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$70k–$80k/yr
Full-time
bachelor degree
401(k), Medical insurance, Dental insurance, Vision insurance, Equity package
Posted 7d ago
~40 hrs/week
Responsibilities
The Account Executive is responsible for managing the end-to-end sales process, focusing on self-sourced outbound prospecting to generate a robust pipeline. They will lead discovery conversations, position freight solutions, and maintain strong customer relationships to drive revenue growth.
Requirements
Candidates should have at least one year of direct, customer-facing outbound sales experience and a strong understanding of freight or logistics. A bachelor's degree is preferred, along with proven ability to meet sales quotas and a self-motivated, competitive mindset.
Full job description
Core Responsibilities
Own the end-to-end sales process, converting qualified prospects into long-term customers.
This is a highly outbound, prospecting-driven role. Account Executives are expected to generate the majority of their pipeline through self-sourced prospecting. Success requires comfort with autonomy, ambiguity, and creating opportunities from scratch.
Drive bookings and revenue growth from both new and existing customers.
Lead discovery conversations to understand customer freight profiles, pain points, and annual freight spend.
Position FlockDirect and Shared Truckload as differentiated, industry-changing solutions tailored to each customer’s needs.
Maintain a high level of prospect and customer talk time through calls, meetings, demos, and follow-up activities.
Develop and execute account plans to maximize wallet share and long-term revenue potential.
Build credibility and trust through strong communication, follow-through, and account management.
Partner with internal teams to ensure successful freight execution, including managing accessorials, overrides, and approvals.
Support new customers through onboarding and contract execution, including coordination with legal when required.
Accurately track pipeline, account activity, and customer communications within Flock systems.
Consistently achieve or exceed monthly gross profit and shipment volume targets.
What Success Looks Like
A consistently full pipeline driven by high outbound activity and smart prospecting.
Strong close rates and sustained revenue growth across a book of business.
Customers who clearly understand and see value in Flock’s differentiated freight model.
Reliable achievement of activity, shipment, and gross profit goals.
Long-term customer relationships built on trust, performance, and strategic partnership.
Qualifications
Bachelor’s degree preferred
1+ year of direct, customer-facing sales experience in an outbound or mixed outbound environment, with responsibility for prospecting, discovery, and closing
Strong understanding of LTL freight; experience with Partial or network-based solutions is a plus
Proven ability to consistently meet or exceed sales and activity quotas
Competitive, self-motivated, and driven by performance, achievement, and earning potential.
Enjoys the hunt of outbound selling and takes pride in creating opportunities rather than waiting for them
Comfortable with cold calling and proactive outbound selling
Strong communication, negotiation, and problem-solving skills
Ability to quickly learn and confidently sell new, technology-driven products
Motivation driven by results and ownership of outcomes
Desire to work in a fast-paced, high-growth environment
Compensation
The base salary range for this position is $70,000 - $80,000 per year + commission opportunity with meaningful upside. This reflects typical earning potential in this role based on market data and individual factors including skill sets, experience, and geographic location. In addition to salary, full-time employees are eligible for an equity package and competitive benefits that support you and your family as part of your total rewards package at Flock Freight.
Life & Benefits of the Flock
Hybrid Work Model: As an organization we value in-office collaboration, working cross-functionally, and winning together. Through scheduled in-office and work from home days, we are able to work more efficiently and collaboratively.
401(k): We know Flock may just be a stepping stone in your epic journey, but we want to be sure you’re setting your future self up for success!
Medical, Dental & Vision: Generous coverage for employees and dependents. Both HMO and PPO options provided.
Our promise to you
Flock Freight is committed to creating an environment that’s fair and inclusive. We fill our open positions based on qualifications, merit, and business needs. We value the skills of people from all backgrounds and are proud to hire, promote, and retain talent from a diverse candidate pool. Diverse perspectives are central to innovation at Flock Freight and make our team better. We're interested in your inherent abilities, not just the skills you bring from your last role - if you think you have what it takes to succeed in the role but don't check every box, please still get in touch. We'd love to start a conversation with you.
Flock Freight has zero tolerance for behavior that negatively impacts marginalized groups, including women, people of color, veterans, immigrants, people with disabilities, and members of the LGBTQIA+ community. We invite people of all identities to join the Flock!
We are targeting talent in the San Diego AND Chicagoland Area.
Related keywords
SalesAccount ExecutiveOutboundProspectingFreightLTLShared TruckloadPipelineCold callingRevenue growthLogisticsAccount managementNegotiationCustomer-facingTechnology-drivenHybrid work
Shared Truckload: Enjoy the advantages of truckload shipping while only paying for the space you need
Industry
Transportation, Logistics, Supply Chain and Storage
Company size
201-500 employees
Founded
2015
Headquarters
Encinitas, California
LinkedIn followers
36,754
Total funding
$459M
Flock Freight is the largest Shared Truckload (STL) freight brokerage in the U.S., transforming underutilized truckload capacity into tangible value: cost savings for shippers, increased earnings for carriers, and a smaller carbon footprint. Their AI-powered, patented pooling technology optimizes across Flock’s entire customer network, combining shipments from thousands of businesses into efficient Shared Truckloads. With STL, shippers enjoy truckload-level service while only paying for the space they need. Trusted by thousands of customers, from some of the largest enterprises to growing brands, Flock Freight delivers an unmatched combination of cost efficiency, exceptional service, and a streamlined shipping experience.
Offices: 701 S Coast Hwy 101, Encinitas, California 92024, US · 318 N Carpenter St, Chicago, Illinois 60607, US
Freight ServiceLogisticsSoftwareTransportationShippingShipping & TruckingTransportation and logistics
How many Transportation jobs are open in Chicago, IL right now?
There are currently 1,375 open transportation positions in Chicago, IL listed on Clera. New openings are added daily as companies post roles.
Which companies are hiring for Transportation roles in Chicago, IL?
Companies currently hiring include United Airlines, Worldwide Flight Services (WFS), AutoZone, Chicago Transit Authority, RXO, Inc., among others. Browse the listings above to see every active employer.
Are there remote or hybrid Transportation jobs in Chicago, IL?
Yes — 217 of the 1375 open transportation positions offer remote or hybrid work (51 remote, 166 hybrid).
How do I apply for Transportation jobs in Chicago, IL?
Each listing links directly to the employer's application page. Apply early — fresh listings get the most recruiter attention in the first two weeks.