JobsProject44

Enterprise Account Executive

Project44 · Chicago, IL · Sales

Posted Aug 3, 2026 · We last checked this listing on Sep 20, 2026

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Likely interview questions for this role

Written from this job description, not a generic list. Each one notes what the interviewer is really checking.

Behavioral

Walk me through the biggest enterprise deal you've closed, from the first conversation to signature. What made it complex?

whether they've actually run a full complex SaaS sales cycle at the size and scope this role requires

Tell me about a deal where you had to sell across multiple stakeholders, say IT, procurement, and transportation, who all wanted different things. How did you get them aligned?

experience navigating multi-threaded enterprise buying committees, which the posting flags explicitly

Tell me about a time you missed quota. What happened and what did you change afterward?

self-awareness and resilience given the explicit $1M+ quota requirement

Tell me about a time a deal stalled because you couldn't get access to the actual decision maker. What did you do?

persistence and creativity in navigating enterprise gatekeeping

Describe a time you had to work closely with pre-sales engineering or a value engineering team to win a deal. What was your role versus theirs?

ability to operate as the account owner in a team selling motion rather than working solo

You're in front of a room of senior logistics leadership at a shipper doing a formal presentation. Tell me about a similar high-stakes presentation you've given and how it went.

comfort and skill presenting to executive audiences, called out directly in the requirements

Technical

How do you think about the difference between selling supply chain visibility software versus a typical horizontal SaaS product?

genuine domain knowledge in logistics and supply chain versus generic SaaS sales talk

What do you know about how project44 differentiates from competitors like FourKites or Overhaul, and how would you position that in a sales conversation?

whether they did real homework on the competitive landscape rather than a surface-level pitch

How would you explain the role of EDI and blockchain in supply chain visibility to a prospect who's skeptical of new technology?

whether stated industry knowledge is real and can be communicated simply to a non-technical buyer

How do you use AI tools in your day-to-day sales work right now, like prospecting, account research, or deal prep?

actual fluency with AI tools versus a rehearsed answer, given the company's explicit AI expectations

Situational

Say you're given a territory of top-tier shippers and told to build a business plan from scratch. Walk me through how you'd prioritize accounts and build pipeline in the first ninety days.

whether they can construct a real territory strategy rather than just react to inbound leads

A prospect's procurement team says your pricing is too high compared to a competitor bid. How do you handle that conversation without just discounting?

negotiation discipline and ability to defend value rather than default to price concessions

A key champion at a top account you've been developing suddenly leaves the company mid-deal. What's your next move?

ability to recover and rebuild relationships when enterprise deals lose their internal advocate

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The full job description

As published by Project44.

<div class="content-intro"><p>&nbsp;</p> <p>&nbsp;</p> <p>&nbsp;</p></div><p><strong>Why project44?</strong></p> <p>At project44, we believe in better.</p> <p>We challenge the status quo because we know a better supply chain isn’t just possible—it’s essential. Better for our customers. Better for their business. Better for the world.</p> <p>With our Decision Intelligence Platform, Movement, we’re redefining how global supply chains operate. By transforming fragmented logistics data into real-time, AI-powered insights, we empower companies to connect instantly, see clearly, act decisively, and automate intelligently. Our Supply Chain AI enhances visibility, drives smarter execution, and unlocks next-gen applications that keep businesses moving forward.</p> <p>Headquartered in Chicago, IL with a 2nd HQ in Bengaluru, India we are powered by a diverse global team that is tackling the toughest logistics challenges with innovation, urgency, and purpose. If you’re driven to solve meaningful problems, leverage AI to scale rapidly, drive impact daily, and be part of a high-performance team – we should talk.</p> <p>We expect every project44 team member, regardless of role or function, to actively leverage AI in their day-to-day work. Whether you're building product, serving customers, managing people, or running operations, AI is a tool you're expected to use with intent, curiosity, and judgment. We don't expect everyone to be a data scientist. We do expect everyone to be an intelligent user of AI: able to identify where it adds value, direct it effectively, evaluate outputs critically, and govern it responsibly. We invest in our team's AI fluency because we believe it's a competitive advantage for every person at project44, not just our engineers.&nbsp;</p> <p><strong>Description</strong></p> <p>As a  Strategic Account Executive, you will work cross-functionally with our lead generation, pre-sales engineering and value engineering teams to position project44 within our target market’s supply chain technology. You will be the owner of the accounts and territory. As such, you will develop and execute a comprehensive territory business plan which details account strategies and the specific way in which you will exceed your goals.  This will include the detailed understanding of the customer’s organizational structure and clear understanding of how you will gain alignment with all key stakeholders.</p> <p>You are an energetic, self-starter.  You are a highly effective communicator both internally and externally to customers, prospects and partner.  You have track record of over-achievement, a positive outlook, proven and demonstrative hunting capabilities with the ability to think strategically. Your style is considered consultative in nature and your process allows you to clearly understand the prospects business needs and help provide the solutions.</p> <p><strong>Key Accountabilities</strong></p> <ul> <li>Develop detailed sales plans and sales forecasts</li> <li>Travel to meet with clients, prospects and partners</li> <li>Manage a large portfolio of enterprise accounts</li> <li>Consistently meet quarterly and annual targets</li> <li>Understand competitive solutions and project44 differentiators</li> <li>Drive active sales cycles while building new business pipeline through prospecting and relationship building with top tier Shippers</li> <li>Be the leader, manage and direct a sales strategy that allows for customer, channel and project44 to win</li> <li>Summarize product feedback gathered from customer meetings and act as advocate for our customers with internal development and product teams</li> <li>Maintain up to date knowledge of logistics industry, EDI, and blockchain</li> <li>Ability to sell across multiple Lines of Business simultaneously (IT, Procurement, Transportation, Supply Chain/Logistics)</li> </ul> <p><strong>Requirements &amp; Preferred Skills</strong></p> <ul> <li>Experience selling Supply Chain SaaS Software or Complex SaaS Solutions</li> <li>Experience in a fast-growth technology company</li> <li>Comfortable delivering presentations to leadership and large groups</li> <li>Strategic thinking combined with a hands-on approach to achieve objectives</li> <li>Highly organized with a sense of urgency to meet deadlines consistently</li> <li>Willingness to travel for key customer meetings and events</li> <li>Strong understanding of the supply-chain and logistics space is highly preferred</li> <li>Ability to thrive in a dynamic, fast-paced, entrepreneurial environment and consistently deliver results</li> <li>Proven track record of meeting or surpassing an annual quota of $1M+</li> <li>Successfully developed a pipeline and closed $500k and above in the top accounts in the region</li> <li>Previous sales process and methodology training</li> <li>BA/BS or equivalent educational background </li> <li> <ul> <li><strong><span style="text-decoration: underline;">In-office Commitment:</span> </strong>Our office is where ideas spark, connections thrive, and innovation comes alive. We are looking for candidates who are enthusiastic and committed&nbsp;to joining our team on-site, <u>in our beautiful headquarters four days a week</u>.&nbsp;Together, we’re building something extraordinary—learn, grow, and thrive in our fast-paced, transformative environment.</li> <li><strong><span style="text-decoration: underline;">Relocation offered:</span> </strong>We’re proud to call Chicago home - a walkable downtown, amazing food, and a team that makes big ideas move fast.&nbsp; And&nbsp;we’re ready to help you make it yours,&nbsp; project44 offers relocation assistance for team members joining us from outside the area.&nbsp;</li> </ul> </li> </ul> <p><strong>Compensation and Benefits:</strong></p> <p>We continually evaluate our pay ranges to reflect skills, experience, and market conditions. The base salary offered will be determined by assessing a candidate's experience and skills relative to the scope and responsibilities of the position, as well as the specific geographic location where the job will be performed. Base salary is one component of project44's total compensation package, which also includes stock options for all EOR and project44-employed team members, bonus or commission eligibility depending on role, and a benefits package tailored to your country of employment. Specific benefits package offerings vary by country and may include health, dental, and vision coverage, retirement plans, and paid time off, in line with local market standards and statutory programs. The base salary range for this position is $120,000 – $190,000 plus commission USD.</p> <p><strong>Diversity &amp; Inclusion:</strong></p> <p>At project44, we're designing the future of how the world moves and is connected through trade and global supply chains. As we work to deliver a truly world-class product and experience, we are also intentionally building teams that reflect the unique communities we serve. We’re focused on creating a company where all team members can bring their authentic selves to work every day.</p> <p>We’re building a company that every one of us at project44 is proud to work for, and our journey of becoming a more diverse, equitable and inclusive organization, where all have a sense of belonging, is shaped through the actions of our leadership, global teams and individual team members. We are resolute in our belief that each team member has an equal responsibility to mold and uphold our culture.</p> <p>project44 is an equal opportunity employer seeking to enrich our work environment by creating opportunities for individuals of all backgrounds and experiences to thrive. If you share our values and our passion for helping the way the world moves, we’d love to review your application!</p> <p>For any accommodation needed during the hiring process, please email recruiting@project44.com. Even if you don’t meet 100% of the above job description you should still seriously consider applying. Studies show that you can still be considered for a role if you meet just 50% of the role’s requirements.</p> <p>A candidate will be asked to conduct a pre-employment criminal back ground screening test as a standard routine to minimize moral &amp; integrity risks among our staff and to ensure Project44 is compliant with its internal pre-employment screening policy and SOC 2, Sarbanes Oxley Act and ISO 27001 compliance. We will only ask you to conduct a criminal background check when we</p> <p>believe it is proportionate to the role that you will fulfil within your team and/or department A criminal back ground check will be facilitated by our third party vendor Accurate who will assist you to get the appropriate documents from authorities in the country where you will be employed. Depending on the country where you will be employed your local authority will provide a Certificate of Conduct or similar document upon your request. If there are any costs related to screening, these will be borne by Project44. When our vendor Accurate will reach out to, you will be asked for your consent. We would like to emphasize that at all time you can decide to withdraw from the application process and/or to withdraw the consent to perform a screening test.</p><div class="content-conclusion"><p>&nbsp;</p> <p>&nbsp;</p></div>

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