New offer - be the first one to apply!
July 15, 2026
Outside Sales B2B Representative - Milwaukee/Madison
Senior • On-site
99,996 - 249,996 USD/yr
Madison, WI
Commission-Based | $100K–$250K+ | W2 Employment | Paid Travel
Join a team helping small and mid-sized businesses maximize profitability. The role is ideal for high-performing sales professionals who thrive in face-to-face B2B sales and want significant earning potential.
Why You'll Love This Role
- Uncapped earning potential – top performers earn $250K+
- Full W2 employment – not 1099
- Comprehensive benefits – health, dental, vision, life insurance, 401(k)
- Paid travel – airfare, hotels, expenses covered
- Tools & support – CRM (Salesforce), leads provided, in-house call center sets appointments
- Professional development – ongoing training
What You'll Do
- Drive face-to-face B2B sales with business owners in your territory
- Manage your pipeline using Salesforce CRM
- Close deals that deliver real impact for clients
- Network at events and leverage exclusive partnership opportunities
- Travel nationally (15–20% overnight)
What We're Looking For
- 10+ years of B2B/direct sales experience
- Proven ability to close high-value deals
- Independent, confident, and results-driven
- Experience owning or managing a business is a plus
- Bilingual skills are a plus (English/Spanish)
Diversity & Inclusion
Equal Opportunity Employer committed to creating an inclusive environment for all employees. All qualified applicants will receive consideration without regard to protected characteristics.
Apply today and join a team where your success is uncapped.
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Waltham, MA
60,000 - 90,000 USD/yr
🏢 Summary: Onsite Sales Development Representative role focused on driving outbound growth, generating new business opportunities, and delivering SaaS product demos to small business owners in the automotive repair industry. The position requires high-volume prospecting, consultative selling, and disciplined CRM pipeline management. Compensation includes base salary plus commission with opportunities for growth and hybrid flexibility after tenure. 🗂️ Requirements: 1+ years outbound sales or business development experience, Proven record of meeting or exceeding sales quotas, Experience with phone-based outreach and high-volume prospecting, Experience conducting product demos and sales presentations, Ability to work onsite 5 days per week in Waltham, MA 📃 Skills: SaaS, CRM, HubSpot, Salesforce, Prospecting, Outbound, Pipeline, Forecasting, Demos 🏢 Description: About the Role We're looking for a Sales Development Representative to help build and scale our outbound motion. This role is focused on uncovering new business opportunities, facilitating product demos, and guiding customers through a streamlined sales process. This is not a passive, inbound role. You will be expected to create opportunities from scratch, navigate organizations, and develop messaging that resonates with small business owners and operators in blue-collar industries. This role is 5x a week onsite in Waltham, MA, with potential for a hybrid schedule after 6 months. Compensation: $90k OTE ($60,000 base salary + commission) You Will - Drive Outbound Growth: Conduct a high volume of calls and outreach to identify and engage decision-makers and economic buyers. - Master the Product: Develop a deep understanding of the SaaS product and its features to effectively communicate value during online product demos. - Consultative Selling: Understand prospects' needs and tailor presentations to their specific pain points. - Pipeline Management: Maintain accurate records of sales activities and customer interactions in the CRM to ensure forecasting accuracy. - Partner for Success: Qualify opportunities and collaborate with the broader sales team on strategy and deal progression. You Have Must Have: - 1+ years of sales experience in outbound prospecting or business development. - Proven track record of meeting or exceeding sales quotas and activity metrics. - Excellent verbal and written communication skills with comfort in phone-based outreach. - Experience performing product demonstrations and consultations. - Ability to commute to the Waltham, MA office. Nice to Have: - Familiarity with the automotive industry, home services, or blue-collar sectors. - Experience selling software or working in a high-growth startup environment. - Experience using CRM tools (like HubSpot or Salesforce) to manage opportunities. Interview Process - Initial Screen (Lead Recruiter) - 30 min - Hiring Manager Interview (Sales Manager) - 45 min - Leadership Interview (CRO) - 30 min - Reference Checks - Completion of the Wonderlic Assessment (20–30 min) We Offer - 100% employer-paid medical insurance - Flexible PTO with a 15-day minimum - Equity package - Generous Parental Leave - 401(k) - Growth & Learning Stipend - WFH Equipment (for home setup) - Collaborative culture with career development opportunities We align our mission of transforming the auto repair experience with opportunities for growth, innovation, and excellence. The hiring process looks beyond credentials and welcomes applicants from diverse backgrounds.