Account Executive

Flock Freight•Chicago, IL

36d•$70,000 - $80,000•Hybrid

About The Position

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. The role involves owning the end-to-end sales process, converting qualified prospects into long-term customers, and driving bookings and revenue growth from both new and existing customers. You will lead discovery conversations to understand customer freight profiles, pain points, and annual freight spend, positioning FlockDirect and Shared Truckload as differentiated, industry-changing solutions. Maintaining a high level of prospect and customer talk time through calls, meetings, demos, and follow-up activities is crucial. Developing and executing account plans to maximize wallet share and long-term revenue potential, building credibility and trust through strong communication, follow-through, and account management, and partnering with internal teams for successful freight execution are key responsibilities. You will also support new customers through onboarding and contract execution, including coordination with legal when required, and accurately track pipeline, account activity, and customer communications within Flock systems, consistently achieving or exceeding monthly gross profit and shipment volume targets.

Requirements

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

Nice To Haves

Bachelor’s degree preferred

Responsibilities

Own the end-to-end sales process, converting qualified prospects into long-term customers.
Generate the majority of their pipeline through self-sourced prospecting.
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.