We work with executive teams at the exact moments that decide whether a strategy holds
The specific transitions — a new CEO, a merger, a board-mandated reset, growth that's stalled — where alignment either holds or quietly breaks.
The October Group works with executive teams at the exact moment it matters most — a new CEO stepping into a role, a company navigating a merger or acquisition, a board demanding a strategic reset, growth that's stalled even though everyone's working harder than ever. We're not a general leadership development firm. We work with leaders during the specific transitions where alignment either holds or quietly breaks, and where the difference shows up fast, in results, not just in how the team feels.
If you've just taken over a leadership team, closed a deal, or watched growth stall even though everyone's working harder — you're who this page is for.
Dr. Philipia Hillman
Founder & CEO, The October Group
Philipia has spent more than 25 years inside the moments that actually test a leadership team — government, academia, and private consulting each put pressure on leaders in a different way, and she's led through all three. That range is why she can walk into a boardroom mid-transition and know within the first conversation whether a team is genuinely aligned or just agreeing out loud.
She holds a BA in journalism from Howard University and a PhD in sociology from American University, where she also served as an adjunct professor at both. She's certified in coaching through George Mason University, organizational development through Georgetown University, and in Appreciative Inquiry, Emotional Intelligence, and facilitation.
Outside the work, she's known for bringing real candor along with real warmth into a room, not one at the expense of the other. She lives in DC, volunteers on several boards, and spends her downtime on good meals, good conversation, and traveling with family and friends.
Four things that only work when they're pulling in the same direction, especially under pressure.
Develop Leadership
New CEOs, founders scaling past their comfort zone, and leaders inheriting a team they didn't build all face the same test: can they lead with clarity before the team decides for them whether they're credible. We help leaders pass that test in the first 90 days, not figure it out a year in.
Articulate Strategy
After a merger, a board reset, or a stalled growth plateau, most leadership teams can recite the strategy in a meeting and still walk out with five different interpretations of what it means. We turn that strategy into decisions your team can actually make on their own, without checking with you first.
Cultivate Culture
Culture isn't what's written on the wall — it's what happens when your best people are deciding whether to stay quiet or push back. We diagnose the real culture underneath the one leadership thinks it has, especially in the months after a major transition, when that gap is widest and most expensive.
Inspire Growth
Growth stalls for a specific reason: strategy and culture stop pulling in the same direction, usually right when the pressure is highest — a leadership change, an acquisition, a board demanding faster results. We help you close that gap before it costs you a year.
• Our Why
We believe good leadership starts with dignity
We believe every person leading a team deserves the same rigor and care they're expected to give everyone else — especially in the moments when the stakes are highest and support is hardest to find. Sustainable growth happens when a leader's strategy and their team's culture are actually pulling in the same direction, not just aligned on paper. We've built our work around helping leaders get there, especially when the pressure is real and the timeline is short.
• Our Guiding Values
What we hold to in every engagement
Not just the ones that go easily.
Partnership
We believe in the power of our partnerships to bring out the best in our clients, colleagues, and communities.
Imagination
We believe in changing the questions to find the best answers.
Growth
We believe human flourishing comes from a growth mindset, inside and out.
Imperfection
We believe that embracing imperfection leads to freedom and creativity.
Joy
We bring the energy to spark joy in all we do.
• Our Team
The people behind the work
Dr. Philipia Hillman
Founder & CEO
Allison Abayasekara
Strategy & Culture Alignment Coach
Amanda Graham
Organization Strategist & Leadership Consultant
Dr. Yasemin Gokalp
Executive Performance & Culture Coach
Jennifer Vanmeter
Executive Coach & Strategy Consultant
John Ryabik
Strategist & Executive Coach
Loraine Trotter
Executive Coach
Monica Brewster
Organizational Strategist & Facilitator
Nick Jivasantikarn
Strategy and Operations Leader
Philip Hillman
Executive Coach
Dr. Steven Jones
Executive Coach & Consultant
See where your own team stands
Four things that only work when they're pulling in the same direction, especially under pressure.
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