Director, SaaS Sales ShipperGuide

Loadsmart•Chicago, IL

2d•$157,000 - $200,000•Hybrid

About The Position

Loadsmart is a growth-stage technology company valued at over $1 billion. We are a collection of industry veterans and user-centered engineers using innovative technology to 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.

Requirements

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 above
Experience in public speaking and events
Proven track record of personally closing multi-million-dollar deals while simultaneously leading a team to exceed ARR targets
Strong operational discipline with the ability to build scalable, repeatable sales processes
Proven track record of leading teams to exceed multi-million-dollar ARR targets
Exceptional communication, negotiation, and presentation skills
Proficiency in Salesforce, SalesLoft, and sales analytics tools
Experience selling into supply chain, logistics, transportation, or similar industries
Experience managing multi-product sales teams or selling a platform with complementary offerings
Familiarity with both SMB/mid-market and enterprise SaaS sales motions
History of working closely with marketing and product to refine GTM strategy

Responsibilities

Carry and achieve a personal annual sales quota, directly owning a pipeline of net-new and expansion opportunities across ShipperGuide
Actively prospect, develop, and close strategic deals, modeling best-in-class selling behaviors for the team
Own and manage a personal book of business, including key accounts and high-value prospects, with full accountability for forecasting and pipeline health
Develop and execute a unified go-to-market strategy for both ShipperGuide and OpenDock that maximizes market penetration and revenue growth
Drive full-funnel sales execution, from lead qualification to closing and onboarding
Establish repeatable sales processes and ensure consistent adoption of tools, CRM hygiene, and reporting standards
Partner with marketing to define and refine ICPs, messaging, and campaign strategies
Align with Customer Success to ensure a smooth handoff from sales to onboarding and retention initiatives
Collaborate with Finance on pricing strategies, discount approvals, and revenue forecasting
Work with the Account Management team to proactively identify and execute account growth strategies, including upsells and cross-sells
Work closely with Managed Transportation and Brokerage sales leadership to identify cross-sell and upsell opportunities