Discover Willis Towers Watsons Keisha Olingers inspiring story

Discover Willis Towers Watson's Keisha Olinger's inspiring story

 November 22, 2021

Meet Willis Towers Watson Managing Director, Keisha Olinger.

Keisha shares how she her career has grown, how she has amplified her voice, and how she has worked to seize key opportunities as a Black woman. 

Discover Keisha’s unique advice and inspiring story.


Tell us about your career journey at Willis Towers Watson

I began my career with Willis Towers Watson in 2005 as a communications associate consultant in the Atlanta office. I’m proud to say that ever since I joined the company, I’ve had the opportunity to help diverse, complex, global organizations – including ours – manage change through mergers and acquisitions as well as significant benefit and technology advancements.

What are you responsible for at Willis Towers Watson?

Currently, I’m the Client Management Leader for Georgia, Alabama and Tennessee as well as the Client Relationship Director (CRD) for North America. My role as a CRD is to manage the totality of the Willis Towers Watson relationship with our largest, most complex clients. I partner with external teams across Human Resources, Finance and Risk to evaluate how we can support their business strategy. I’m also responsible for assembling the best team of colleagues to find and execute the appropriate solutions for our customers’ unique objectives.

Additionally, as Client Management Leader, I lead the team of CRDs in the region to partner with other business areas to help build and nurture an inclusive and engaging community for our colleagues and clients.

Explain your experience becoming a Willis Towers Watson managing director

Willis Towers Watson - supporting female Black women employees

When I first joined Willis Towers Watson, I didn’t envisage becoming a managing director. I was a divorced, single mother of a then four-year-old daughter and six-year-old son. My children were used to me having a job where I worked long hours, but I was looking for a career that made me feel fulfilled and had a sense of purpose. I found that at Willis Towers Watson. Here, I felt empowered and confident to say ‘yes’ to challenging projects. I also found a community of smart, collaborative colleagues who said ‘yes’ to giving me new and expanded responsibilities. My first manager and mentor, Elizabeth Byerly, would often say ‘get comfortable with the uncomfortable’. That advice has stayed with me throughout my career; from feeling comfortable in managing scopes and budgets when I was new to sales, to being the only woman or Black colleague in a client meeting. This saying ‘yes’ and ‘getting comfortable with the uncomfortable’ mindset – and always looking to work with a sense of purpose – helped me chart my career path.

Why do you think it's key to have diverse leaders within an organization?

It is a fact that diverse teams bring different perspectives, which enhances creativity and problem solving. This is particularly important at a leadership level, as it helps strengthen our company’s Inclusion & Diversity (I&D) efforts and our clients’ initiatives in creating diverse and inclusive workplaces.

How do you see I&D come to life via your Willis Towers Watson role?

I’m glad to see how discussions around diversity, equality and inclusion have evolved throughout my 16-year journey at Willis Towers Watson. Personally, I am committed to ensure our awareness conversations around I&D continue to develop into meaningful actions.

I’ve also been an active member of our company’s colleague led I&D initiatives. I was an early supporter of Willis Towers Watson’s Gender Equality Network and part of the Multicultural Inclusion Network and Black Colleague Connections group. I’m especially proud of the COBALT (Creating Opportunities for Black and LatinX Talent) program that we launched in 2020 in four cities in North America. This program’s goal is to improve and advance representation and integration of Black, African American, and Latinx colleagues at all levels of the company through innovative programs – from expanding the list of targeted universities for early careers recruiting to sponsoring mentoring programs for existing colleagues.

What's your advice for someone part of ‘the first, the only, or one of the few’?

It can be hard, challenging and an immense responsibility to be one of ‘the first, the only, or one of the few’. My number one piece of advice is to say ‘yes’ to opportunities and to allies who offer their support and mentorship. I often ask myself, ‘why not me?’ and ‘why not now?’ when facing an opportunity. I also ask the same questions to mentors whose advice and counsel I trust. For example, when I first thought about advancing my career and becoming a managing director, I asked myself and a few colleagues ‘why not me?’ and ‘why not now?’. After working on strengthening my skillset and capabilities, I said ‘yes’ to raising my hand and my voice for career progression to managing director, even when it meant being among ‘the first, the only or one of the few’ Black women to do so.

What advice do you have for addressing underrepresentation of women and women of color in senior management?

I encourage every leader to look around and recognize the pockets of ‘the first, the only or one of the few’ within their organizations. Listen to them. Sponsor them. Promote them.

I’m blessed to have a varied and interesting career at Willis Towers Watson, helping the world’s most complex organizations solve some of their biggest people and risk issues, working alongside brilliant colleagues. This is a company where we’re encouraged to grow and to challenge ourselves and the status quo. I can’t wait for all of the future women, women of color and Black women who will become managing directors in the future.


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