Jessica DeOliveira SUn

Jessica DeOliveira Sun is a Managing Director at Raines International, leading Client Delivery & Commercial Excellence. She is responsible for the firm’s integrated approach to executive search delivery, commercial strategy, marketing, and technology, with a mandate to accelerate growth and elevate client experience. Her remit includes advancing go-to-market strategy, strengthening commercial effectiveness, and leading Raines’ AI and technology transformation—deploying tools that enhance execution, improve productivity, and expand access to market intelligence. 

In close partnership with the CEO and Corporate Leadership Team, Jessica translates strategy into a coordinated operating model and leads the evolution of the firm’s executive search delivery framework. She leverages deep institutional knowledge and practitioner insight to establish the systems, processes, tools, and infrastructure that enable pace, responsiveness, consistency, and data-driven execution across engagements. 

Jessica joined Raines in 2014 as a researcher and progressed through every role as an executive search practitioner, culminating as Managing Director within the firm’s Consumer and Operational Excellence practices. Working with clients across Private Equity and Fortune 500 environments, she developed a grounded understanding of what drives successful executive search—from client engagement and candidate experience to the operational rigor required to deliver consistent outcomes. 

That experience now directly informs how she designs and implements the processes and infrastructure that underpin delivery and growth. This combination of hands-on executive search experience and firm-level leadership enables Raines to operate with greater cohesion, sharper market positioning, and a more deliberate, data-informed approach to growth.