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Artificial Intelligence • Marketing Tech • Software • Generative AI • Automation
The Sales Director will lead an Enterprise Sales team, drive market growth, optimize sales strategies, and enhance customer experiences while collaborating with other leaders.
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The Director of Sales for Mid-Market West will lead commercial activities in their region, develop strategic sales plans, build client relationships, and grow channel partnerships targeting employers with under 5,000 employees.
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The Director of Sales manages a SMB sales team, develops sales strategies, drives performance, builds customer relationships, and leads account development, all to enhance revenue and markets.
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About Us:
Docsumo is Document AI software that helps enterprises automate document processing. We help enterprises convert documents such as invoices, bank statements, tax returns & other unstructured docs into actionable data. We are backed by Fifth Wall, Common Ocean VC, Sequoia, Barclays, Techstars & Better Capital.
As a Director - Sales, you will be leading the Sales team. You will be working with the founders to deliver on the team quota.
Responsibilities
- Lead a team of sales professionals to drive revenue
- Recruit, train, motivate, build pipeline, market via webinars/events, build playbooks, analyze data.
- Prepare and deliver presentations/demos and proposals to tech buyers in the US.
- Manage the entire sales cycle from prospecting to closing for the each
- Develop long-term strategic relationships with key accounts and ensure client satisfaction
- Track, analyze, and report key qualitative feedback & quantitative metrics back to the organization
- Strong leadership and management skills, with the ability to lead and motivate a sales team
- Build and set OKRs and KRAs for individuals and for the team
Requirements
- Highly self motivated and entrepreneurial, with experience in leading and managing sales teams in a distributed environment
- 8+ years of experience in B2B sales, with 3+ years in a leadership position
- Proven track record of meeting sales quota consistently
- Must be an exceptional communicator, whether verbally – on the phone, or written – through the email
- Should be able to work USA East Coast timings (8am to 5pm)
- Proficient in English & with understanding of USA culture
- Should have prior experience working with C level executives
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



