March 25, 2024
USA Only
From $120K USD

President of Freight Brokerage

About the job:



Loadsmart is a growth-stage start-up technology company valued at over $1 billion (a true Tech Unicorn)!

We have recently created a new President of Freight Brokerage position to lead both supply and demand side of our Loadsmart brokerage business. This role requires a demonstrated track record of success leading entire brokerage P&Ls with direct experience on both the shipper and carrier side for sales and operations.  The ideal candidate must have significant scale-up experience as a builder and clear examples of doing this at scale.

This individual will be someone who has consistently overachieved in high-growth environments and has actively contributed to building high-performance, customer-centric organizations. It will be critical that this individual has been a part of scaling a rapidly growing business by driving adoption within a solution-oriented team. The role will require an individual to establish results and performance-based culture while leveraging their leadership team to build out the organization and vision for the shipper/carrier sales and operations teams.

DEPARTMENT: Digital Brokerage

LOCATION: This position can be remote anywhere in the US (or in offices in Chicago); the expectation is this role will generally work during Central business hours as Chicago is HQ. If not based in Chicago, regular travel to HQ, as well as key Customer sites, would be expected.


  • Strategy and Leadership
  • Sales - Alignment and Execution
  • Operations - Customer Growth and Adoption

Strategy and Leadership

  • Lead both shipper and carrier teams consisting of enterprise, mid market and SMB along with carrier operations, pricing strategy, capacity development, carrier sales and specialized services
  • Build and drive a strategy for the supply side(carrier) and the shipper side(brokerage) that leverages an integrated approach and delivers a sustainable service experience
  • Identify and prioritize target markets and prospects for current and new products, according to growth opportunities
  • Monitoring industry trends to identify new opportunities for growth or ways to improve existing products or services in both the shipper and carrier areas
  • Establishing pricing structures, terms of payment and other contractual obligations with clients
  • Work directly with CTO and CPO to create new products and solutions for shippers, such as drop and hook, trailer leasing, etc. Focus areas and roadmaps, bringing customer needs and revenue opportunities together to drive higher revenue per customer.
  • Demonstrate unrelenting commitment to achieving the plan numbers, and establish the required positive tension and energy with the team

Sales - Alignment and Execution

  • Attract and retain a team of stellar performers
  • Operationalize leading edge execution across the teams and achieve world class performance from lead generation to sales conversion, applying advanced methodologies and tools, automation and programmatic execution where applicable
  • Create and drive specific programs such as account plans to increase adoption and share of wallet on existing clients, whilst acquiring new clients
  • Create and drive specific programs to increase customer satisfaction and retention, across all products and services
  • Align the different teams’ structures, performance standards, metrics and commission programs to best in class practices
  • Systematically staff against highest return market opportunities, explicitly planning capacity and allocation against ROI goals
  • Provide solid forecasting and the ability to explain results on a period by period basis through detailed variance analysis

Operations - Customer Growth and Adoption

  • Prioritize service delivery as #1 KPI for growth and retention
  • Review and develop plan to formally tier and manage our carrier customers to ensure engagement and delivery on shipper side and carrier satisfaction and growth on carrier side
  • Formalize a carrier tiering program with reward/penalty and allows us to better control outcomes with shippers
  • Leverage and scale teams to improve operational excellence in pricing, RFP strategy, account planning, account management, forecasting and reporting processes
  • Manage key customer relationships, driving success and satisfaction, and creating additional commercial opportunities
  • Lead customer-centric, customer journey and value proposition initiatives by partnering with Product, Marketing and Operations
  • Clearly define and track against a quantitative definition of success, which includes operational metrics such as churn, customer satisfaction and NPS
  • Manage key customer relationships and participate in closing strategic opportunities; Increasing and maintaining customer happiness with their offerings and, in their ability to address their needs, elevating their chances to recommend their offerings to others


  • At least 15 years in organizations in a GM-type role at a freight brokerage leading teams both selling and delivering multiple products to both enterprise and SMB customers (ideally a blend of software and services), with 5+ years in a senior leadership position leading cross-functional teams over 50 people
  • Extensive experience leading a fast-paced brokerage and freight, operations, account management or customer experience organizations, with demonstrated results in driving enhanced productivity and improved operational metrics (ideally leveraging OKRs)
  • Proven track record on partnering with product and engineering teams to launch new successful products and services in a fast-paced, iterative and hypothesis-driven framework
  • Proven ability to systematically and rapidly diagnose the opportunities and challenges facing a business, set strategy, decide on a course of action, then enroll & mobilize the organization to deliver successful outcomes
  • Conceiving, developing and executing commercial and/or customer journey strategies for a multi-product company selling across SMB and Enterprise
  • Driving change, growth strategy implementation, strategic planning, complex financial analysis, analytical and valuation skills with strong critical-thinking and sound business judgment, including the ability to develop a strategic perspective for target identification and evaluation
  • Demonstrated track record of recruiting and fielding an "A" team  Experience while building new capabilities where one has not previously existed is desirable
  • P&L experience is a must, as would experience with software-based products and services

* Due to position requirements, this position cannot be performed in New York City or the states of Colorado, Washington, or California.


• Competitive base salaries - we believe in rewarding top talent 

• Extremely competitive Equity package - become a shareholder in our company!

• Loadie Time Off - PTO and sick days without a limit

• Comprehensive Medical, Dental, and Vision insurance plans (US applied)

• 401k Match

Apply today! 

At Loadsmart, we believe our biggest asset is our people. We are proud to be an equal opportunity employer, hiring and developing individuals from diverse backgrounds and experiences to add to our collaborative culture. Loadsmart treats all candidates and employees with respect and does not discriminate in our recruiting, hiring, and promoting processes, including on the basis of race, color, religion, sex, age, sexual orientation, gender identity and/or expression, national origin, veteran status, or disability.

It is the policy of Loadsmart that all offers of employment made shall be contingent upon successful completion of electronic background check(s). These checks will be job-related, consistent with business necessity and conducted by our vendor, pursuant to all applicable laws, rules, policies and procedures of our candidates' specific locale.

USA Only
From $120K USD/Year

Company Benefits

Share this job:
👉 Please let Loadsmart know you found this opening on Remote Army, with your support we can keep providing you with fresh quality remote jobs.

Don't miss out on new remote jobs!

Get curated job alerts daily on your preferred categories and access all features!

Join Telegram Channel