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
WHAT YOU GET TO DO:
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
REQUIRED 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 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
Skills Required
- 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
- Proven track record of personally closing multi-million-dollar deals while simultaneously leading a team to exceed ARR targets
- Experience managing multi-product sales teams or selling a platform with complementary offerings
- Experience selling into supply chain, logistics, transportation, or similar industries
- Familiarity with both SMB/mid-market and enterprise SaaS sales motions
- Strong operational discipline with the ability to build scalable, repeatable sales processes, CRM hygiene, and reporting standards
- Proficiency in Salesforce, SalesLoft, and sales analytics tools
- Exceptional communication, negotiation, and presentation skills; experience in public speaking and events
- History of working closely with marketing and product to refine GTM strategy
- Ability to carry and achieve a personal annual sales quota and own pipeline, forecasting, and pipeline health
Loadsmart Compensation & Benefits Highlights
The following summarizes recurring compensation and benefits themes identified from responses generated by popular LLMs to common candidate questions about Loadsmart and has not been reviewed or approved by Loadsmart.
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Leave & Time Off Breadth — Unlimited PTO (“Loadie Time Off”) and sick time are described in postings as available without a limit, broadening flexibility for time away. Availability is noted across many U.S. roles, though exact application can vary by position and location.
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Healthcare Strength — Comprehensive medical, dental, and vision coverage is consistently cited in job postings, indicating a solid core health offering. This breadth forms a standard tech-style benefits baseline for U.S. employees.
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Equity Value & Accessibility — Stock options are frequently offered and positioned as competitive alongside base pay and other benefits. This ownership component is presented as a meaningful part of total rewards.
Loadsmart Insights
What We Do
We are industry veterans and data-scientists using innovative technology to fearlessly reinvent the future of freight. As the ‘nerds of logistics’, we seek intelligence in data to solve deep-rooted inefficiencies in the industry. We give shippers, brokers and carriers access to our data connections (linking supply and demand) and suite of award-winning solutions to strike the perfect balance of cost and service. We’re creating a more efficient and environmentally responsible way to move more with less. For more information, please visit: https://loadsmart.com
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