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project44

Senior Director, Deal Desk

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Hybrid
Chicago, IL
Hybrid
Chicago, IL

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About Project44: Project44 is the world’s leading AI first, advanced visibility platform for shippers and logistics service providers. Trusted by thousands of global brands, Project44 connects, automates, and provides real-time insights across transportation modes including road, rail, ocean, air, and parcel. As a high-growth scale-up backed by top-tier investors, we are driving digital transformation across one of the world's most essential industries. 

By connecting the world's largest logistics data ecosystem, we're not just optimizing supply chains – we're empowering businesses to deliver on their promises, reduce costs and build more resilient operations. Recognized as a 5-time Leader in Gartner's Magic Quadrant and a Google Cloud Partner of the Year, our diverse global team is revolutionizing how products move around the world.

If you’re eager to be part of a winning team that works together to solve some of the most challenging supply chain challenges every day, let’s talk.

About the Role:

 

We are building a world-class Revenue Operations team to enable our next stage of growth, and our Deal Desk is at the forefront of driving revenue. As the leader of our Deal Desk team, you will work closely with Sales, Professional Services, Sales Operations, Finance, and Legal to build a streamlined and scalable quote-to-cash process.

Your responsibilities will include:

  • Build out a high-performing global deal desk team responsible for designing deal structures and efficiently coordinating deal flows
  • Analyze and develop deal structures and deal strategy in collaboration with Sales, Finance, Services, and Legal
  • Identify and implement optimizations to our quoting and approval processes, targeting a shorter deal cycle
  • Serve as a trusted advisor to Sales in structuring complex deals and enable them to navigate their deals through guidance and training
  • Own our quoting systems and drive necessary systems updates with IT and other stakeholders

Personal qualities to succeed in the role:

  • You are a builder and thrive when given the opportunity to develop your own strategy, processes, and people.
  • You are a talent-first leader who builds a strong team culture and has an exponential impact on your team members’ development.
  • You balance process optimization and trackability with immediate business needs and agility.
  • You prioritize data driven decisions and apply those to ambiguous situations.
  • You excel at collaborating cross-functionally with sales, finance, and other team members around the world.

Key Qualifications:

 

  • 10+ years experience with Deal Desk, Deal Strategy, Sales, and/or Sales Operations in a fast-paced B2B tech company, SaaS experience a plus
  • Track record of building out key deal desk processes from scratch
  • 5+ years' experience hiring, managing, and coaching team membersExperience leading and collaborating with teams across multiple geographies
  • Strong executive communication skills with extensive experience collaborating with C-suite executives BA/BS or equivalent educational background
  • Our office is where ideas spark, connections thrive, and innovation comes alive. The expectation is to be on-site, in office three days a week as this offers the chance to immerse yourself in the energy of our headquarters, collaborate with the founder, and experience our new customer experience center. Together, we’re building something extraordinary—learn, grow, and thrive in our fast-paced, transformative environment.
HQ

project44 Chicago, Illinois, USA Office

Located in the iconic art deco Merchandise Mart with impressive views of the Chicago river. The neighborhood is home to some of Chicago's best restaurants, retail, and is accessible by public transit.

What you need to know about the Chicago Tech Scene

With vibrant neighborhoods, great food and more affordable housing than either coast, Chicago might be the most liveable major tech hub. It is the birthplace of modern commodities and futures trading, a national hub for logistics and commerce, and home to the American Medical Association and the American Bar Association. This diverse blend of industry influences has helped Chicago emerge as a major player in verticals like fintech, biotechnology, legal tech, e-commerce and logistics technology. It’s also a major hiring center for tech companies on both coasts.

Key Facts About Chicago Tech

  • Number of Tech Workers: 245,800; 5.2% of overall workforce (2024 CompTIA survey)
  • Major Tech Employers: McDonald’s, John Deere, Boeing, Morningstar
  • Key Industries: Artificial intelligence, biotechnology, fintech, software, logistics technology
  • Funding Landscape: $2.5 billion in venture capital funding in 2024 (Pitchbook)
  • Notable Investors: Pritzker Group Venture Capital, Arch Venture Partners, MATH Venture Partners, Jump Capital, Hyde Park Venture Partners
  • Research Centers and Universities: Northwestern University, University of Chicago, University of Illinois Urbana-Champaign, Illinois Institute of Technology, Argonne National Laboratory, Fermi National Accelerator Laboratory

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