Fort Lauderdale, Florida, United States
Most people tell you what you want to hear. I tell you what you need to know - and most executives get the same deal. I have spent 28 years showing up for people in the moments that matter most: turning around a $273K institutional deficit without a single layoff, leading a condominium community through COVID lockdown as its Board President (completing a mandatory 50-year structural inspection with zero deficiencies along the way), and delivering 10 months of crisis counseling after 9/11. The through-line is the same everywhere: I find the gap between what a leader needs and what currently exists, and I close it. My career has spanned two Catholic dioceses in New York, enterprise SaaS (Blackbaud), wellness coaching, and independent consulting - but the function has always been the same. I build operational infrastructure from scratch. I drive executive communications strategy. I manage the work that crosses team lines without waiting to be directed. For 11 years at the Archdiocese of New York I did exactly that: produced a 16-page weekly publication for 7,000 households, rebuilt a failing preschool in six weeks, and built a $340K digital relief platform in 48 hours after Hurricane Sandy. The last two years added a new dimension. I am now an AI-native operator who builds, not just uses, these tools. I shipped a 3-site AI-powered career strategy platform with automated intake and payment matching. I built a 14-part SOP infrastructure for a multi-state law firm using Claude, Google Apps Script, and Zapier. The shift from user to builder happened fast, and it changed what I consider possible. I'm currently focused on Chief of Staff, VP/Director of Operations, and VP Client Success roles at mission-driven organizations, SaaS companies, and legal/professional services firms - remote or based in Fort Lauderdale, FL. I also advise on real estate and community association governance as a licensed Florida Realtor® and CAM, and I hold dual US and UK citizenship. Currently building: Redirect (AI-powered career navigation platform) - The Truth Shall Make You Free (memoir, 2027). Facts over speculation. Clarity over noise.
6-month organizational transformation engagement serving as the principal's primary thought partner and operational force multiplier across a multi-jurisdictional practice. Serve as the principal's strategic thought partner — owning cross-functional execution, leading initiatives that cross team lines, and managing the work that doesn't fit neatly into any other box. Drive all executive communications strategy: team announcements, the inaugural Shanahan Brief client newsletter, onboarding narratives, and firm-wide SOPs adopted as operating standards. Built a full AI-native operations infrastructure from scratch: 14-part SOP Master, New Hire Onboarding Guide, Team Guide (v5), RingCentral VoIP integration playbook, and a 30/60/90-day milestone framework — deployed to a globally distributed team across three continents. Deployed Claude, Google Apps Script, and Zapier to automate intake workflows, eliminate manual follow-up bottlenecks, and reduce onboarding friction across a team spanning India, Argentina, and the US. Manage vendor relationships and staff transitions, including bookkeeper onboarding, ensuring operational continuity through the full engagement lifecycle.
Fractional Chief of Staff and COO consulting, AI workflow transformation, and executive communications strategy for mission-driven organizations, law firms, and professional services clients. Serve mission-driven organizations, professional services firms, and executives as an AI-native operations consultant — deploying Claude, ChatGPT, and Gemini to automate legacy workflows, build scalable internal systems, and multiply team efficiency. Provide fractional Chief of Staff and COO support: own cross-functional execution, lead special projects, and drive executive communications strategy across newsletters, stakeholder announcements, and board-level content. Built Redirect — a 3-site React/Vercel AI-powered career strategy platform (Gillen Ventures LLC) with automated intake, Google Sheets backend, Zelle payment matching, and a password-protected client portal. Actively building toward launch. Directed full digital infrastructure builds for legal practice clients: AI-native workflows, automated client intake, platform integrations (Lawmatics, Clio, Bambiz, RingCentral), and SOP suites adopted as firm standards. Former Fiduciary Board President, Victoria Park Tower HOA: led the association through the COVID-19 lockdown and completed the mandatory 50-Year Structural Inspection in 2021 with zero deficiencies — experience that directly informs CAM advisory work today.
Advising condominium and homeowner associations on governance, compliance, and Florida's evolving community association law framework. Licensed Florida CAM (#CAM59384): advise condominium associations on governance, reserve fund strategy, vendor management, ethical board conduct, and Florida Milestone Inspection and SIRS compliance. Active CAM advisory clients include Victoria Park Condo Association (Fort Lauderdale) — providing ongoing guidance on governance, compliance, vendor management, and reserve fund strategy. Serve as community liaison on behalf of Americas on the Park Condo Association to the Central Beach Alliance — representing association interests in neighborhood planning, civic engagement, and beach corridor development. Former Fiduciary Board President (Victoria Park Tower HOA), Treasurer (Bears of South Florida), and Director across multiple associations — bring governance experience from inside the boardroom, not just from the outside.
"Most agents tell you what you want to hear. John Gillen tells you what you need to know." — No-Nonsense Navigator · Let Gillen Guide You. Licensed Florida Realtor® (#SL-3445594) affiliated with Better Homes and Gardens Real Estate | Florida 1st (777 S Federal Hwy, Fort Lauderdale, FL 33316). $2,000,000 Club member across multiple consecutive production years in Broward and Miami-Dade counties. Represent buyers, sellers, and investors across Fort Lauderdale, Wilton Manors, Pompano Beach, Oakland Park, and surrounding Broward communities — with deep expertise in condominiums, HOA-governed communities, and Intracoastal properties. Post-Surfside condo legislation specialist: advise clients on Milestone Inspection requirements, Structural Integrity Reserve Studies (SIRS), special assessments, and Florida Statute 718.504 disclosure obligations across SB 4-D, SB 154, HB 1021 (Condo 3.0), and HB 913. Accredited Buyer's Representative® (ABR®) and At Home with Diversity® (AHWD®) certified — every client deserves a trained advocate and a transaction that feels as good as the property. Integrate AI research tools into every transaction — sharper market analysis, faster comps, smarter preparation — while keeping every client relationship fully, deliberately human.
Eight-year concurrent engagement delivering structured behavioral change facilitation for national and international audiences. Designed and facilitated group and one-on-one coaching applying adult learning methodology, motivational interviewing, and behavioral change frameworks grounded in M.S. Counselor Education training. Selected for 5 international chartered cruise programs (2018-2020) — a historic initiative spanning 5 countries, uniting participants across the US and abroad around evidence-based habits of nutrition, activity, sleep, and community. Served as an inaugural virtual coach during the COVID-19 transition: designed new digital program structures and accountability protocols with zero lead time; model adopted as WW's virtual delivery standard. Designed a cascading training model that translated proprietary corporate content into locally deliverable formats for regional guides, maintaining program fidelity across the national network.
Leading SaaS provider serving 45,000+ nonprofits — Raiser's Edge, Financial Edge, Smart Aid, Smart Tuition Managed a $1.7M+ ARR portfolio across 600 mission-driven enterprise clients and 35,000+ individual accounts; consistently maintained top-tier performance rankings for retention and revenue growth. Conceptualized and launched the "Daily 7 Call" proactive client engagement model — adopted enterprise-wide as the benchmark standard for reducing churn and accelerating time-to-value. Spearheaded Smart Aid and Smart Tuition financial aid platform evolution from incubation to flagship SaaS products; drove a 40% improvement in application-processing speed by converting manual workflows into automated features. Built and deployed targeted enablement programs that drove a 20% product utilization increase across the portfolio. Ensured 100% service continuity during a catastrophic platform failure by manually processing 21,000+ sensitive communications across a 120-language global portfolio.