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A 12-month milestone conversation on leadership brands, social presence, and executive readiness
The twelfth installment of the HR Gamechangers series pulled back the curtain on what it really takes to rise into a CHRO seat. Moderator Janelle Henry was joined by three seasoned people leaders—Allyson Carr (Cybereason), Vanesa Cotlar (PolicyMe), and Jessica Winder (Colab)—for a fast-paced hour of candid stories and practical frameworks.
This milestone episode surfaced a clear throughline: climbing into the top HR role is as much about business acumen and influence as it is about HR expertise. From building a leadership brand to earning a strategic seat, and from executive positioning to leading with humanity, here are the core themes that emerged and the moments that lit up the chat.
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Speakers
Janelle Henry: Talent and Brand at Stripe, Advisor & Former VP of People at Rad AI & GoProfiles customer (moderator)
Allyson Carr: Chief People Officer at Cybereason
Vanesa Cotlar: VP of People & Culture at PolicyMe
Jessica Winder: SVP of People at Colab
Key Takeaways:
A distinct leadership brand rooted in authenticity: Clearly signal who you are as a leader, what you stand for, and how you add value. Authenticity builds trust across the organization.
Business fluency deep enough to debate product, revenue, and cost models: Understand your company’s financial drivers, competitive landscape, and KPIs to contribute at the highest strategic level.
A curated social presence that educates, engages, and attracts talent: Share insights and showcase culture to position yourself as a thought leader and talent magnet.
An ever-expanding community of peers who sharpen your perspective: Build a strong network of leaders to exchange ideas, solve challenges, and stay adaptable.
Relentless executive positioning through cross-functional credibility: Earn influence by partnering beyond HR, sharing data-driven insights, and solving business challenges.
Defining and Owning Your Leadership Brand
The conversation opened with an exploration of leadership brands—how HR leaders present themselves, what they stand for, and the perceptions they shape inside and outside their organizations.
For Vanesa Cotlar, that brand centers on translating strategy into people impact. She’s intentional about framing herself as a business leader who happens to specialize in people.
“I always say I’m a business leader first. HR used to be seen as task execution and admin. That’s a very low-value way of looking at people and culture.”
—Vanesa Cotlar, VP of People & Culture at PolicyMe
Moderator Janelle Henry echoed this sentiment, underscoring that in the CHRO seat, virtually every company challenge is, at its core, a people challenge.
“Everything eventually comes back to people. From compensation and performance to how people are feeling and their tenure with the company, there really aren’t challenges that don’t touch the CHRO world.”
—Janelle Henry, Talent and Brand at Stripe, Advisor & Former VP of People at Rad AI
This theme set the tone: your leadership brand should signal that you’re a strategic partner, not a back-office function.
Getting Into “The Room Where It Happens”
Once your leadership brand is clear, the next hurdle is ensuring you have influence where the big decisions are made. The panelists agreed: earning and keeping a strategic seat requires proactive integration into business conversations.
Allyson Carr built her influence on financial fluency and cross-functional trust, challenging HR leaders to contribute more than just an “HR update” in executive forums.
“One: get yourself in the conversation and in the deck. Two: when you’re there, actively listen, participate, ask questions, be a business partner, not just the ‘HR slide.’ The more you can get in the room and share data, share metrics, and ask about other functions, the more you evolve the perception that HR truly understands the business.”
—Allyson Carr, Chief People Officer at Cybereason
Jessica Winder distilled it down to action: you can’t influence what you don’t understand.
“Go join other people’s meetings—you can’t influence what you don’t understand. If you are in HR and you’re given an opportunity to go beyond HR and into the business, take it—take it all day long.”
—Jessica Winder, SVP of People at Colab
Vanesa Cotlar emphasized the importance of relationship-building with leaders across the organization from day one.
“I meet with all the functional leaders, I know how their teams operate and where things could change. I position myself as part of that conversation from day one.”
—Vanesa Cotlar, VP of People & Culture at PolicyMe
The clear takeaway: your seat at the table isn’t granted. It’s earned through presence, preparation, and perspective.
Executive Positioning: Steps Toward the CHRO Seat
The conversation then shifted from influence to readiness. How do you position yourself as the obvious choice when the CHRO role opens up?
For Allyson Carr, it starts with deep business understanding.
“You have to truly understand your business; you have to understand how your company makes money. Know your financials inside and out, the KPIs, and bring data into every conversation.”
—Allyson Carr, Chief People Officer at Cybereason
Jessica Winder noted that senior hiring can be a powerful networking and influence tool. By playing a hands-on role in recruiting executives, she forged early partnerships with CFOs and COOs—relationships that later opened strategic doors.
“Being very strategic about the people that you’re bringing in and making sure that you are already partners with them as soon as they start goes so far.”
—Jessica Winder, SVP of People at Colab
From the panelists’ collective experience, a few practical moves stood out for mid-career professionals:
Expand beyond HR – Take opportunities to step into operations or cross-functional projects.
Master comp and rewards – Compensation literacy is a fast credibility booster.
Invite non-HR leaders into your world – Opening HR meetings builds transparency and allies.
Listen first, talk second – Strategic silence can heighten perceived insight.
Each of these moves adds a layer to your executive profile, signaling that you’re not just an HR expert, you’re a business leader ready to take the helm.
The Human Side of Leadership
The episode closed on a more personal note: memorable feedback and moments that shaped the panelists’ leadership styles.
Allyson Carr spoke about the power of “watching and listening” to absorb boardroom dynamics before speaking. Vanesa Cotlar reminded leaders that audience awareness should guide every interaction, both in person and online.
It was a fitting end to a conversation that balanced strategic ambition with authenticity. The panelists made clear: leadership is a human endeavor first.
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