Scaling empathy moments that matter: Building inclusive cultures from day one with Brooke Sullivan
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What happens when you take fifteen years of startup chaos, a front row seat to the exact moment culture either takes root or falls apart, and a leader who gets excited about the hard conversations most people run from? You get this conversation with Brooke Sullivan, Director of People and Talent at Banyan Software, and a leader building belonging inside fast-moving companies.
Brooke has spent her career inside software startups, building people functions from zero, from the "we do not even have an org chart yet" phase, and turning that scrappiness into something real. She has a gift for what she calls scaling moments, that critical twenty-to-one-hundred-person inflection point where inclusive culture either becomes the foundation or something you wish you had built.
In this episode, Brooke shares the practices and small everyday moments that create workplace belonging long before a handbook ever could. She walks us through her Exercising Empathy programming, the one-on-one design choice that changed how leaders showed up for their teams, and the moment she realized the language a company uses for its people reveals everything.
This is a conversation about authentic leadership, human-centered innovation, and what it takes to foster a sense of belonging at work when speed and scale are pulling in opposite directions. Brooke gives listeners practical language for belonging, grounded in fifteen years of building people experience.
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Must-hear insights & key moments
Why the twenty-to-one-hundred-person window is the make-or-break moment for inclusive culture in scaling startups
The Exercising Empathy programming Brooke built to give teams permission to talk about the hard things at work
A one-on-one design choice, a green or red box at the top of the doc, that lets leaders see what is distracting their people without forcing the conversation
The Bechdel test for meetings and the question Brooke uses to surface who is missing from the room
How the words a company uses for its people reveal whether belonging is real or performative
Why friendship at work is one of the strongest signals of workplace belonging
The story behind Brooke's name and what it taught her about honoring the people who shape us
Brooke’s standout quotes:
"There's a human sitting across from you, whether it's virtual or in person, and sometimes you're the first person that listened to them all day."
"If someone had a friend at work, they felt a deeper sense of belonging."
"You are gifted to care for these people."
"We talk about hard things here. We hold space for each other here."
"If you don't have people, you have nothing."
"My belonging comes from myself until it comes from that organization or that community."
"I know I belong when someone shares something really personal with me."
Why this episode matters
Building a sense of belonging in fast-scaling companies is not a side project. It is the work. Brooke shows leaders, HR practitioners, and founders how strategic inclusion lives in the smallest design choices: the language we use, the questions we ask, the connection moments we engineer on purpose. This episode reframes belonging vs inclusion in plain terms and gives listeners a working vocabulary for creating belonging at work inside teams that are moving fast and figuring it out in real time.
Who should listen
People leaders, founders, HR and talent professionals, DEI practitioners, and managers building inclusive culture inside startups, scaleups, and hybrid or remote teams. This episode is for anyone scaling a team through that twenty-to-one-hundred-person window, anyone creating belonging at work without a playbook, and anyone who wants stronger language to talk about belonging in the workplace, authentic leadership, and people experience in ways their teams can feel.