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Mid Market Account Executive; Brokerages

Job in Chicago, Cook County, Illinois, 60601, USA
Listing for: Augment
Full Time position
Listed on 2026-08-31
Job specializations:
  • Sales
    Business Development, B2B Sales
Job Description & How to Apply Below
Position: Mid Market Account Executive, (Brokerages)

Mid-Market Account Executive

We're looking for a consultative, process-driven Mid-Market Account Executive to own a book of business within the brokerage segment. You'll run complex, multi-stakeholder deals, build pipeline from the ground up, and close with rigor and precision. This role is for someone who has graduated from high-velocity selling and wants to go deeper — longer cycles, bigger deals, and more sophisticated buyers.

You'll target mid-size freight brokerages and 3PLs companies with real buying processes, multiple decision-makers, and meaningful budgets for technology that changes how they operate.

What You'll Do
  • Own a defined mid-market territory or named account list within the brokerage segment
  • Run consultative, multi-threaded deals (typically 60–120 days) from outbound through close
  • Conduct discovery calls with VPs of Operations, Directors of Brokerage Ops, Controllers, and IT leaders to build a quantified ROI case for Augie
  • Deliver compelling product demos, often alongside a Solutions Engineer for complex technical evaluations
  • Map and manage buying committees keep multiple stakeholders aligned and moving
  • Build and maintain a full pipeline through self-sourced outbound using Linked In Sales Navigator, Seamless.ai, and 6sense intent signals
  • Keep Hub Spot clean and your forecast accurate
  • Travel up to 50% of the time for customer meetings, industry events, team offsites, and strategic deals
  • Share field intel to sharpen our messaging, ICP, and product roadmap
What We're Looking For
  • 3–5 years of full-cycle B2B SaaS sales experience with mid-market deal complexity
  • You've run multi-stakeholder deals; you know how to map a buying committee and keep momentum across multiple contacts
  • Strong discovery and business acumen; you sell outcomes and ROI, not features
  • Self-sourced pipeline is your default; you don't wait for inbound to show up
  • Organized and process-driven; you keep complex deals moving without dropping threads
  • Builder mentality energized by defining the playbook, not frustrated by its absence
  • Comfortable with ambiguity and early-stage environments
Bonus Points For
  • Experience selling into freight brokerages, 3PLs, or logistics technology companies
  • Background at companies like Echo Global Logistics, Coyote, MoLo, Transplace, or similar
  • Familiarity with Hub Spot, Linked In Sales Navigator, Seamless.ai, or Clay
  • Prior experience in a founding or early AE role at a startup
Why Join Us?
  • Competitive Salary + Stock Options
  • Comprehensive Health, Vision, and Dental Benefits
  • Flexible PTO
  • Monthly stipend
About Augment

At Augment, we set out to create a fully autonomous AI platform — Augie — that streamlines operations and reclaims the human element in supply chain. Our founders recognized a pattern: talented professionals were stuck handling manual data entry, phone calls, and repetitive tasks, instead of focusing on high-impact problem-solving and strategic decision-making.

That insight became our mission — to free supply chain professionals from busywork so they can focus on what truly drives business growth. Augment isn't just about efficiency; it's about transforming an entire industry by empowering teams with AI-driven solutions that make supply chain smarter, faster, and more adaptive.

Join Us On This Journey!

Augment is an Equal Opportunity Employer and values diversity at our company. We consider all qualified applicants without regard to race, color, religion, national origin, gender, gender identity or expression, sexual orientation, age, marital status, veteran status, disability, or any other legally protected status.

Augment complies with federal, state, and local laws regarding equal employment opportunity and reasonable accommodation. If you need assistance or an accommodation during the application or interview process, please contact your recruiter.

We also consider qualified applicants with arrest and conviction records in accordance with applicable federal, state and local fair-chance / ban-the-box laws (for example, but not limited to, the California Fair Chance Act).

Our hiring process uses AI-powered tools to assist with screening and evaluating applications based on job-related criteria. All AI-assisted outputs are reviewed by human recruiters who make all decisions about which candidates advance in the process.

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