JobsProject44

Enterprise Account Executive

Project44 · Chicago, IL · Sales

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

Apply at Project44

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 largest enterprise deal you've closed, from first contact to signature. What made it complex?

whether the candidate has real experience managing long, multi-stakeholder SaaS sales cycles versus shorter transactional deals

Tell me about a deal where you had to sell across IT, procurement, and transportation or supply chain stakeholders at the same time. How did you keep everyone aligned?

comfort navigating multi-threaded enterprise sales with competing priorities across lines of business

Give me an example of when you missed a quarterly number. What happened and what did you change afterward.

honesty and self-correction habits when facing shortfall, not just success stories

How do you personally define and run a hunting motion versus managing an existing account? Give me a specific example of new logo work you originated yourself.

whether the candidate actually generates net-new pipeline or mainly works warm accounts

Tell me about a time a customer pushed back hard on price or a competitor's offer. How did you handle it and what was the outcome?

negotiation skill and ability to defend value rather than default to discounting

Tell me about the last time you brought customer feedback back to a product team. What was the feedback and what happened with it?

whether the candidate sees themselves as a customer advocate internally, not just a closer

Technical

What do you know about how supply chain visibility platforms like ours differ from a traditional TMS or EDI-based tracking setup?

depth of real domain knowledge in logistics technology versus surface-level familiarity

How do you research and understand a large shipper's organizational structure before you ever get a meeting?

rigor of account planning and pre-call preparation habits

What sales methodology have you been trained in, and how do you actually use it day to day rather than just in theory?

whether formal sales process training translates into a repeatable working discipline

Situational

Say you've inherited a territory of top-tier shipper accounts with almost no existing pipeline. Walk me through how you'd build your territory business plan for the first ninety days.

ability to structure account strategy and prioritize from scratch rather than relying on inherited pipeline

A prospect's transportation team loves the product, but their IT security team is stalling on a data integration question you can't answer. What do you do next?

instinct to loop in pre-sales engineering and value engineering rather than guessing or stalling the deal alone

You're presenting to a room of VP and C-level supply chain leaders who have never heard of project44. How do you structure that pitch differently than a working-level demo?

ability to adapt messaging and executive presence for senior audiences

How do you decide which deals in your pipeline get your time this week versus which ones wait?

forecasting discipline and ability to prioritize a large enterprise portfolio realistically

Practice this interview out loud.

Offer builds a real interview for this exact role at Project44 from your resume and this job description, asks the questions one at a time, and tells you what landed. The first one is free.

Practice this out loud

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>

Apply at Project44

Related jobs

Enterprise Account Executive

Project44 · Chicago, IL

Posted Aug 3 · Verified Sep 20

Senior Software Engineer

Project44 · Chicago, IL

Posted Sep 11 · Verified Sep 20

Staff Platform Product Manager, Movement

Project44 · Chicago, IL

Posted Sep 9 · Verified Sep 20

Director of Product Operations

Project44 · Chicago, IL

Posted Sep 2 · Verified Sep 20

Senior Manager of Product Commercialization/GTM

Project44 · Chicago, IL

Posted Sep 1 · Verified Sep 20

Senior Forward Deployed Engineer

Project44 · Chicago, IL

Posted Aug 26 · Verified Sep 20