Sr. Director, Enterprise Sales (Logistics / Brokerage)

Chicago / Remote

Full Time Senior-level / Expert from USD 250K
Loadsmart, Inc. logo
Loadsmart, Inc.
Loadsmart is a logistics technology platform that enables shippers, carriers, and brokers to efficiently manage an automated supply chain. Backed by data scientists, engineers, and world-class support — Loadsmart integrates seamlessly to give...
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→ Do you have experience leading a team of Enterprise Sales Executives?→ Are you interested in disrupting the logistics industry by leveraging technology? → Do you want to join a rocketship that has had +200% growth of year-over-year revenue?
If so, nice to meet you! We are Loadsmart and we are adding a new Sr. Director, Enterprise Sales to lead our newly hired Sales Executives as we continue to fuel our growth by accelerating the acquisition of new customers. These sales executives are targeting large enterprise shippers, communicating our value proposition and closing the business.
This position will manage a small team and require strong collaboration skills to work with the Account Management team and the SDR team as well as to partner closely with our marketing, partner sales, solution sales and product teams. You will create a culture of sales success and lead by example.
REPORTING TO: Tim Evans, VP, Enterprise SalesLOCATION: Anywhere in the US with regular travel as the world opens back up to meet prospects and clients


  • Oversee a team of Enterprise Sales Executives and Account Executives focused on acquiring new large enterprise shippers through execution of complex entire sales cycle, from customer meeting to closing consultative partnership, you have control and build the relationships
  • Establish and proactively manage individual sales quotas, call targets and other key performance metrics 
  • Partnering with Marketing to aggressively drive high level of sales outreach primarily focused on acquiring and onboarding new customers while 
  • Partnering with the Customer Success team to retain and grow existing customers
  • Manage the effective use of Sales collaboration Tools (SalesForce and SalesLoft)


  • 4+ years direct B2B sales leadership experience managing a team at a brokerage or logistics firm selling to Enterprise accounts, with a track record of consistently exceeding sales quotas personally
  • Proven aptitude for managing pipelines, forecasting, territory planning and sales KPIs.
  • Strong understanding sales methodologies and influencing skills; ability to negotiate and build strong business relationships internally and externally.
  • A comprehensive understanding of the function of TMSs and/or integrations
  • Experience with Salesforce is strongly preferred; using a CRM is paramount to this role


  • A self-starter, innovative, result-focused and team-oriented
  • Someone who helps add value to customers in a strategic way
  • Possessing a strong ability to establish and manage relationships with prospects
  • Embracing a growth mindset, sense of curiosity and strong problem solving skills; you are constantly learning about emerging market trends to identify potential opportunities and gaps
  • Tech-savvy including ability to leverage (learn, if necessary) collaboration tools including Google Suite and Slack as well as navigate core HR Systems (Bamboo, Lever)
Rewarding Top Performers• Competitive base salaries (including a non-recoverable draw during your 6 months of ramping)• Aggressive uncapped commission program with accelerators after quota - paid on both net revenue and integrating a new customer on our platform• $250k “Fast Start” bonus for each whale you land in your first two years (we’ll talk through details with you!)• Extremely competitive Equity package
Good Health• Comprehensive Medical, Dental, and Vision insurance plans• 401k Match up to $5,000 regardless of salary• Short and Long Term Disability Insurance covered 100% by the company• Teledoc (remote doctors) and Talkspace (mental health counseling) membership fees covered 100% by the company
Happiness!• 10 Paid holidays, plus 15 days of accrued PTO for a total of 25 paid days off per year• An opportunity to work with an inclusive, global community of Loadies across 15 countries united by our core value of Teamwork • Regular recognition, feedback, and transparency across all levels; we offer monthly Business Updates, monthly “Ask Me Anything” Sessions with the CEO and Quarterly Equity updates• Opportunities for you to join our community service initiatives and donation drives• Lots of employee engagement activities both offsite and onsite; if you’re in Chicago expect to have an amazing time as we move into our beautiful new 35,000 sq foot office where we host happy hours, free lunches, free breakfast, lots of games (ping pong, pool, arcade, etc) plus get out of the office regularly for company social events (i.e. bowling, baseball games, golf outings)Are you up to the challenge? 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.
Job region(s): North America
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