B2B Sales Manager – Professional Services SaaS

Hybrid / Semi-Remote, Full Time W2 Role

Offices in Milwaukee, WI and Oak Brook, IL

About Propel Your Business

Propel Your Business (PYB) is a strategic execution platform helping companies track performance, align teams, and increase enterprise value. We combine real-time dashboards, integrated task and meeting management, and proven advisory methodology to empower leaders and their advisors in creating accountability, driving growth, and scaling with confidence.

We’re hiring a B2B Sales Manager to fuel our next stage of growth. This is a direct sales role. You’ll own the process from first outreach to close, driving meaningful conversations and a real impact to the niche we serve.

Why Join PYB?

You’re not just selling software - you’re shaping the future of growing companies. Our platform empowers advisors and executives to align teams, create accountability, and build lasting enterprise value. As part of our sales team, you’ll play a key role in scaling a transformative solution that helps entrepreneurs strengthen their businesses, and, in turn, the businesses they serve.

At PYB, you’ll find{{:}}

• A fast-paced, collaborative team that celebrates initiative.
• The freedom to own your process and innovate.
• A mission-driven product with real impact on business growth.
  
  

This Role is for You If You...

• Have a hunter mentality and love building your own pipeline from scratch.
• Are competitive, driven, and energized by hitting goals.
• Thrive in autonomy but know when to collaborate and ask for input.
• Excel at building relationships and confidently handing them off when value is established.
• Understand the long game (30-90 day sales cycles are typical)
• Treat your CRM like your secret weapon{{:}} accurate, detailed, and up to date
• Balance persistence with professionalism with an aggressive drive and a thoughtful approach.
• Enjoy being part of a small, ambitious team where everyone’s contribution matters.
  
  

What You’ll Be Doing

• Prospecting and booking meetings (with lists and tools provided).
• Sending 50-100 personalized LinkedIn messages weekly.
• Dedicating ~3 hours per day to reaching out; including cold calling from curated lists.
• Driving the full sales cycle - from discovery to consultative close.
• Identifying and qualifying prospective advisors (fractional CEOs, CFOs, COOs, etc.).
• Conducting discovery calls that demonstrate deep understanding of prospect pain points.
• Presenting tailored demos of the software and program.
• Tracking and forecasting all activity in CRM with precision.
• Collaborating in team huddles and attending quarterly prospect events.
• Participating in monthly in-office collaboration and continued learning days.
  
  

You’ll Thrive Here If You Have…

• 3 years of experience in B2B SaaS Sales
• Experience selling to decision-makers (Operations, CEOs, CFOs, CMOs/CSOs)
• Familiarity with entrepreneurship, advisory, finance, or small business growth
• Strong communication, presentation, and relationship-building skills
• Confidence running virtual demos and managing a remote sales process
• A self-starter mindset. You hold yourself accountable and keep yourself organized and on track to hit your goals.
• Live within 90 minutes of Chicago or Milwaukee (or relocating to that area)
  
  

Compensation & Perks

• Base Salary{{:}} $80,000
• OTE{{:}} $150K–$225K/year after ramp-up
• Autonomy in how you hit your goals - this is a results-driven role
• Career growth path into team leadership or enterprise sales
  
  

If you’re a competitive, relationship-driven seller who loves autonomy and thrives on results - let’s talk.

Propel Your Business provides equal employment opportunities to all employees and applicants for employment and prohibits discrimination and harassment of any type without regard to race, color, religion, age, sex, national origin, disability status, genetics, protected veteran status, sexual orientation, gender identity or expression, or any other characteristic protected by federal, state or local laws.

This policy applies to all terms and conditions of employment, including recruiting, hiring, placement, promotion, termination, layoff, recall, transfer, leaves of absence, compensation and training.