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For over 35 years, Kip has led The Hollister Group as Owner & Founder with…
Articles by Kip
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Kip Hollister (she/her/hers) shared this38 years ago, I started this company on a belief that business could be built on real relationships rather than transactions. Today, I'm stepping into the next iteration of my leadership work focusing fully on my role as Owner & Founder, not away from Hollister, but more fully into the work I love most: executive team transformation, leadership development, individual and team coaching, and keynote speaking. Phoebe Goldsberry has stepped into the role of CEO, and I could not be prouder to see her carry this company forward with the same conviction it was built on.Kip Hollister (she/her/hers) shared thisWe are excited to share a new chapter for The Hollister Group. Phoebe Goldsberry has been named CEO. Allyson McCabe carries forward her role as President, and Kip Hollister (she/her/hers) continues as Owner & Founder. For nearly four decades, our work has been rooted in real relationships, and we look forward to continuing to support people, teams, and businesses as they grow. Read more on our website: https://lnkd.in/dPgmWHwB #PressRelease #StaffingAgency #Leadership #BostonBusiness
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Kip Hollister (she/her/hers) shared thisI always say that your energy walks into the room before you even open your mouth. The energy at the SCORE Mentors 2026 Massachusetts Women’s Summit was magnetic. It made it easy to share stories and lessons from the past four decades at The Hollister Group. One of the questions I received was about AI and where I believe it belongs in leadership. I value AI tremendously. We must lean in, learn, and recognize its potential, but it cannot replace the human need for genuine connection. Nor should we allow it to replace our authenticity, intuition, or energy. Leadership is about leverage. When used thoughtfully, AI can give us more time to lead from the front, strengthen relationships, and better serve our people. But the heart and soul of our organizations must remain human, and people's development must remain a priority. Thank you to SCORE Mentors, an incredible nonprofit that provides entrepreneurs with mentorship at no cost. I wish I had access to this kind of support when I began my journey at the ripe age of 26! I applaud your commitment to helping people grow into their most courageous selves. We are all worthy, and we each have gifts to share in the service of others. #Leadership #AIandLeadership #HumanConnection #WomenEntrepreneurs
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Kip Hollister (she/her/hers) shared thisThis week, I'm highlighting Socrates Rosenfeld, sharing his perspective on strong leadership. https://lnkd.in/e4Gxv4BV
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Kip Hollister (she/her/hers) shared thisHappy 31st Birthday, Chase. ❤️ Thirty-one years ago today, you came into my life. For 23 remarkable years, I had you here in the physical. And I have you still energetically, through your essence, your love, your light, and all you continue to teach me. Over these past eight years, I have realized that I would much rather celebrate the day you came into this world than dwell in sorrow on the day you left it. Perhaps that is one of your greatest gifts to me: moving from grief to gratitude. Not denying grief. Not “moving on.” But discovering that profound grief and profound gratitude can exist side by side. I love thinking of Mom with you now. A month before she took flight on May 12 at 94, she spoke profoundly to the five of us, her children, about grief and gratitude. Her passing is another tremendous loss for us all, and yet feeling her with you brings me such joy. In fact, just a week before she left, Mom suddenly pointed and said, “I see Chase right around the corner.” I will never forget it. And today, as I listen to Joni Mitchell sing "Both Sides Now," those words feel even more meaningful. The clouds and the sun. Grief and gratitude. Loss and love. Knowing and mystery. Losing you brought me to my knees, Chase. And somehow, it also woke me up. It taught me how easily we can become trapped in our thinking, believing our thoughts and identities are who we truly are. Underneath all that thinking is something deeper: Wisdom. Resilience. Love. When we become still enough to listen, something wiser can emerge. Maybe this is what I have come to understand: Grief says, “I miss you.” Gratitude says, “Thank God I had you. Thank God, I still have you.” Love says, “I still do.” Chase, you have taught me about impermanence, resilience, and the mystery of this life. You have taught me to loosen my grip on what I think I know, to “unknow my knowing” and trust the wisdom within. And most of all, you continue to remind me: Let Love Lead. ❤️ Tonight, we shall raise a glass of our favorite gimlet, the drink I turned you and Mamma on to and that you both loved, knowing you are with us. To life. To love. To becoming. Happy 31st Birthday, Chase. ❤️ https://lnkd.in/eAc_u88v
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Kip Hollister (she/her/hers) shared thisI’m thrilled to be one of the keynote speakers at the 2026 Women’s Business Summit on September 16th! It’s going to be a wonderful day bringing together women entrepreneurs, business leaders, and mentors for meaningful conversations, connection, and growth. I wanted to pass along the details in case you or someone in your network would like to join us!
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Kip Hollister (she/her/hers) shared thisAs I'm right in the middle of one of my Live Beyond Your Limits retreats, I'm filled with gratitude for this extraordinary group of women. It's amazing how quickly lives can begin to change when we create the space to slow down, challenge our limiting beliefs, and choose a new perspective. I am so honored to be doing this work and supporting them in this leadership journey. #WomeninLeadership #LeadershipDevelopment
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Kip Hollister (she/her/hers) shared thisWhat an incredible evening at the Pat Roche Hospice House in Hingham, surrounded by the beauty of the gardens and the even greater beauty of people whose hearts are dedicated to making a difference during life's most sacred moments. Having recently lost my mother-my soulmate-and witnessing firsthand how hospice allowed her to leave this world with grace, dignity, comfort, and without fear, I know how profoundly this work impacts not only the patients but also the families who walk alongside them. A heartfelt thank you to Renee McInnes, Michael Rogers, and the entire team at Croí Health for believing in this mission and stepping in to lead such an important cause. Each of us has the opportunity to contribute in our own way, and together we can make a meaningful difference in the lives of others. The impact of this work is immeasurable.
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Kip Hollister (she/her/hers) shared thisI'm excited to share my latest podcast conversation with the remarkable Susan MacKenty Brady, Founding CEO of the Simmons University Institute for Inclusive Leadership. Susan has long been a leader I admire-someone who truly leads from the inside out, bringing authenticity, courage, and heart to everything she does. In this episode, we explore what it means to practice intentional leadership, the power of self-awareness, and the ideas behind her new book, All the Difference. We recorded this conversation while walking in nature-a place that inspires reflection, clarity, and better leadership. I hope our discussion leaves you with fresh perspectives and practical insights for your own leadership journey. https://lnkd.in/eKJ9_xzXLeading from the Inside Out with Susan MacKenty Brady - The Hollister Group, Inc.Leading from the Inside Out with Susan MacKenty Brady - The Hollister Group, Inc.
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Kip Hollister (she/her/hers) shared thisThis is where it is at and we must invest in our humans to support them moving from fear to FLOW, yes yes yes! We are all conditioned by fear, scarcity and lack and thus must unlearn and re learn to be able to innovate.Kip Hollister (she/her/hers) shared thisThis week reinforced something I deeply believe. The future of work is not fundamentally a technology conversation. It is a human one. I had the privilege of moderating two sessions at the #HRWorldSummit in Porto 🇵🇹 on AI, leadership, and employee experience, and I left energized by the depth, honesty, and urgency of the conversations taking place among CHROs, researchers, academics, and business leaders from around the world. There were many memorable moments. Connecting with keynote speaker Stan Slap and hearing his reflections on leadership and human connection. Listening to conversations about moving people from fear to flow. Exploring whether AI is actually forcing us to redevelop some of our most important “caveman skills” - trust, adaptability, collaboration, emotional intelligence, and community. During our panel discussion I asked “What is the one leadership quality that will matter most in the age of AI?” The answers - human, empathy, and wisdom - which captured the spirit of the discussions. One insight that especially stayed with me came from Uzair Qadeer Qadeer, CHRO at the BBC, who described HR as “activators of human performance.” That framing perfectly captured the shift many of us are feeling. HR is no longer simply supporting transformation. We are helping shape it. And perhaps even more importantly, CHRO's are becoming architects of what work becomes next. Like Gaudí, whose work transformed complexity into something deeply human, enduring, and alive, HR leaders now have the opportunity to design organizations that are not only technologically advanced, but intentional, meaningful, and profoundly human centered. I’m incredibly grateful to the outstanding leaders I had the opportunity to moderate and learn alongside. AI Ready Workforce Skills and Capabilities Michelle Winestock (TP) Artem Ivanenko Prof. Dr. Anja Schmitz Navigating Employee Experience in the Age of AI Christine Kirbach Katalin Biro Teresa Coelho Inga Staniune Clémence Jacqueri It was also wonderful to share this amazing experience with Boston colleagues Siobhan McDonald from Mitsubishi Electric - Digital Solutions and HRLF (Human Resource Leadership Forum) colleague Violetta Drobot, MS in HRM and PM, SHRM-SCP. If this week reinforced anything for me, it is this. Organizations that will succeed in the age of AI will not simply be the fastest adopters of technology. They will be the ones designed with the deepest understanding of people and building workplace cultures that can "Find their Polar Bear!" Thank you Mark Agnew Keynote Speaker!
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Gillian O. and I was inspired by all of you. You are doing great things and there live events really matter so keep it up.
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Kip Hollister (she/her/hers) liked thisI am truly honored to have been appointed to serve on the Massachusetts Health Connector Board of Directors. This appointment represents an incredible opportunity to contribute to work that impacts individuals, families, employers, and communities across the Commonwealth. Throughout my career, I have remained committed to strengthening organizations, advancing equity, developing people, and creating opportunities for communities to thrive. I look forward to bringing that experience and perspective to the Board while learning from and serving alongside an accomplished group of leaders. I am grateful for the opportunity to serve the Commonwealth of Massachusetts in this capacity and excited about the work ahead. Service. Leadership. Impact. #MassachusettsHealthConnector #Leadership #BoardService #PublicService #HealthEquity #CommunityImpact #WomenInLeadershipKip Hollister (she/her/hers) liked thisThe Massachusetts Health Connector is pleased to welcome Lauretta Siggers-Benton, MBA, CHRM, to our Board of Directors, where she will serve as a vital voice representing small businesses across the Commonwealth. Ms. Siggers-Benton brings decades of leadership in the non-profit and public sectors, along with firsthand experience as a small business owner advising mission-driven organizations. Her extensive background across human resources, employee benefits, and community engagement makes her perspective an indispensable asset to our leadership team. "Lauretta has spent her career helping organizations and communities grow stronger, and she brings important experience as a small business owner and leader," said Governor Maura Healey. "I know she will be a strong voice for small businesses and the people who rely on the Health Connector." "Ms. Siggers-Benton’s extensive business expertise and experience serving as a leader in her community will be invaluable to us as we work to position the Health Connector to best serve our residents, small businesses, and local economy," added Health Connector Executive Director Audrey Morse Gasteier. Effective immediately, Ms. Siggers-Benton will participate in upcoming Board meetings to help guide our continued mission of delivering high-quality, affordable health and dental coverage to Massachusetts residents and employers. Please join us in welcoming Lauretta to the Health Connector Board! 🔗 Read the full announcement: https://lnkd.in/gw2t2dSs #MAHealthConnector #HealthConnectorForBusiness #BoardOfDirectors #SmallBusinessMA #Massachusetts #Leadership
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Kip Hollister (she/her/hers) liked thisKip Hollister (she/her/hers) liked thisA new CEO. The same people-first commitment. Phoebe Goldsberry has stepped in as CEO of The Hollister Group after 11 years with the company - bringing forward the relationship-led approach Kip Hollister (she/her/hers) established 38 years ago. As Phoebe writes, “we are people first, and we always will be.” From finding the right talent to helping organizations grow their leaders and teams, The Hollister Group’s focus remains on relationships built to last. Read Phoebe’s full letter and learn what this next chapter means: https://lnkd.in/dkPn4cKH
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Kip Hollister (she/her/hers) liked thisKip Hollister (she/her/hers) liked thisHUB International is a place where the opportunities show up as fast as I'm ready for them, whether that's a new challenge, a bigger scope or a chance to lead. That's not an accident. When ambition is built into how we grow our own people, clients get advisors who've never stopped raising their own bar. #ForEveryAmbition #LifeAtHUB HUB International
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Kip Hollister (she/her/hers) liked thisKip Hollister (she/her/hers) liked thisIt’s true that frailty looks different for everyone. How early it's caught can change a patient's trajectory. Frailty can appear in everyday tasks like walking speed and grip strength a full decade before decline. The referenced clinical trial found that 20 minutes of daily strength and balance exercise, paired with more protein, improved grip strength and bone density for many in three months. That's why Croí Health offers classes promoting movement to our community. Building strength and balance can go a long way in your aging journey. Visit croihealth.org to learn more. https://lnkd.in/gMa2xhsPFrailty Is More Than Just Weakness. Here's What to KnowFrailty Is More Than Just Weakness. Here's What to Know
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Kip Hollister (she/her/hers) liked thisKip Hollister (she/her/hers) liked thisYesterday, I had so much fun with Eudad Gonzalez sharing our experiences of leadership with this year’s ELDS AGC cohort. The energy and commitment was contagious - industry leaders excited to make a positive impact in the lives of their teams, clients, partners and co-workers, hone their skills, and grow. Thank you, Briana Whynott and Emily Fletcher for chairing this cohort, to Associated General Contractors of Massachusetts (AGC MA) and Eudad for this opportunity!
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Kip Hollister (she/her/hers) liked thisKip Hollister (she/her/hers) liked thisWe often talk about spring and summer as the busiest months for housing, but the data shows that the final four months of the year continue to account for a significant share of annual home sales. The share of existing-home sales taking place between September and December has increased every year since 2023, and the 2026 forecast puts that figure at 34.1%. That means more than one-third of annual existing-home sales are expected to happen in the final four months of the year. It is worth keeping that in perspective when looking at the housing market as a whole. Seasonality matters, but there is still meaningful activity happening well beyond the traditional peak selling season. radius financial group inc. | #radiusgrp #MortgageIndustry
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Kip Hollister (she/her/hers) liked thisKip Hollister (she/her/hers) liked thisWe had a helluva day at the 2026 Gallagher H&B Summit! Thank you so much to our wonderful clients for their perspective and engagement (who says you guys have the attention span of a goldfish?!). Surprise of the day? The #MarkCuban theme…guy was everywhere! The other major theme was around connectivity. We talked about the future of leadership, humanistic AI, telling a story through data & analytics, communications strategy, pharmacy trends and financial well-being (microbursts, ftw). Thanks to our speakers who hosted an excellent panel: Jenna Arruda, PHR, SHRM-CP, Crystal N. McDermott, CEBS, Caryn Goulet, SCP, SPHR® Shout-out to the sponsors who supported the program: Sun Life, Avante, Innovu, EmpiRx Health, Transamerica (NortonLifeLock for HH). Kevin Gazda, Madison Braman, Danielle Matthew- such a fantastic Ops team. Your hard work made the day look easy.
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Kip Hollister (she/her/hers) liked thisKip Hollister (she/her/hers) liked thisWayside has been named a 2026 Top 100 Women-led business by The Women’s Edge. It is such an honor to celebrate this award with my incredible leadership team as well as inspiring and talented female colleagues. Thank you The Women's Edge for the recognition.
Experience & Education
Licenses & Certifications
Volunteer Experience
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Member
WBL (Women Business Leaders of the US Health Care Industry Foundation)
- Present 4 years 4 months
Honors & Awards
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2023 Best CEO for Women - #41
Comparably, Inc.
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2023 Largest Temporary Placement Firms in Massachusetts - #8
Boston Business Journal
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2022 Best CEO - #96
Comparably, Inc.
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2022 Best CEO for Diversity - #98
Comparably, Inc.
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2022 Best CEO for Women - #20
Comparably, Inc.
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2022 Largest Executive Search Firms in Massachusetts - #22
Boston Business Journal
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2022 Largest Women-Owned Businesses in Massachusetts - #11
Boston Business Journal
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2022 Top 100 Women Led Businesses - #78
The Women's Edge & Globe Magazine
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2022 Top Places to Work - Small Employers - #12
The Boston Globe
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2021 Best CEO - #15
Comparably, Inc.
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2021 Best CEO for Women - #46
Comparably, Inc.
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2021 Top 100 Women-Led Businesses - #82
Commonwealth Institute & Globe Magazine
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2020 Best Places to Work - #12
Boston Business Journal
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2018 $25 to $100 Million Annual Revenue Category Award
Enterprising Women
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2018 Academy of Women Achievers Award
YW Boston
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2018 Best Places to Work - Small Company - #19
Boston Business Journal
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2017 Top 100 Women Led Businesses - #85
Commonwealth Institute & Globe Magazine
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2017 Best Places to Work - Small Company - #7
Boston Business Journal
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2017 Largest Temp Placement Firms in Massachusetts - #13
Boston Business Journal
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2017 Top Places to Work - Small Company - #17
Boston Globe
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2016 Best Places to Work - Small Company #15
Boston Business Journal
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2016 Brava Award Honoring Top Female CEOs
Smart CEOs
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2016 Largest Minority & Women-Owned Businesses in Massachusetts - #11
Boston Business Journal
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2016 Largest Temp Placement Firms in Massachusetts Award - #13
Boston Business Journal
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2016 Top 100 Women Led Businesses Award - #91
Commonwealth Institute & Globe Magazine
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2015 Largest Temp Placement Firms in Massachusetts Award - #12
Boston Business Journal
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2015 Top Women Led Businesses Award - #76
Commonwealth Institute & Globe Magazine
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2014 Top Temporary Placement Firms in Massachusetts Award - #14
Boston Business Journal
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2014 Top Women Led Businesses Award - #27
Commonwealth Institute & Globe Magazine
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2014 Women Up Awards
Boston Business Journal Local Women of Influence
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2013 Top 100 Women We Admire Award
Ad Club of Greater Boston
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2013 Top 100 Women-Led Businesses Award - #40
Commonwealth Institute & Globe Magazine
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2013 Women Who Live United Award
United Way of MA Bay & Merrimack Valley
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2012 Employer of the Year
YMCA Training Inc.
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2012 Entrepreneur of the Year Award in Service from New England
Ernst & Young
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2012 Top 100 Women Led Businesses Award
Boston Business Journal
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2011 Small Business of the Year Award
Greater Boston Chamber of Commerece
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2011 Top 100 Women Led Businesses Award
Boston Business Journal
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2010 Top 100 Women Led Businesses Award
Boston Business Journal
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2008 Enterprise Woman of the Year Award
Enterprising Women
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2008 Pinnacle Award for Entrepreneurship
Boston Chamber of Commerce
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2006 Stevie Award
The Stevies for Women in Business
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