Erika Benadom

Planned break following Zensai, used to go deep on applied AI and build a public body of Chief of Staff work.

• •Built ehbenadom.com end-to-end on Lovable using natural-language prompting, including 10 original Chief of Staff frameworks, dynamic content, and custom design; the site is itself the proof of AI-first operator capability rather than a description of it.
• •Ran hands-on evaluation of the operator AI stack, including Claude, Comet, and Synthesia among others, testing each against real executive-operations work: meeting preparation, research synthesis, communications drafting, and action-item triage.
• •Translated tool capability into repeatable operating process, designing multi-step AI workflows for the recurring work a Chief of Staff actually owns rather than experimenting for its own sake.
• •Published original frameworks and research on organizational AI adoption, including analysis of why enterprise adoption programs stall on psychology and change management rather than on technology.

Zensai is a global HRtech SaaS company serving 5M+ learners across enterprise customers worldwide.

• •Served as confidant and operational right hand to the CEO on company, investor, and staff matters with full board and executive access, trusted on every high-stakes decision spanning a 200+ person organization across 7 countries.
• •Designed and ran the company-wide operating cadence (annual OKRs, quarterly business reviews, weekly leadership team meetings, monthly executive reporting) aligning 10 c-suite leaders and 200+ employees on shared priorities, with 85%+ on-time completion of executive action items across quarterly cycles.
• •Owned board and shareholder relations end-to-end, delivering 4+ board cycles per year through Nasdaq Boardvantage with 100% on-time materials and zero governance escalations across 8+ consecutive cycles; coordinated in-person strategy days and supported investor communications.
• •Led the Operational Leadership Team across GTM, Product, and regional functions, setting agendas, driving follow-through, and aligning leaders on shared execution priorities to keep cross-regional initiatives on schedule.
• •Built Zensai's AI Hub and shipped the company's first Copilot Studio agent, deploying AI-powered tools for OKR alignment with company-wide adoption within 6 months of launch.
• •Directed company-wide events and executive workshops including the Human Success Summit (200+ attendees, 9.2/10 attendee rating) and regional leadership offsites across all 7 markets, owning agenda design, content, vendors, and follow-through on budget.
• •Led a complex 12-month HQ relocation from site evaluation through stabilization, coordinating 15+ vendors and 8 cross-functional workstreams across real estate, IT, facilities, legal, and people operations with full safety and compliance handoff and zero days of business disruption.
• •Established and operated regional office infrastructure across Poland, Romania, Germany, Australia, the UK, Denmark, and the US, supporting 200+ employees and setting consistent operating standards that reduced HQ bottlenecks on regional decisions.

Ridge is a Series A venture capital firm with $600M+ AUM; portfolio includes 100+ companies across enterprise software and AI.

• •Maintained partner operating rhythm through weekly portfolio reviews, pipeline meetings, board preparation, and action tracking; a direct precursor to Chief of Staff-level operating work.
• •Managed high-stakes investor events and executive roundtables for founders and LPs, owning every logistics and communications detail from invite to follow-up.
• •Owned CRM data integrity (Affinity), dealflow documentation, and process design across the investment team; recruited and managed a dedicated data specialist.
• •Produced VC portfolio prep briefs, ghostwrote LinkedIn articles for partners, and crafted external communications representing the firm to founders, LPs, and co-investors.
• •Managed sensitive and confidential matters including banking wire coordination and LP communications, with zero margin for error.

WeWork at peak scale — 500,000+ members, operating in 100+ cities globally.

• •Strategic thought partner to the Global CMO inside a high-velocity, high-visibility organization; operated as communications proxy, fielding outreach from a global marketing org.
• •Coordinated global Marketing and GTM leadership offsites, all-hands, and executive summits, owning agenda design, content coordination, AV, facilities, and follow-through.
• •Drafted internal communications to the global marketing org and curated content for monthly newsletter; managed the CMO's global calendar, international travel, and executive presence.

• •General manager of an 800-student, 50-staff K–6 campus with full P&L accountability; ran the operating rhythm, set strategy, managed budget, and owned outcomes.

• •Brought in to lead a high-challenge turnaround; performance-managed underperforming staff, restructured the leadership team, and galvanized the organization around a shared mission.

• •Directed district-wide digital transformation across multiple sites — managed infrastructure (CAT6, fiber, wireless, VOIP), led a team of 16, and oversaw multi-year technology contracts.
• •Partnered with architects and construction firms on technology readiness for newly built and renovated campuses; served as technology strategy advisor to district executives.