Director, SaaS Sales ShipperGuide

Loadsmart; Chicago (IL); On-site; USD 157,000 - 200,000; Full time

Benefits offered by this job

Unlimited PTO

Comprehensive insurance

401(k) match

Equity packages

Job summary

Loadsmart is seeking a Sales Director to lead and develop a sales team while managing personal quotas. The role involves defining sales strategies, ensuring processes are repeatable, and collaborating with various departments to drive revenue growth.

Ideal candidates have extensive SaaS TMS sales experience, exceptional communication skills, and a history of successfully closing multi-million dollar deals. The position offers a competitive salary and incentive bonuses.

Qualifications

• 7+ years in SaaS TMS sales, with at least 5 years in leadership.
• Experience in public speaking and events.
• Proven track record in closing significant deals.

Responsibilities

• Carry and achieve a personal annual sales quota.
• Prospect, develop, and close strategic deals.
• Align sales with marketing for campaign strategies.

Skills

SaaS TMS sales experience

Leadership in sales

Communication skills

Negotiation skills

Salesforce proficiency

Multi-million dollar deal closing

Tools

SalesLoft

Sales analytics tools

Job description

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 assisting shippers, brokers, warehouses and carriers to move more with less.

We seek professionals who embody our core values: curiosity, clarity, results, commitment, and teamwork. This role is a player‑coach position: you will personally carry a sales quota while leading, developing, and scaling a team. You own end‑to‑end sales strategy, execution, and revenue growth for the product; drive alignment, build scalable processes, and consistently exceed both personal and team targets.

What you get to do

• Carry and achieve a personal annual sales quota, 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 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 leading a team to exceed ARR targets
• Strong operational discipline with the ability to build scalable, repeatable sales processes
• 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

$157,000 – $200,000 a year
In addition to the base salary, this role is eligible for an incentive bonus and stock options.

Working at Loadsmart

• Competitive base salaries
• Extremely competitive equity package
• Unlimited PTO and sick days
• Comprehensive medical, dental, and vision insurance
• 401(k) match
• Applicants must be authorized to work in the United States on a full‑time basis; Loadsmart does not sponsor 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. We treat all candidates and employees with respect and do not discriminate based on race, color, religion, sex, age, sexual orientation, gender identity, national origin, veteran status, or disability.

All offers of employment are contingent upon successful completion of electronic background checks. These checks will be job‑related, consistent with business necessity, and conducted in accordance with all applicable laws and regulations.

Loadsmart may use artificial intelligence (AI) tools during the hiring process to support tasks such as reviewing applications, analyzing resumes, or assessing responses. These tools assist our recruitment team but do not replace human judgment. Final hiring decisions are made by humans.