Mid Market Account Executive, (Brokerages)

Augment; Chicago (IL); On-site; USD 95,000 - 150,000; Full time

Benefits offered by this job

Competitive salary + stock options

Health, Vision, Dental benefits

Flexible PTO

Monthly stipend

Job summary

Augment is seeking a Mid-Market Account Executive to own a book of business within the brokerage segment. You will run complex, multi-stakeholder deals, build pipeline from outbound, and close with rigor.

Demos will be delivered alongside a Solutions Engineer for technical evaluations and ROI justification for Augie. You will target mid-size freight brokerages and 3PLs, map buying committees, and travel up to 50% for meetings and strategic deals.

Qualifications

• 3–5 years of full-cycle B2B SaaS sales with mid-market deals.
• Experience mapping buying committees and driving multi-threaded deals.
• Strong discovery and ROI-focused selling mindset.
• Self-sourced pipeline is the default approach.
• Highly organized and process-driven to move complex deals.
• Entrepreneurial mindset; able to define the playbook.
• Comfortable in ambiguous, early-stage environments.

Responsibilities

• Own a defined mid-market territory or named accounts within the brokerage segment.
• Run consultative, multi-threaded deals (60–120 days) from outbound through close.
• Conduct discovery calls with VPs of Operations, Directors of Brokerage Ops, Controllers, and IT leaders to build ROI for Augie.
• Deliver product demos, often with a Solutions Engineer for complex evaluations.
• Map and manage buying committees; keep multiple stakeholders aligned.
• Build and maintain full pipeline via self-sourced outbound using LinkedIn Navigator, Seamless.ai, and 6sense signals.
• Keep HubSpot clean and your forecast accurate.
• Travel up to 50% for customer meetings, events, and deals.
• Share field intel to sharpen messaging, ICP, and product roadmap.

Skills

Full-cycle B2B SaaS sales

Multi-stakeholder deals

Discovery and ROI selling

Self-sourced pipeline

Organization & process

Playbook development

Comfort with ambiguity

Deal momentum management

Tools

HubSpot

LinkedIn Sales Navigator

Seamless.ai

6sense

Clay

Job description

About Us

Supply chains are broken. Let's fix it.

We are a team of engineers, product designers, and customer champions building Augie, Augment's AI teammate for supply chain. Augie reasons and acts like a seasoned operator automating the busywork of quoting, dispatch, tracking, billing, and collections - for freight brokers, 3PLs, for-hire carriers, private fleets, and distributors.

Our team has scaled billion-dollar companies, built delightful products, and powered billions in commerce. Now, we're solving supply chain's toughest challenges with AI.

If you thrive in fast-paced, high-impact environments and want to define how AI reshapes supply chain.

Overview

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 LinkedIn Sales Navigator, Seamless.ai, and 6sense intent signals

• Keep HubSpot 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 HubSpot, LinkedIn 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.