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Enterprise Sales Executive

Mastery Logistics SystemsLake Forest, Illinois, United States | Minneapolis, Minnesota, United States | Omaha, Nebraska, United StatesRemote, Onsite

Mastery Logistics Systems is revolutionizing the transportation and supply chain industry with 
Mastermind, the world’s first 

lovable

 Transportation Management System (TMS). We empower large transportation companies and shippers with a single platform to manage diverse operations, enabling flexibility, visibility, control, and efficiency.
Our team is a diverse and collaborative group committed to solving big challenges with innovation and creativity. We’re building a system that helps the transportation industry work smarter and more efficiently while making meaningful impacts on the global economy.Join us in our mission to create something extraordinary—

let’s build a masterpiece!


Position Overview


As an Enterprise Sales Executive, you will play a key role in expanding Mastery’s footprint by identifying, engaging, and closing high-value enterprise clients. You’ll collaborate with senior decision-makers, understand their business challenges, and demonstrate how Mastermind delivers measurable results.

What You’ll Do


  • Develop and Execute Sales Strategies
  • Identify, target, and engage potential enterprise customers in the logistics, supply chain, and transportation sectors.
  • Build and maintain a strong pipeline of high-value opportunities, driving the sales process from prospecting to close.
  • Engage and Influence Key Decision-Makers
  • Establish relationships with C-level executives and key stakeholders to position Mastery as the preferred solution.
  • Conduct in-depth discovery to understand customer needs and craft tailored solutions.
  • Manage the Full Sales Cycle
  • Lead complex, multi-stakeholder sales processes, including presentations, negotiations, and contract execution.
  • Collaborate with internal teams (product, marketing, and customer success) to ensure seamless client engagement and implementation.
  • Achieve and Exceed Sales Targets
  • Consistently meet and exceed revenue goals and key performance metrics.
  • Stay ahead of industry trends and competitor offerings to maintain a competitive edge.

What We’re Looking For


  • Proven Sales Success: 5+ years of experience in enterprise sales, preferably in SaaS, logistics, transportation, or supply chain solutions.
  • Industry Expertise: Strong understanding of logistics and supply chain management; an existing network within the industry is a plus.
  • Consultative Selling Skills: Ability to conduct deep discovery, align solutions with customer needs, and articulate ROI.
  • Strategic Thinking: Experience managing long sales cycles with multiple stakeholders and complex negotiations.
  • Self-Starter Mentality: Highly motivated, results-driven, and comfortable working independently in a fast-paced environment.
  • Tech-Savvy & Product Knowledge:Strong understanding of cloud-based SaaS platforms, APIs, databases, AI/ML, etc. and how they power modern logistics solutions. Ability to confidently discuss technical concepts with clients and collaborate effectively with product and engineering teams."

Why Join Mastery Logistics Systems?


  • Innovative & Impactful Work – Be part of a company that is transforming the logistics industry with cutting-edge technology.
  • Growth & Career Development – Join a fast-growing company with opportunities for professional advancement.
  • Competitive Compensation – Base salary plus uncapped commission and performance-based incentives.
  • Strong Company Culture – Work with a collaborative, driven, and passionate team that values innovation and excellence.

Estimated Compensation:$130,000 - $180,000 base salary per annum, plus commission (commensurate with experience and ability)

About Mastery


Mastery Logistics Systems is building the world’s first lovable Transportation Management System, or TMS.Our customers – large transportation companies and shippers who need those companies – have struggled with systems that are outdated or inadequate. As shippers or transportation service providers, our customers have in the past been forced to use multiple systems to manage dedicated fleet operations, outsourced or insourced trans management, one way trucking, truckload brokerage, LTL, and Intermodal, or to sub-optimize one or more of those functions by attempting to fit it into a TMS that is adequate at another function.Mastermind TMS allows our customers to bring all of these functions into a single platform, providing flexibility, visibility, control, and efficiency.

Today’s unprecedented global supply chain upheavals underscore how important the transportation industry is. We are building a system to allow this industry to work faster, smarter and more efficiently.The challenges in this industry are big and exciting! We are tackling everything from fast and efficient data input to ingesting large amounts of data and applying AI to looking at blockchain to securely digitize paperwork. If you are passionate about humanizing an industry, automating in innovative ways, building for quality and scale, helping make people's lives easier and touching every part of our economy then this is the place for you.Mastery Logistics Systems is committed to continuing to build an incredible company. We are a masterful mosaic of incredible people. We are specialists and experienced in our respective fields. We are dedicated to continuous improvement both professionally and personally. We are a collective group of really good people. We have different interests, backgrounds & talents and we work together to create really cool stuff! We believe in diversity of thought and are mindful and inclusive. We have deep respect for each other and work diligently at adding the right people to our teams.We have flexible schedules but share in the mission that we are building and need to get it done. We offer an excellent suite of benefits.Our team has the domain knowledge and connections to make an impact, and we’re looking for experienced and thoughtful people to who thrive on creating and building great products. We want people who have a true passion for servicing and taking care of our customers. We need people who are flexible problem solvers, thrive on collaboration and consistently know how to communicate their solutions well. We are small and nimble – which is evident in how quickly we could pivot to our new reality. Each member of the team can make a tremendous impact both technically and culturally. While a start-up, we are well-funded, have an initial paying customer with which to test and launch, and are founded by top experts and veterans in the logistics industry.Join us – you’ll love it – let’s build a masterpiece!

Benefits


Mastery takes great pride in providing our employees a robust and highly competitive benefit package. Our benefits include Medical, Dental and Vision insurance, company paid Life insurance for 1x salary, Legal, AD&D, Additional Life and other employee assistance benefits. We have a 401k savings plan with a 4% match. We provide opportunities for professional growth and development. We have a manage your life and schedule Paid Time Off program. We are fully devoted to finding creative perks and benefits since we cannot currently enjoy our cool office culture.

Our philanthropic partner is St. Jude Children’s Research Hospital.We are an equal opportunity employer and actively seek a diverse community of professionals. 

Life at Mastery Logistics Systems

Mastery is on a Mission to empower select shippers, carriers and logistics companies to thrive in complexity. Mastery brings to market MasterMind™, a cloud-based SaaS technology solution for large complex organizations, built to fuel automation, visibility, and productivity within their supply chains. Mastery was conceived by Jeff Silver, whose proprietary technology systems have powered some of the largest logistics companies in North America for over four decades and have been brought to life by a team of logistics and software professionals – true Maestri at work. MasterMind is built for size, stability, speed, efficiency, and automation within and across functional areas. Built by logistics experts, MasterMind provides unprecedented visibility and control by embracing the complexity that is the reality of the supply chain world. For more than 40 years, the industry has grown with patchwork tools built for specific jobs. And complexity continues to soar. Supply Chains have generally been disconnected, and disconnected systems force manual intervention to deliver desired results. With multiple tools and multiple work streams, labor and IT costs compound with no guarantee of a single view into a given Supply Chain. Waste and inefficiency abound. When multiple systems are used to manage operational activity across business units, workstreams and networks, it creates complexities that can be challenging to manage and costly to manage. Companies often sub-optimize one or more of those functions by attempting to fit it into a transportation management system that is adequate at another function, creating friction between systems or added work. Mastery solves this problem by bringing all operating functions into a single cloud-based TMS, providing flexibility, visibility, control, and efficiency. We can all work faster, smarter, and more efficiently with Mastery.
Thrive Here & What We Value- Commitment to building an incredible company with a diverse team- Seeking experienced individuals who thrive on creating great products- Belief in diversity of thought and inclusivity- Deep respect among employees- Competitive benefit package (Medical, Dental, Vision insurance; Company paid Life insurance for 1x salary; Legal, AD&D, Additional Life)- Employee assistance benefits- Opportunities for professional growth and development

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