Sales Enablement & Operations Director (Chicago)

Ready to drive revenue, streamline sales processes, and empower a high-performing team? We’re looking for a Sales Enablement & Operations Director to join our growing multi-disciplinary Client Solutions team and lead processes and systems that fuel Cresa’s success.
As the Sales Enablement & Operations Director, you’ll be at the center of our go-to-market strategy—building scalable processes, managing new project intake, tracking client engagements and deadlines. You’ll work cross-functionally with Client Solutions leadership, advisors, service line leaders, technology and research to ensure our teams are fully equipped to convert opportunities into long-term client relationships.

Responsibilities

• Lead and manage the new project intake process, to help qualify, triage, and prioritize requests ensuring all pursuits are properly scheduled and resourced
• Track proposal milestones, deadlines, and submissions, coordinating with Solutions and Pursuit Teams to ensure teams are fully supported in delivering timely, compliant, and thorough responses
• Champion continuous process improvement.
• Develop sales forecasts and manage performance reporting using CRM and analytics tools
• Drive CRM adoption and data integrity (e.g., Salesforce), ensuring accurate pipeline and performance metrics
• Collaborate with Finance and Solutions Teams to collect data and create reporting for C-Suite and Leadership team
• Analyze sales trends to identify gaps, risks, and opportunities for growth
• Conduct win/loss debriefs and analysis
• Responsible for Solutions Team onboarding, knowledge management, and ongoing training programs
• Oversee core sales systems (e.g., Salesforce, Smartsheet, Tableau, Power BI), ensuring they support team efficiency, reporting accuracy, and pipeline visibility
• Facilitate sales certifications, workshops, and coaching programs that boost sales effectiveness

Strategic Impact

• Serve as a key advisor to Solutions Team leadership, delivering insights that shape go to market strategy and revenue growth
• Track and report enablement KPIs such as time-to-productivity, proposal win rates, and debrief feedback

Qualifications

• 7+ years of experience in sales enablement, sales operations, or pursuit strategy—ideally in commercial real estate, professional services, or complex B2B sales
• Proven ability to manage high volume project intake, pursuit prioritization, and team workflows
• Strong proficiency in CRM and analytics platforms
• Exceptional communication, stakeholder management, and cross-functional leadership skills

Location: This position is based in Chicago, IL, but willing to consider other Cresa office locations or remote work on a case by case basis.