Join us for our installment of the Pacesetters Doing Business series featuring Mass General Brigham on August 7, 2025.
08/07/2025
1:00pm - 2:00pm
Virtual
The BIMA Summer Sizzler is a chance to network with your digital media industry peers from the agency, publisher, and adtech community!
08/14/2025
6:00pm - 9:00pm
Fenway Park
Join Boston’s leading educators and industry experts to explore career-aligned high school programs, in-demand workplace skills, and innovative school partnerships driving student success
07/17/2025
9:00am - 11:00am
Omni Boston Hotel Seaport
This program is in redevelopment. Click this page for DEI resources.
Our Women’s Leadership Program enables you to take your leadership to the next level by arming you with the most in-demand leadership toolkit.
Our Boston’s Future Leaders (BFL) program provides emerging leaders with a socially conscious and civically engaged leadership toolkit, as well as the opportunity to apply their knowledge through experiential assignments.
In this highly interactive workshop with Strategic Career & Leadership Coach Carole-Ann Penney, you’ll define your professional identity and develop strategies to confidently navigate workplace dynamics.
City Awake empowers young professionals in a variety of ways that encourages these rising leaders to stay invested in the region’s future success.
We are developing an ecosystem of corporations and partners with the influence and buying power to transform economic inclusion for minority business enterprises (MBEs).
Small businesses are the backbone of the Boston economy. Learn more about the resources available through the Chamber.
BIMA (the Boston Interactive Media Association) serves a vibrant community of like-minded professionals from agencies, brands, publishers, and ad-tech companies with business interests in the New England market.
For over 30 years, the Chamber’s Women’s Network has connected female professionals of all background and career levels. Today, our Women’s Network is the largest in New England, strengthening the professional networks of women each year.
The Massachusetts Apprentice Network convenes employers, training providers, and talent sources interested in developing and implementing apprenticeship programs in occupations across industries and statewide in fields such as tech, advanced manufacturing, healthcare, financial services, and more.
Explore our mission and values to better understand how we are leading the business community forward.
Our member directory is your resource to discover, connect, and engage with Boston’s businesses from every industry and sector.
On Tuesday, March 29, the Women’s Network held its first in-person event of 2022. The Women’s Network Breakfast featuring Karen Kaplan of Hill Holliday was a live discussion with moderator Susan Penta, Co-Founder and Managing Partner at MIDIOR Consulting and the new Chair of the Women’s Network Advisory Board.
Karen Kaplan is Chair & CEO of Hill Holliday, one of Boston’s biggest ad agencies. During the conversation, Karen shared her unique journey from receptionist to CEO, and how her fresh perspective on business, her determination, and drive developed her into a key player in the agency’s significant growth as a national powerhouse.
Karen also shared her insights on seizing opportunities, the importance of championing women, leading during the global pandemic, and the secrets to trailblazing as one of the few female agency chairs in the country. Here are the event’s key takeaways:
Karen shared how one of Hill Holliday’s founders, Jack Connors, said something to her when she got the receptionist role that really changed her life. He said “congratulations, Karen, you are now the face and the voice of Hill Holliday.” This made Karen realize that it was not just some job, it was important. “The face and voice of Hill Holliday – that sounds like something the CEO should be responsible for. So, I considered myself the CEO of the receptionist desk.”
Karen emphasized that she was the last person you would think would spend their entire career in one place. “That was not the plan. Never in my wildest dreams,” she said. She was always really focused on the job she had, and for her, Hill Holliday was a place where she would be presented with an opportunity that she believed was beyond her capability at the time, and Jack Connors would show her that he believed in her, which led her to believe in herself. And that happened to her over and over again throughout her career there.
“If you are in an environment and you are challenged, and someone believes in you[…] it forces you to get really good at kind of parachuting into a category, figuring out what is important, versus what is not so important, sifting through a lot of data, and figuring out where the insights are, and figuring out how to add value without getting caught in the weeds.”
Karen looked at those words every day for two years since the start of the pandemic. She wrote an email to the agency every day for 100 days, and told her team to put two words at the end of every sentence – for now. “We’re still in the ‘for now’ period. And we still need to meet people where they are,” Karen emphasized.
Building off of the last takeaway – Karen has a “wherever, however policy.” She talked about how, in the current climate, it’s important to meet people where they are, and understand there’s been a lot of trauma over the past two years. Karen expressed having social jetlag, which there appears to be a lot of nowadays. People have to do things at their own pace. Some people are energized by being in the office, and some are energized by being at home. We’re not all going to be at the same place and same time ever again, and that’s okay.
Karen reminded us that as long as a company values ideas, great ideas can help level the playing field.
Even if you don’t know the secret handshake, ideas can serve as currency. “Women and historically excluded groups are better at thinking outside of the box because we have never been allowed inside the box, and most of us don’t even know where the box is.”
“Depending on what kind of business you run, you are very vulnerable when you put your idea out there. Ideas are the easiest things to kill, they are such subjective things,” said Karen. She worried that when Hill Holliday shifted to a remote model, they would not be able to function as successfully. Believing the creative process is easier in person, she thinks they suffered a little bit, but they managed to figure it out. One key to their success? A strong culture.
They also continued to work toward getting to the root of what their clients were all about and emphasizing the aspects of humanity in order to connect clients with their consumers.
“Every company has a soul. It’s not enough to just be in the business of doing business, it is our job to uncover what that is, separate out everything they sell, and determine what is the soul? Making a human connection as opposed to just talking to somebody. For a company to be able to connect with consumers on a higher-order, values kind of basis – that is the goal.”
In Karen’s opinion, that is what the best and highest use of an agency is, and is what Hill Holliday has always been good at.
Popular Resources