuals, families, and businesses secure their financial futures through supplemental coverage. By bridging the gaps left by traditional health plans, Platinum's products offer peace of mind when unexpected health issues arise. With a people-first mentality, robust training programs, and a commitment to growth, Platinum provides the ideal environment for sales professionals to excel—no matter where they're starting from.

Join the Platinum team and see for yourself why so many have launched fulfilling, lucrative sales careers with us.

We're on the hunt for curious, motivated individuals to test and review online money-making opportunities featured on FinanceBuzz. If you enjoy discovering new platforms and sharing your experience, this flexible gig could be perfect for you.

Responsibilities:

• Explore and try various side hustle options (cashback sites, survey apps, etc.)

• Document and report your experience with each platform

• Track potential earnings and ease of use

• Share insights to help improve user recommendations

Requirements:

• Basic tech skills and a stable internet connection

• Comfortable navigating apps and websites

• Ability to work independently

• No prior experience required

Benefits:

• Set your own schedule – work anytime, from anywhere

• Try real ways to earn money online

• Get paid to share honest feedback

• Ideal for side-income seekers, students, or remote workers

Start exploring side hustle opportunities here.

This position is for individuals who want to develop a side income stream while still working full time. You will test different small-scale remote opportunities, learn what works, and grow what produces results.

You’ll use the resources provided to guide you, but your path is self-driven. Over time, you might focus more on the hustles that bring the highest returns.

Responsibilities:

• Review and apply different side-hustle ideas tailored for people with full jobs

• Execute tasks, manage projects or gigs you select

• Keep a simple record of your time vs. earnings

• Iterate and improve your approach as you go

Requirements:

• Stable full-time job or core commitment

• Access to internet and device for remote work

• Willingness to test ideas and adapt

• Organization, follow-through, and consistency

Bonus Skills:

• Ability to analyze which hustles are viable

• Comfort with trial and error

• Some prior side-gig experience (but not required)

Benefits:

• Fully remote

• Flexible hours

• Potential to grow side income steadily

• No micromanagement

We’re offering a role for someone who wants to lead their own side-income project in their spare time. You’ll explore various proven side hustles, select the ones that fit your lifestyle, and run them like mini projects.

You’ll get curated content to guide your decisions. The goal is to find manageable, sustainable income streams that don’t interfere with your full-time role.

Responsibilities:

• Evaluate side-hustle options and pick those you believe you can execute

• Plan and carry out your selected projects or tasks

• Track metrics—time invested, return, conversion rates

• Refine your focus toward the best-performing hustles

Requirements:

• Employed full time or committed to another primary role

• Basic skills for remote work (internet, device)

• Project mindset: set goals, measure outcomes, adjust

• Persistence and consistency

Strong Traits:

• Analytical

• Willing to adapt

• Growth-oriented

Benefits:

• No fixed schedule

• Remote and flexible

• Ability to scale your side work over time

• Tools and guidance included