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Sales Development Representative- Chicago-

Project44 · Chicago, IL · Sales

Posted Aug 13, 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 a typical day when you were hitting your call and activity metrics. What did the number of dials, emails, and conversations actually look like for you?

whether the candidate has actually operated in a high-volume, metrics-driven cadence and can speak to real numbers

Tell me about a cold call that went badly. What happened and what did you do right after you hung up?

resilience and self-correction rather than a polished success story

Tell me about a time you used AI tools to improve your outreach or research on prospects. What was the actual result?

genuine hands-on AI fluency versus a buzzword answer

Tell me about the toughest quota or target you've had to hit and whether you made it.

honesty about performance under pressure and comfort discussing quota history directly

Technical

What do you know about project44 and the supply chain visibility space, and who do you think we're competing against?

whether they did real homework on the product and market, not just the company name

Describe your experience with Salesforce and SalesLoft, or similar tools. What's a workflow or sequence you built or relied on daily?

hands-on familiarity with the specific tech stack versus generic CRM exposure

How do you decide which accounts in a CRM to prioritize for re-engagement versus which ones to let sit?

strategic thinking about account prioritization, not just working a list top to bottom

How do you keep yourself organized when you're juggling dozens of prospects at different stages at once?

time management and pipeline discipline for a high-volume role

What's something about selling enterprise SaaS or logistics software specifically that's different from other sales you've done?

whether they understand the complexity and buying cycle of enterprise software versus transactional sales

Situational

How would you qualify an inbound lead from project44's website in the first five minutes of a call?

understanding of basic qualification frameworks like BANT or MEDDIC and ability to think on their feet

Say you get a prospect who's mildly interested but keeps saying 'send me some info and I'll get back to you.' What do you actually do next?

objection handling skill and whether they let leads go cold or push for commitment

If you booked a meeting and later realized the prospect wasn't actually a good fit, what would you do about it?

integrity around lead quality versus just chasing meeting counts

This role requires being in the Chicago office four days a week and hitting daily activity numbers. How do you feel about that kind of structure and visibility into your day?

genuine fit with the in-office, closely tracked environment rather than surface-level agreement

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The full job description

As published by Project44.

<div class="content-intro">     </div>Why project44?  At project44, we believe in better.    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.    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.    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.    As a Sales Development Representative at project44, you will be responsible for inbound lead qualification and outbound prospecting within the North America region - into and through the sales funnel and setting up sales qualified appointments. You are held accountable by daily activity and call metrics along with quarterly quotas. You are a passionate and well-organized sales development representative with experience in selling enterprise software (SaaS). You are excited about the product you are representing and have the grit and tenacity required while succeeding in a fast-paced environment.<span class="EOP SCXW6817199 BCX8" data-ccp-props="{"134233117":false,"134233118":false,"201341983":0,"335551550":1,"335551620":1,"335557856":16777215,"335559685":0,"335559737":0,"335559738":240,"335559739":240,"335559740":278}">  AI at project44 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. 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. In-office Commitment: Our office is where ideas spark, connections thrive, and innovation comes alive. We are looking for candidates who are enthusiastic and committed to joining our team on-site, in our beautiful headquarters four days a week. Together, we’re building something extraordinarily learn, grow, and thrive in our fast-paced, transformative environment. Key Accountabilities <ul> <li>Evangelize project44 to prospects and qualify them for the sales team  </li> <li>Respond to requests from inbound leads in a timely manner and conduct qualification calls  </li> <li>Book qualified meetings with prospects for the sales team  </li> <li>Collaborate and iterate on inbound emails and messaging  </li> <li>Target and prioritize prospects within our CRM for re-engagement  </li> <li>Efficiently use Salesforce to research accounts, identify key contacts and reach out (cold call) to prospective customers  </li> <li style="font-weight: bold;">In-office Commitment: Our office is where ideas spark, connections thrive, and innovation comes alive. We are looking for candidates who are enthusiastic and committed to joining our team on-site, in our beautiful headquarters four days a week. Together, we’re building something extraordinary—learn, grow, and thrive in our fast-paced, transformative environment. </li> </ul> Requirements & Preferred Skills <ul> <li style="font-weight: bold;">Experience in demand gen or cold call sales in enterprise software, SaaS or logistics</li> <li>Competitive nature - should be eager to learn and win.</li> <li>Direct experience with Salesforce.com and SalesLoft a plus</li> <li>Superior pre-call planning, opportunity qualification, and objection handling skills</li> <li>Solid communications skills - both verbal and written</li> <li>Positive and energetic phone skills, excellent listening skills.</li> <li>Outstanding attention to detail with superior time and project management skills</li> <li>Experience using AI to enhance demand gen efforts and improve outreach in enterprise SaaS or logistics is a plus.<span class="EOP SCXW19837490 BCX8" data-ccp-props="{"134233117":false,"134233118":false,"201341983":0,"335551550":1,"335551620":1,"335557856":16777215,"335559737":0,"335559738":240,"335559739":240,"335559740":278}"> </li> </ul> Compensation and Benefits: 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 $45,000 – $65,000 plus commissions.  Diversity & Inclusion   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.   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.   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!   For any needed accommodations during the hiring process, please email <a href="mailto:recruiting@project44.com">recruiting@project44.com</a>. 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 requirements.   #LI-Hybrid <div class="content-conclusion">   </div>

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Sales Development Representative- Chicago-

Likely interview questions for this role

Practice this interview out loud.

The full job description

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