President, Ladderspot | A Growth Marketing Agency | Former CMO at Boeing | Former US Diplomat, Veteran

I have spent more than 20 years leading GTM and marketing operations in environments where timing, precision, and accountability were non-negotiable. My path runs through AI platforms, commercial SaaS launches, defense technology portfolios, and enterprise transformations that required structure, clarity, and budgets that held under real scrutiny. I have built GTM systems that connect spend to revenue outcomes, create predictable operating cadence, and ensure leadership has full visibility into what is working, what is stalling, and what requires a reset.

My experience includes serving as CMO of Viasat Defense during its rapid revenue expansion from 900M to 1.3B, leading Boeing’s brand and venture portfolio realignment during its most public inflection point and founding a VC-backed AI adtech platform by prioritizing attribution accuracy, launch logic, and sustained customer adoption. Before that, I built and scaled a GTM agency from zero to 15M ARR and served as a Diplomat and Senior Army Strategist, where communication alignment and operating rhythm mattered in ways that shaped how I approach this work today.

I focus on building systems that allow organizations to scale without sacrificing clarity. I work closely with CMOs, CFOs, CROs and RevOps to ensure marketing is not a creative function sitting apart from revenue, but a disciplined engine aligned to pipeline maturity, ARR targets, and executive decision cycles. I am at my best when expectations are high, measurement is clear, and the work requires translating complexity into something that can withstand real operational pressure.

If your organization is looking for leadership that treats GTM as the connective structure between investment and outcome, I would welcome the chance to connect.

📫 I look forward to connecting with you here on LinkedIn or at sgilfillan@gmail.com

I get so many questions on Federal GTM that I joined Hubble so I could open up a few 1:1 spots - a space built for thoughtful conversations and honest advice.

If you’ve been struggling with Federal BD or GTM, trying to think through hiring, senior advisors, have questions about how the Federal buying center works (there are 7 geographically dispersed roles per capture), growing something new, navigating a pivot, or just need clarity, this is your chance to book some time with me. Excited to connect and I’d love to support however I can.

I can help with:
✔️ Public Sector GTM Strategy
✔️ Federal & Defense Market Entry
✔️ Regulated Enterprise Communications
✔️ How to Build and Grow a Federal GTM team
✔️ Senior Leader or Federal GTM Vetting

👉 Book now:

Sean  Gilfillan 

Founder of REX, BaseFEST | VP / Director – Public Sector GTM, Marketing & Communications | Former U.S. Diplomat | Army Officer | Defense Contractor

Open article: Hubble | Schedule with Sean Gilfillan by app.hubble.social

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