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Meet Wendy Karlyn of Rightpoint

Today we’d like to introduce you to Wendy Karlyn.

Thanks for sharing your story with us Wendy. So, let’s start at the beginning and we can move on from there.
When I started my career as an advertising specialist for a large software company, I noticed that the people from our advertising and marketing agencies always seemed to be having fun. The agency life seemed to be calling me, so soon thereafter, I landed my first job at a newly-formed digital agency called Strategic Interactive Group, which then became Digitas. It didn’t take long for me to realize that my instinct about agency life was right. I was Cinderella and the slipper fit!

My first four years were spent traveling back and forth from Boston to Detroit to work on the ground at General Motors. It was the late 90’s, and I was part of the team that created websites for General Motors’ online brands for the first time! Although this experience was intense, it proved to be an incredible training ground for managing clients, working with diverse teams and learning a lot about myself along the way.

In 2002, I jumped at the opportunity to join a few colleagues in opening a Digitas Chicago office. While building our client base was exciting, I learned that you can’t simply pack up a company culture and move it to a new city. This aspect of an expansion requires a delicate balance between integrating the shared values of the broader corporate culture while respecting the unique aspects of the region (knowledge I would later leverage in the business and cultural transition from Agency Oasis to Rightpoint, after last year’s acquisition).

After having our first child, my husband and I felt our Boston roots pulling us back home and in 2007 we returned. After more than a decade at Digitas, I decided to start a new adventure in a global leadership role at Sapient, in the Boston office, which was evolving into a digital agency. I traveled to Sapient offices all over the country, including India. This experience helped me to grow as a leader — learning how to drive cultural change and modify my style and approach to be successful.

After working in the big agency world, I decided to delve into my entrepreneurial side and joined Agency Oasis, a smaller digital agency that was experiencing rapid growth. Agency Oasis became Rightpoint in 2016, and I now work among Rightpoint’s local and national leadership team to drive the strategy and vision for our growth. I lead our business in the Northeast and I am also responsible for agency integration as part of Rightpoint’s national growth strategy, which includes acquisitions and capabilities expansion.

Here are a few of things that I’ve learned over the course of my career: 1) Be your authentic self and find the right work culture that will help you thrive. 2) Be flexible. In this business, you will win pitches and lose important clients. You will recruit great talent and watch star employees leave in search of new pursuits. Staying steady through change will help balance the ups and downs and is critical to surviving in nearly any business or career. I like to call this “embracing the gray.” 3) Passion wins. Being passionate about ideas, people and great work is contagious, so do what you love and share it with everyone around you. 4) Be kind. Start by giving people the benefit of the doubt, it goes a long way. 5) Own your mistakes. If you screw something up, tell your client or manager the truth and how you are going to fix it. Doing the right thing always works. 6) Be accountable and share credit. When things are working and achievements are made, share the glory and the credit. When something goes wrong, share responsibility – don’t pass the buck.

Great, so let’s dig a little deeper into the story – has it been an easy path overall and if not, what were the challenges you’ve had to overcome?
It has definitely not been smooth – but is any transition? Going from being a do-er to being a leader in the room is a process in building trust, credibility and confidence. To do this successfully has required learning to work with different leadership styles while also carving out my own. Growing as a professional has also entailed driving significant change in an organization, giving constructive feedback, handling criticism and making difficult decisions. The confidence and conviction that I have gained throughout this process have guided me throughout my career and led me to become a trusted leader at Rightpoint.

When a big change comes along, like a corporate acquisition, it’s all hands on deck to make the transition as smooth and seamless as possible. When we went through the acquisition process with Rightpoint, I worked with our Boston team to ensure that the dedication and innovation that built Agency Oasis was integrated into Rightpoint. For example, Rightpoint had been working with the Harvard Kennedy School of Government to rebuild their digital workspace, which had not previously been an area of focus. Becoming Rightpoint has expanded our offering in new and exciting areas and positioned us to win new clients and expand our Boston presence.

Alright – so let’s talk business. Tell us about Rightpoint – what should we know?
Rightpoint is an independent customer experience agency with technology at our core. Located in the heart of Downtown Crossing, Rightpoint’s Boston office serves as the hub for our business in the Northeast region. With 350 employees across eight U.S. offices, we create seamless digital experiences driven by insight, strategy, technology and design to evolve the way our clients do business.

We are fortunate to work with global and national marquee brands such Walgreens, Johnson Controls and Aon as well as Boston-based organizations including the Boston Red Sox and Boston Children’s Hospital. Driven by passion and rooted in our ability to connect the dots across every facet of a business, our customer experience solutions tie together content, commerce, website, managed services, CRM, BI, intranets, cloud and IoT. Our design and development experts get to the heart of our clients’ missions, and use those insights to deliver the best experience for their customers.

As the largest independent agency in the digital space, Rightpoint has the flexibility to push client visions forward, keenly focused on time, budget and excellence at every step. Our philosophy of shared responsibility provides team members with the tools, direction and creative freedom they need in order to chart the best path to success for every client engagement. These principles have become a competitive weapon in finding and retaining the best people in the industry.

Is there a characteristic or quality that you feel is essential to success?
I am amazed and inspired by the work and dedication of my fellow Rightpoint leadership team. I am part of a culture that encourages employees to work freely, think openly and create from within. This intrapreneurial culture combined with the unique work that we do has provided me with opportunities to take on new challenges and help to advance my role as a leader. Whether we are preparing for a new client pitch or deep into a complex engagement, nothing brings me greater pride and satisfaction than seeing the magic that happens when a team of diverse thinkers and talent come together to achieve our common goal. Rightpoint’s collaborative, “achieve excellence” attitude is pervasive in our culture and inspires me every day.

I will never forget the three amazing women who ran the marketing team at my first job. Together, they guided and encouraged me, gave me responsibility and taught me a ton about the business. At every critical stage of my career since then, I have had countless people who have impacted my career – mentors who coached me, teammates who inspired me, managers who advocated for me and clients who motivated me. Of course, my incredible family and friends have also cheered me on along the way, but my biggest supporters are my husband, Matt and my two sons, Evan and Max who have always encouraged me to go for it no matter what.

Contact Info:

  • Address: 101 Arch Street
  • Website:
  • Phone: 617-848-5435
  • Email:

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