Responsibilities
- 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
- You’ll balance strategy and execution, while shifting from competing on features or price to selling business value and ROI
- 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
Benefits
- Parental leave: The primary caregiver is able to take three months of fully paid leave and one additionally month of working half days for a total of four months of leave
- Company Equity: Ever wanted to have a stake in a company? Upon hire, Loadsmart employees are granted options that vest over a four‑year period
- Team Building Events: Enjoy local company sponsored events to meet and network with fellow Loadies: from hackathons to local meetups, we love collaborating while having fun
- Healthcare: We offer competitive medical, dental, and vision coverage for you and your family
- Claim Advocacy with MMA: Expert advocacy and guidance on benefits and claims
- HSA/FSA: You can use pre‑tax dollars to pay for healthcare costs for you and your dependents
- DCFSA: We offer DCFSA to help parents reduce their total taxable income when paying for childcare
- LPFSA: On eligible plans, LPFSA helps pay for vision and dental expenses that are not fully covered by your insurance
- Life and AD&D Insurance: Loadsmart provides both Life and Accidental Death and Dismemberment insurance at no cost to you with the options to increase coverage at your own expense
- Short Term/Long Term Disability Insurance: Loadsmart provides short and long‑term disability coverage at no cost to you
- Flexible PTO? Holiday: Enjoy paid time off without a limit, with manager approval and national holidays of your location
- 401K wwith Match: We support our employees’ retirement goals by offering a per pay period match to our Traditional and Roth 401K plans
- 401K with Match: We support our employees’ retirement goals by offering a per pay period match to our Traditional and Roth 401K plans
The ideal candidate is a hands‑on SaaS sales leader with experience in multi‑product, high‑growth environments selling logistics tech/ TMS. Proficiency in Salesforce, SalesLoft, and sales analytics tools. Exceptional communication, negotiation, and presentation skills. Familiarity with both SMB/mid‑market and enterprise SaaS sales motions. Proven track record of personally closing multi‑million‑dollar deals while simultaneously leading a team to exceed ARR targets. Experience in public speaking and events. Strong operational discipline with the ability to build scalable, repeatable sales processes. History of working closely with marketing and product to refine GTM strategy. Experience managing multi‑product sales teams or selling a platform with complementary offerings. Experience selling into supply chain, logistics, transportation, or similar industries. 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 leading teams to exceed multi‑million‑dollar ARR targets.
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