Director, SaaS Sales ShipperGuide (Chicago)

Chicago / RemoteSales – Digital Sales /Full-Time /RemoteARE YOU INTERESTED IN JOINING AN INNOVATIVE LOGISTICS TECHNOLOGY COMPANY?Loadsmart is a growth-stage technology company valued at over $1 billion (a true Tech Unicorn)!We are a collection of industry veterans and user-centered engineers using innovative technology to fearlessly reinvent the future of freight by helping shippers, brokers, warehouses and carriers to move more with less.With headquarters in Chicago and a globally distributed remote team, Loadsmart continues to attract top talent committed to driving meaningful change. We seek professionals who embody our core values: curiosity, clarity, results, commitment, and teamwork.We are seeking an experienced, results-driven Director of SaaS Sales to lead our ShipperGuide TMS team. This is a player-coach role where you will personally carry and be accountable to an individual sales quota while simultaneously leading, developing, and scaling your team. You own end-to-end sales strategy, execution, and revenue growth for the product; driving alignment, building scalable processes, and consistently exceeding both personal and team targets.A key focus will be maximizing cross-sell opportunities by positioning ShipperGuide’s complementary solutions, increasing customer lifetime value, both through your own book of business and through the deals your team closes. This role will work closely with marketing to ensure timely, persistent, high-quality follow-up on inbound leads, resulting in closed deals through disciplined outreach, consistent cadences, and a consultative, value-selling approach.The ideal candidate is a hands-on SaaS sales leader with experience in multi-product, high-growth environments selling logistics tech/ TMS. You’ll balance strategy and execution, while shifting from competing on features or price to selling business value and ROI.Job Type: (Exempt) - U.S. Only DEPARTMENT: SaaS Sales - Shipperguide LOCATION: Chicago IL or remoteWHAT YOU GET TO DO: Carry and achieve a personal annual sales quota, directly owning a pipeline of net-new and expansion opportunities across ShipperGuideActively prospect, develop, and close strategic deals, modeling best-in-class selling behaviors for the teamOwn and manage a personal book of business, including key accounts and high-value prospects, with full accountability for forecasting and pipeline healthDevelop and execute a unified go-to-market strategy for both ShipperGuide and OpenDock that maximizes market penetration and revenue growthDrive full-funnel sales execution, from lead qualification to closing and onboardingEstablish repeatable sales processes and ensure consistent adoption of tools, CRM hygiene, and reporting standardsPartner with marketing to define and refine ICPs, messaging, and campaign strategiesAlign with Customer Success to ensure a smooth handoff from sales to onboarding and retention initiativesCollaborate with Finance on pricing strategies, discount approvals, and revenue forecastingWork with the Account Management team to proactively identify and execute account growth strategies, including upsells and cross-sellsWork closely with Managed Transportation and Brokerage sales leadership to identify cross-sell and upsell opportunitiesREQUIRED QUALIFICATIONS:7+ years in SaaS TMS sales with at least 5 years in a leadership role, including direct quota-carrying responsibility at the Director level or aboveExperience in public speaking and events Proven track record of personally closing multi-million-dollar deals while simultaneously leading a team to exceed ARR targetsStrong operational discipline with the ability to build scalable, repeatable sales processesProven track record of leading teams to exceed multi-million-dollar ARR targetsExceptional communication, negotiation, and presentation skillsProficiency in Salesforce, SalesLoft, and sales analytics toolsExperience selling into supply chain, logistics, transportation, or similar industriesExperience managing multi-product sales teams or selling a platform with complementary offeringsFamiliarity with both SMB/mid-market and enterprise SaaS sales motionsHistory of working closely with marketing and product to refine GTM strategy$157,000 - $200,000 a yearThe compensation offered for this role will be based on multiple factors such as location, the role’s scope and complexity, the candidate’s experience and expertise. In addition to your base compensation offer, this role is eligible for an incentive bonus andyou will also receive stock options and benefits listed below.WORKING AT LOADSMART:• 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• 401k Match *Applicants must be currently authorized to work in the United States on a full-time basis. Loadsmart will not sponsor applicants for work visas.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.We may use artificial intelligence (AI) tools to support parts of the hiring process, such as reviewing applications, analyzing resumes, or assessing responses and identifying potential inconsistencies or verification signals in application materials based on available information. These tools assist our recruitment team but do not replace human judgment. Final hiring decisions are ultimately made by humans. If you would like more information about how your data is processed, please contact us.