Jobs › Project44

Sales Development Representative- Chicago-

Project44 · Chicago, IL · $45,000–$65,000 a year · Sales

Posted Sep 28, 2026 · We last checked this listing on Oct 6, 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.

About your past

Tell me about a time you faced a lot of rejection. How did you keep going?

What they are checking: Whether they have the resilience SDR work demands day after day.

Tell me about a goal you set for yourself and how you tracked your progress.

What they are checking: Whether they are self-driven and comfortable being measured on activity and results.

Tell me about a time you got feedback that stung. What did you do with it?

What they are checking: Whether they are coachable, which decides how fast an SDR improves.

What would you do

Give me a 30-second cold call opener to a VP of Logistics at a manufacturer.

What they are checking: Whether they can get to a relevant problem fast instead of reading a product pitch.

The prospect says they're happy with their current visibility provider. What do you say next?

What they are checking: Whether they can handle a common objection with curiosity instead of pushing harder.

How would you use AI tools to prospect more effectively without sounding like a robot?

What they are checking: Whether they use AI with judgment, as the company expects from every role.

How do you organize your day between calls, emails and LinkedIn?

What they are checking: Whether they can manage time and volume in a structured way.

About the work

In your own words, what does project44 sell, and who is the buyer?

What they are checking: Whether they did their homework and can explain supply chain visibility simply.

How would you research an account before reaching out?

What they are checking: Whether they personalize outreach using what a company ships and how, rather than blasting templates.

What makes a meeting you book a good meeting for an Account Executive?

What they are checking: Whether they understand qualification and care about pipeline quality, not just meeting counts.

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.

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 • Evangelize project44 to prospects and qualify them for the sales team    • Respond to requests from inbound leads in a timely manner and conduct qualification calls    • Book qualified meetings with prospects for the sales team    • Collaborate and iterate on inbound emails and messaging    • Target and prioritize prospects within our CRM for re-engagement    • Efficiently use Salesforce to research accounts, identify key contacts and reach out (cold call) to prospective customers    • 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.   Requirements & Preferred Skills • Experience in demand gen or cold call sales in enterprise software, SaaS or logistics • Competitive nature - should be eager to learn and win. • Direct experience with Salesforce.com and SalesLoft a plus • Superior pre-call planning, opportunity qualification, and objection handling skills • Solid communications skills - both verbal and written • Positive and energetic phone skills, excellent listening skills. • Outstanding attention to detail with superior time and project management skills • 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}">  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  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 requirements.    #LI-Hybrid

Apply at Project44

Sales Development Representative- Chicago-

Likely interview questions for this role

Practice this interview out loud.

The full job description

More sales development representative roles

Related jobs

Sales Development Representative

Sales Development Representative

Sales Development Representative (Entry Level)

Sales Development Representative (Entry Level)

Sales Development Representative (Entry Level)

Sales Development Representative