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Olaoluwa Ayesa has a diverse work experience spanning several industries and roles. Starting in 2008, they worked as a Project Management Officer at RTHG Services Ltd. From 2010 to 2011, they held the role of Senior Business Executive at GB Pharma LTD, where they were responsible for trade marketing and healthcare channels. In 2012, they became an Enterprise Sales Account Manager at Telnet Nigeria Limited, focusing on building relationships with financial services institutions and selling CRM and enterprise business solutions. In 2014, they joined JNC International Limited as a Regional Key Account Manager, where they were involved in defining product portfolios, managing key accounts, and identifying new business opportunities. From 2016 to 2021, they worked as a Sales Coach and Trainer at The Sales Training Academy, and as the Head of Product Strategy, Business Development, and Marketing for Africa at Sproxil. In 2019, they also served as a Volunteer Faculty and Training Facilitator at FATE Foundation. Currently, they hold the position of Head of Marketing and Product Growth/ Director at RedCloud since March 2022.

Olaoluwa Ayesa has a diverse education history. In 2014, they obtained a Master of Business Administration (MBA) degree with a specialization in Marketing Management from the University of Lagos. In the same year, they also earned a Certificate in Strategic Management and Enterprise Development from the Lagos Business School, Pan-Atlantic University.

Moving chronologically, Olaoluwa Ayesa pursued further education in 2016 and 2017. During this time, they obtained a CIM Level 6 - Professional Diploma from the Chartered Institute of Marketing (CIM) with a focus on Strategic Marketing and Innovation. Olaoluwa also attended the Lagos Business School, Pan-Atlantic University to study Managerial Leadership in Sales and Marketing.

In 2018, Olaoluwa Ayesa participated in the +Acumen Sales Leaders Program in Kenya, where they focused on Managing Markets and Customers. Subsequently, in 2019, they completed a course in Driving Strategic Innovation and Business Development at the Lagos Business School, Pan-Atlantic University.

Moreover, Olaoluwa Ayesa pursued additional education outside traditional institutions. Olaoluwa received a Mini MBA in Business Management and Innovation from the Tekedia Institute, although the specific dates are not provided.

To complement their academic achievements, Olaoluwa Ayesa obtained several certifications. In 2022, they acquired an Advanced Digital Marketing Certification from Wild Fusion Digital Centre. Olaoluwa also completed a Data Science Fellowship at Utiva in 2021 and obtained Verified International Academic Qualifications from World Education Services in the same year. In 2020, they earned certifications in Agile Product Management from Utiva, Advanced Brand and Product Management from BMA Nigeria, Business Lessons - Leadership, Sustainable Business Strategy and Management from Harvard Business School, and Design Thinking: Re-Modelling Business for Growth from the Lagos Business School, Pan-Atlantic University - Enterprise Development Center. Additionally, they participated in the Virtual Skills Lab | Coronomics: Resilience in the Global Pandemic Economy organized by Hult International Business School in 2020. In 2019, Olaoluwa Ayesa received a certification in Financial Forecasting and Cost Management from the African Management Institute and GS1 Global Standards in Healthcare and Pharmaceutical Supply Chain and Traceability from GS1. Finally, in 2018, they completed the African Sales Leaders Program - Managing Markets and Customers offered by Acumen, and in 2016, they obtained a Professional Diploma in Strategic Marketing from CIM | The Chartered Institute of Marketing.