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Ore Macaulay

Ore Macaulay

Sales Enablement

Talent
Chicago, City of Chicago, CookMember since January 29, 2025
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About

Results-driven operations leader with 8+ years of experience in sales enablement and process transformation across regulated industries. Lean Six Sigma and ITIL-certified professional with proven expertise in developing revenue- generating training programs, implementing strategic initiatives, and driving operational excellence through data-driven methodologies. Track record of delivering measurable business outcomes through innovative learning solutions and change management.

Experience

Learning & Process Optimization Manager Jun 2021 - Present

Generated $7M+ in revenue growth through implementation of new sales methodology through training and enablement program, achieving 30% revenue growth and 27% improvement in process adoption

Scaled GTM operations by designing company's first structured sales onboarding program, reducing ramp time by 45 days and improving new hire productivity by 15%

Achieved 95% adoption rate of new customer success processes by executing change management strategy across 120+ GTM stakeholders

Orchestrated annual Sales Summit, driving 40% increase in pipeline generation through strategic alignment of cross- functional initiatives

Claims Enablement Specialist Sep 2019 - May 2021

Program managed mission-critical CMS migration from legacy system to CMS platform for over 300 users; orchestrated end-to-end implementation including technical deployment, development of process and SOPs documentation, creation of comprehensive training curriculum, and stakeholder alignment across 5 business units, resulting in 98% user adoption within 60 days and 20% improvement in data quality

Led transformation of process workflow, reducing prospect-to-close timeline by 22% and improving team efficiency Developed and deployed sales coaching framework resulting in 20% reduction in sales cycle time and 15% increase in win rates

Claims Sales Analyst Jul 2016 - Sep 2019

Managed $15M+ claims portfolio while consistently exceeding SLAs and maintaining 28% higher customer satisfaction than team average

Identified and capitalized on coverage gap opportunities during claims process, generating an average of $450K annually in new policy sales

Led cross-functional initiative to optimize claim workflow processes, reducing cycle time by 17% and improving team productivity by 22%

Enterprise Account Specialist Aug 2013 - Jun 2016

Managed portfolio of 150+ high-value accounts ($250K+ premiums), driving retention through consultative relationship building and proactive risk solutions

Increased settlement acceptance rate by 35% through a consultative approach and value-based negotiation strategies

Education

I hold an MBA with an IT Management specialization and a BA in Political Science

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