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Director, Sales Operations

Chicago, IL

Hey there. Glad you found us! Flock Freight is a technology company that’s creating a smarter, more sustainable supply chain. Our 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:

As the Director of Sales Operations at Flock Freight, you will play a key and strategic role in establishing new methods and systems to achieve growth across Sales and Customer Success, and play a crucial role in growing Flock’s revenue. Through clear communication of goals, process improvements and implementation, and providing advanced data analytics, you will help to support our Sales and Customer Success teams, while also contributing to the overall business growth strategy. This role reports directly to our COO, and will partner closely with Sales and Customer Success leaders. 

To succeed in this role, you will need to be tech-savvy, data-informed, comfortable both working and supervising in a dynamic and ever-changing environment, and have a strategic mindset to prioritize for success. 

You will be the primary business stakeholder on departmental projects and initiatives, including the execution and continued development of the department's technology stack. You will lead regular staff meetings with sales leadership to help ensure alignment with company goals and objectives.

What You’ll be Doing:

  • Lead sales forecasting, strategic planning, and data processes used within the sales and success organizations.
  • Develop and implement reporting and dashboards to track sales and customer success performance to forecast and target  
  • Design and manage incentive programs to drive desired behaviors across the sales and success organization as the business scales
  • Partner with key stakeholders to identify lead personas and design strategy around the allocation process 
  • Design processes to improve quality and integrity of our sales data, and report on it to make strategic growth decisions
  • Use an analytical eye to identify bottlenecks, drive process excellence, and make overall improvements to sales processes 
  • Manage a lean but efficient team, including a SalesForce Admin, while remaining hands on with the technology and processes 
  • Partner with Marketing leaders to oversee effective tracking of inbound leads through the use of outreach.io and other tools
  • Work collaboratively with the Salesforce Admin and the Business Systems team to lead the evolution of SFDC, while providing key data insights through dashboards and reporting to the leadership team to aid in decision making
  • Proactively monitor and strive to maintain high levels of quality, accuracy, and process consistency in the sales organization's planning efforts


  • Bachelor’s degree in business, management or a similar field preferred
  • 4-6 + years of relevant experience in Sales Operations and at least 2 years in a leadership capacity 
  • Expertise in all things related to data: ability to work with complex data sets. Adept at writing debugging and optimizing SQL queries. Expert in excel/google sheets, and experience with visualization platforms such as Mode, Sigma, Tableau, etc.
  • Advanced knowledge of the Sales and CRM technology landscape, including tools like Salesfoce (SFDC) and Outreach.io
  • Knowledge of statistics and understanding of key business concepts
  • Effective communications skills with demonstrated experience presenting data cross-functionally
  • Experience leading and managing critical projects with cross functional partners and stakeholders, both technical and non technical 

A successful candidate will:

  • Have the desire to join a fast-paced startup with a dynamic and ever-changing environment 
  • Have superb understanding of sales team motivations, customer success, in both an inbound and outbound capacity 
  • Have demonstrated experience in building processes and systems that have measurably improved productivity in Sales and growth for the business
  • Be highly analytical and research oriented: know what data sets are critical to determining success and areas of improvement  
  • Be excited about digging in and being a hands on with the tech stack and processes 
  • Aspire to learn the Freight industry inside and out: Flock is truly changing the way goods are shipped, and we are relentless in pushing for efficiency and reduction of waste.

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.
  • Mental Health: We offer all employees and their dependents (this includes anyone in your household) access to free virtual therapy sessions through HealthiestYou. This free service also offers nutritional help, general medicine and dermatology. 

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!

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We look for Flockers who...

Thrive in a fast-paced, highly collaborative environment
Look to be a part of something bigger than themselves
Enjoy meaningful work and strive to make our world a better place
Come up with clever solutions to difficult problems
Bring a balance of grit and fun to their teams


Unlimited paid time off (PTO)

Flock Freight promotes a healthy work-life balance


Health, dental, vision, and life insurance with HMO, PPO, and premium PPO options


All of our employees receive stock options

Retirement plan

401(k) with sustainable investing options

Flexible spending account (FSA)



Talk to a doctor or therapist wherever, whenever

Commuter benefits

Receive additional commuter funds and pre-taxed dollars to pay for eligible work-related transit

Transportation reimbursement

All employees receive a one-time $150 reimbursement for any non or low-emission mode of transportation

Electric car reimbursement

All employees receive a one-time $500 reimbursement when purchasing an electric vehicle

Paid parental leave

Up to 100% salary for 8 weeks that can be taken intermittently during your child’s first year

Paid pregnancy disability leave

Up to 100% salary for 8 weeks that can be combined with paid parental leave for up to 16 weeks total of leave

Equitable abortion access

100% of travel expenses covered for any employee, spouse, partner or dependent plus one support person, who needs to travel to access care if they live in a state that prohibits such care

Technology reimbursement

All employees receive a non-taxable reimbursement to cover a portion of the cost of your cell phone and internet

Office perks

Cold brew and kombucha on tap, intramural sports teams, surf club, free lunches, and more.

Our philosophy

Our employees are part of the Flock family. We support our family by providing many paths for growth and empowering people to better themselves through professional development, emotional support, and personal health.

Flock Freight takes our commitment to employees a step further by implementing people-focused initiatives that align with our values as a B Corporation. As a B Corp, we have an obligation to uphold the highest standards for several impact areas: sustainability, philanthropy, diversity, and employee wellness.