Director of Enterprise Sales

Flock Freight

Flock Freight

Sales & Business Development
San Diego, CA, USA · Chicago, IL, USA
Posted on Monday, December 11, 2023

Hey there. Glad you found us! Flock Freight is a technology company that’s creating a smarter, more sustainable supply chain. Recognized on the CNBC “Top 50 Disruptors” list three years running (checking in this year at #20), Flock’s patented technology finds and fills trucks’ empty spaces so shippers can save money, carriers can earn more money, and goods move terminal-free with more accuracy and fewer emissions. Sounds like a pretty big task, right? Welp, it is. But we know we can make it happen.

If you’re looking for the opportunity to make a difference then you’ve come to the right place. We’re looking for folks that are innovative, love collaborating in a fast-paced environment, and find joy and excitement in doing the hard work. If that sounds like you then keep on reading and see if this role is the one for you.

About the Role:

Flock Freight is seeking a Key Enterprise Account Executive to join our team. In this role, you will play a crucial role in acquiring, growing, and retaining enterprise-level customers across the US. Utilizing a consultative sales approach, you will offer our industry-changing products and services, specifically our "FlockDirect" offering, to provide immediate and long-term solutions to customer freight needs. We are looking for a creative and strategic thinker who can build strong relationships, exceed revenue targets, and drive business growth. Please note, this position requires transportation industry experience and though we are an office-first employer, we are open to remote employment for this opening.


  • Independently identify, target, and convert high-quality leads into clients using a consultative sales approach.
  • Cultivate relationships with enterprise-level customers, with a focus on closing major key accounts.
  • Utilize an omnichannel, strategic approach to effectively engage customers within our ideal customer profile.
  • Leverage our CRM (Salesforce) and other internal systems and technology to meticulously document customer information and track deal progress.
  • Build credibility with customers by delivering superior service, tailoring messaging to their needs, and staying informed about market trends.
  • Conduct compelling product demonstrations to prospects and customers.
  • Travel to customer sites and industry events as needed.
  • Utilize in-depth understanding of customer needs, challenges, communication styles, roles, and decision-makers to provide customized solutions.
  • Provide strategic consultation to internal and external stakeholders to ensure successful freight operations.
  • Collaborate across departments at Flock Freight to address customer issues and drive additional business.
  • Mentor and provide guidance to junior sales representatives as required.


  • Minimum of 8 years of experience in a strategic sales role, including some experience within the transportation industry.
  • Demonstrated track record of consistently exceeding revenue and bookings targets.
  • Excellent written and oral communication skills, with the ability to articulate product benefits internally and externally.
  • Strong performance history and a proven ability to meet and surpass sales quotas.
  • Quick learner with the desire to thrive in a fast-paced, technology startup environment.
  • Positive attitude, self-motivation, and adaptability in the face of changing challenges.
  • Goal-oriented mindset with a hunger for success.
  • Exceptional problem-solving skills, with the ability to identify opportunities quickly.
  • LTL/Partial experience is a plus.
  • Bachelor's degree preferred.

Join our team at Flock Freight and become part of our mission to revolutionize the transportation industry. We offer competitive compensation, including uncapped commission potential, as well as a comprehensive benefits package. Apply today and embark on an exciting career journey with us!

The expected on-target earnings range for this position is $160,000 to $260,000 per year. This range reflects typical earning potential in this role, however, our uncapped commission plans allow for top performers to exceed these ranges. When determining an offer, we take into account a variety of factors that are important in making compensation decisions including, but not limited, to: skill sets; experience and tenure; education and certifications; and other business and organizational needs. The disclosed range estimate is based on market data for the greater San Diego area. Salary bands may, in some circumstances, be adjusted to a different geographic area depending on the candidate's position and location. In general, Flock Freight targets the mid-point of this salary range.

In addition to salary, full-time employees are also eligible for an equity package and our competitive benefits that support you and your family as part of your total rewards package at Flock Freight. Our policy is that we target candidates local to one of Flock Freight’s headquarters locations (San Diego or Chicago) and ask that employees work in-office in a hybrid capacity. Ask your recruiter for more specifics about your team's hybrid policy!

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.

Life & Benefits of the Flock:

  • Unlimited PTO: Our Flockers work hard and deserve the time they need to rest and recharge. With no accrual system, we encourage you to the time you need off, when you need it.
  • 401(k) Employer Match: 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! For that reason, we provide a 401(k) plan that offers a 4% employer match.
  • Medical, Dental & Vision: Generous coverage for employees and dependents. Both HMO and PPO options provided with 100% Employer paid options for employees.
  • Hybrid Work Environment: We are happy to offer our employees a hybrid work model to balance both the power of in-person connection and flexibility of work from home. In general, Flock Freight teams are on-site 3 days a week.

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!