Senior Sales Director - Chicago

Senior Sales Director Location: Remote (must be based in Chicago) Territory: Central Compensation: $170,000–$180,000 base + OTE $300,000–$350,000 (uncapped commission) Travel: Up to 30% Overview We are seeking a high-performing Senior Sales Director to drive new-logo acquisition and expand our presence across priority US markets. This role is focused on selling high-value, consultative technology services to organizations that view software, data, and AI as strategic growth enablers—not just IT spend. You’ll lead complex pursuits in the $500K–$1M+ range across healthcare innovators, ISVs/SaaS, high-tech, enterprise, and businesses. From AI and data platforms to cloud modernization and full-scale engineering programs, you’ll connect client transformation goals to differentiated solutions that deliver measurable business impact. This is not a transactional sales role. We’re looking for a trusted advisor who can create urgency, map value, and influence C-suite decision-makers acceleration. What You’ll Do Own the full sales cycle for net-new logo acquisition across your East Coast territory Target US-based organizations with $100M–$2B in annual revenue Build and execute territory and account strategies that generate $3M–$5M+ in annual net-new services revenue Engage senior stakeholders including CIOs, CTOs, COOs, VPs of Product/Engineering, and PE operating partners Identify business inflection points (PE investments, leadership changes, platform modernization, AI initiatives) and convert them into actionable opportunities Position and sell complex, consultative offerings including AI/ML, data platforms, cloud modernization, QA automation, and software product engineering Apply MEDDPICC rigor to qualify deals and prioritize high-value, winnable opportunities Lead pursuit strategy and collaborate with solution architects and delivery leaders to develop proposals, SOWs, and contracts Represent the company at key client meetings, industry events, and conferences What You Bring 10+ years of experience selling technology services or consulting (nearshore/offshore experience preferred) Proven success closing $500K–$1M+ services deals with mid-market and enterprise clients Strong industry experience or networks within healthcare, SaaS/ISVs, or high-tech Solid understanding of client priorities across AI, data, cloud, and digital product transformation Executive presence and confidence engaging with complex, multi-stakeholder buying committees Experience selling into or alongside private equity-backed organizations and understanding value-creation drivers Collaborative co-selling experience with hyperscaler or channel partners (AWS, GCP, Azure, etc.) A consultative, outcome-driven sales approach focused on business impact and long-term partnerships Pluses (Nice to Have, Not Required) Background working in or selling to private equity-backed portfolios Strong working knowledge of AI-driven solutions and modern data platforms Domain expertise and go-to-market experience in healthcare, banking, financial services, or insurance Demonstrated ability to articulate complex technical concepts clearly to executive audiences Highly articulate, composed, and credible in C-level conversations Experience building thought leadership and trusted-advisor status within a defined territory Benefits & Perks 100% company-paid Medical, Dental, and Vision insurance 401(k) with generous company match Pre-tax FSA options Employer-paid Short- and Long-Term Disability Unlimited PTO plus paid parental leave Remote/hybrid flexibility Access to executive mentorship and long-term career growth opportunities #INDHP Job Type: Full-time Pay: $170,000.00 - $350,000.00 per year Benefits: 401(k) 401(k) matching Dental insurance Flexible schedule Paid time off Application Question(s): Please list your experience with hard core consultative sales approach into enterprise/midmarket sized companies Education: Bachelor's (Required) Experience: selling technology services : 10 years (Required) Proven success closing $500K–$1M+ services deals: 3 years (Required) AI, data, cloud, and digital product transformation: 3 years (Required) Work Location: Remote