Sales Executive (Outbound Hunter)

Location: Chicago, IL, USA- Remote/hybrid

Type: Full-Time

About The Company

 A fast-growing logistics technology company on a mission to disrupt the traditional freight brokerage model. We've built a high-performance direct marketplace where shippers and carriers connect in real-time to book and bid on loads. By eliminating unnecessary middlemen, we remove delays, cut costs, and bring radical transparency to the supply chain.

The Role: Are You a Hunter?

We aren't looking for account managers or "relationship builders" who wait for the phone to ring. We are looking for highly motivated, results-oriented Sales Executives with a proven track record of outbound excellence.

This is a pure hunting role. It is designed for the disciplined salesperson who thrives on high activity, measurable achievements, and the thrill of the chase. You will spend your day prospecting, cold calling, and closing shippers onto our platform.

Key Responsibilities

• High-Volume Outbound Prospecting: Build and manage a relentless pipeline of shipper leads through daily cold calls, multi-channel outreach sequences, and persistent follow-ups.
• Product Demonstrations: Deliver compelling demos of our web platform, articulating the clear value of cost savings, transparency, and speed.
• Closing & Onboarding: Convert prospects into active users, guiding them through their first load creation and ensuring long-term platform adoption.
• Pipeline Discipline: Maintain strict CRM hygiene and track KPIs including calls, demos, conversions, and active load volume.
• Feedback Loop: Collaborate with Product and Customer Success teams to share market feedback, helping us refine our outbound playbook and platform features.

What Success Looks Like

We believe in radical transparency. To succeed in this role, you should expect to hit the following benchmarks:

• 150–200 total outbound touches per day.
• 3–5 demos booked per day.
• 10–15 new shippers onboarded per month.

Required Experience & Skills

Must-Have:

• 3+ years of outbound sales experience with documented over-achievement of quotas.
• The "Hunter" Mindset: A proven ability to generate 100% of your pipeline through cold outreach.
• Logistics/Freight Experience: Preference given to those with backgrounds in transportation or supply chain.
• Closing Ability: Strong experience running demos and handling complex objections with confidence.
• Startup Speed: Comfortable moving quickly and adapting in a fast-paced, evolving environment.

Nice-to-Have:

• Experience selling Logistics Tech, TMS, or SaaS marketplaces.
• An existing book of contacts among shippers or freight managers.
• Mastery of CRM and outbound automation tools.

Who This Role is NOT For:

• Those who dislike cold calling or "the grind."
• Those who rely on marketing-generated warm leads.
• Those who prefer a slow, corporate "steady state" over startup urgency.
• Those motivated only by a base salary rather than performance-based wins.

Compensation & Benefits

We reward top performers with a highly competitive base salary commensurate with experience and a performance-driven culture.

Benefits Include:

• Health & Wellness: Comprehensive Medical, Dental, and Vision insurance.
• Financial Security: Company-sponsored Life Insurance, Accident Insurance, and Voluntary Short-Term Disability.
• Retirement: Company-matched 401(k) plan.
• Time Off: Paid Time Off (PTO) and all Paid Federal Holidays.