Erika Benadom
Executive Operations & Transformation Leader
Driving executive operating rhythms, strategic programs, and cross‑functional execution for high‑growth SaaS, GTM, and Education organizations.
Profile
About Me
Senior business operations and Chief of Staff–style leader who serves as a trusted confidant to CEOs and senior executives, bringing structure, judgment, and discretion to complex, high‑stakes work. I turn institutional and organizational transformation into executable plans across education, venture‑backed tech, and global SaaS, keeping stakeholders aligned, accountable, and genuinely bought in. I'm known for combining rigorous operating discipline with optimism, empathy, and strong executive presence, so that ambitious change feels both possible and energizing for the teams involved.
Core Competencies
- Executive partner and trusted confidant to CEOs and senior leaders on company, investor, and staff matters.
- Design and leadership of executive operating rhythms (OKRs, quarterly reviews, leadership meetings, board and shareholder reporting) that drive clarity and accountability.
- Transformation and change leadership across education systems, venture‑backed tech, and global SaaS, including institutional and service redesign.
- Strong financial acumen: complex budget oversight, business cases, value‑for‑money decisions, and transparent reporting.
- Governance, risk, and delivery discipline that brings structure to complicated issues without overcomplicating them.
- Ability to synthesize complex information, anticipate executive needs, and coordinate multi‑site, cross‑regional programs where failure is not an option.
- Builder mentality with curiosity, adaptability, attention to detail, and execution precision in fast‑paced environments.
- High‑trust leadership style that combines optimism, empathy, and clear communication, keeping demanding stakeholders engaged and bought in.

Robin Daniels
"I've hired Erika Benadom twice because when the stakes are high and the margin for error is zero, she's the person I want by my side turning chaos into clarity and execution into results. Erika is a rare blend of heart and horsepower: people trust her instinctively, she gets the hard things done without drama, and she moves seamlessly between big-picture strategy and hands-on delivery. If you get the chance to work with her, take it — your team, and your business, will be better for it."
Chief Business Officer · 3x CMO · ex Salesforce, WeWork, LinkedIn, Box
Current RoleSenior Executive Business Partner to the CEO at AI GEO Start-up · May 2026 – Present
- Serve as the CEO's executive business partner and operational proxy, trusted to represent the founder with customers, partners, vendors, and internal stakeholders.
- Enable GTM velocity by sourcing, organizing, and shepherding procurement documentation through review cycles, removing friction from sales and partnership close processes.
- Ghostwrite and route executive communications on behalf of the CEO to customers, partners, and vendors — preserving tone, urgency, and relationship continuity.
- Execute partnership and equity contracts end-to-end, coordinating legal, finance, and counterparties to keep complex deals moving to signature.
- Built a live sales pipeline dashboard (with AI assistance) that visualizes Slack-tracked prospects and customers, updating multiple times daily to inform CEO-level revenue decisions.
- Automate recurring executive workflows — daily CEO agenda rundowns, Linear issue updates, and rolling task lists — freeing the CEO for higher-leverage strategic work.
- Act as board liaison, establishing meeting cadence, drafting minutes, and owning follow-up communications to maintain governance momentum and accountability.
- Provide remote executive support at high-profile events such as the Cannes Marketing Festival, arranging just-in-time meetings and real-time logistics.
- Lead the security and compliance workstream to achieve SOC 2 and ISO 27001 certification, coordinating auditors, evidence collection, and cross-functional readiness.
Testimonials from Zensai Colleagues
"Thank you for all your energy and hard work you did behind the scenes. I'm not sure that even altogether we could match this level of excitement you brought. You never JUST did your job, you put your heart into everything. Trust me, this inspired many of us."
"It has been an absolute pleasure working with you this past couple of years. I have learnt a hell of a lot from you and you are one of the very few people in the world that genuinely goes above and beyond for people, not as a job but just as an awesome Human. Will always remember everything you have brought to Zensai, you will always be part of our journey."
"There's nothing quite like being thrown in at the deep end to solidify a friendship. Your calm yet forceful nature are what stand out to me. You are a true inspiration, and I often recount the mantra when I'm feeling stuck or indecisive. Thank YOU for being YOU."
"I hope paths will cross again at some time. Thank you for our discussions, your relentless energy and focus and for your tremendous help in pushing things forward. You have had a huge impact in my path as well, and I am hugely grateful for that."
"You have shown us a whole different level of true engagement and giving it all for the Zensai team. You have been so incredibly giving and an inspiration. You will be so missed and not least for your personality, your hard work and for always bringing fun and light. You are so brave and took a chance on us."
Portfolio
Work Samples
Selected examples of operating rhythms, programs, and strategic initiatives — evidence of executive operations and cross-functional leadership.
№ 01Operating RhythmsStrategic Planning Frameworks
Comprehensive framework for aligning executive priorities with cross-functional execution — OKR implementation, quarterly planning cadences, and leadership operating rhythms.
Read the case
№ 02Program & Event DeliveryGlobal Events & Conference Operations
End-to-end program management for company-wide events (Human Success Summit, 200+ attendees, 9.2/10 rating): agenda design, speaker coordination, venue services, and post-event follow-through.
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№ 03Cross-Functional InitiativesAI Agent & Hub Creation
Built Zensai's AI Hub and shipped the company's first Copilot Studio agent — empowering 200+ employees with AI-powered tools for OKR alignment and strategy access.
Read the case
№ 04Program Management12-Month HQ Relocation Program
Managed end-to-end workplace build-out across 15+ vendors and 8 cross-functional workstreams — with zero days of business disruption.
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№ 05Executive CommunicationBoard & Investor Relations
Managed board governance through Nasdaq Boardvantage, coordinating in-person strategy days, executive roundtables, and investor relations during fundraising activities.
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№ 06International OperationsPoland Office Setup & Regional Operations
Planned and delivered regional expansion: coordination with local teams, vendor management, and onsite QA for international team meetings.
Read the case
Career
Professional Experience
Corporate Experience
AI GEO Start-up
Senior Executive Business Partner to the CEO
AI-powered geospatial technology startup building data-driven solutions for global customers.
- •Serve as the CEO's executive business partner and operational proxy, trusted to represent the founder with customers, partners, vendors, and internal stakeholders.
- •Enable GTM velocity by sourcing, organizing, and shepherding procurement documentation through review cycles, removing friction from sales and partnership close processes.
- •Ghostwrite and route executive communications on behalf of the CEO to customers, partners, and vendors — preserving tone, urgency, and relationship continuity.
- •Execute partnership and equity contracts end-to-end, coordinating legal, finance, and counterparties to keep complex deals moving to signature.
- •Built a live sales pipeline dashboard (with AI assistance) that visualized all Slack-tracked prospects and customers, updating multiple times daily to give the CEO a real-time view of revenue momentum.
- •Automated recurring executive workflows — daily CEO agenda rundowns, Linear issue updates, and rolling task lists — freeing the CEO for higher-leverage strategic work.
- •Act as board liaison, establishing meeting cadence, drafting minutes, and owning follow-up communications to maintain governance momentum and accountability.
- •Provided remote executive support at the Cannes Marketing Festival, arranging just-in-time meetings and real-time logistics in a high-profile, fast-moving environment.
- •Lead the security and compliance workstream to achieve SOC 2 and ISO 27001 certification, coordinating auditors, evidence collection, and cross-functional readiness.
Zensai
Head of Executive & Regional Operations
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, strategy access, and daily workflow leverage to 200+ employees 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 Ventures
Executive & Operations Partner to 3 Partners
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
Executive Assistant to Global CMO
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.
Dwellsy
Marketing Manager
Venture-backed proptech startup.
- •Partnered with founders to build early go-to-market motion through paid campaigns, content programs, and brand positioning at a venture-backed proptech startup.
Leadership & Institutional Operations
Prior to transitioning to tech, Erika held P&L-accountable general management roles leading 40–50-person organizations, managing multimillion-dollar budgets, and driving institutional transformation — experience that directly informs her operating discipline and change leadership today.
Los Altos School District
Principal, Almond Elementary
- •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.
Morgan Hill School District
Principal, Paradise Valley Elementary
- •Brought in to lead a high-challenge turnaround; performance-managed underperforming staff, restructured the leadership team, and galvanized the organization around a shared mission.
Lennox School District
Director of Technology & EdTech Assessment Coordinator
- •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.
Writing
Insights & Voice
Writing on sensemaking, operating rhythms, and the quiet structures that keep Education, Sales, and Customer Success organizations moving.
The Power of Sensemaking
On supporting senior leaders by turning noisy inputs from GTM, Education, and CS teams into clear priorities and decisions.
November 23, 2025
"In every fast-moving organization, there's a quiet moment that determines everything. When information is swirling, priorities shifting, and everyone is moving fast — someone has to make sense of the chaos."
What Chief of Staff Really Means
Defining the role that bridges strategy and execution across global Education, Sales, and Customer Success teams.
November 19, 2025
"Most people misunderstand the Chief of Staff role. They think it's calendars, comms, and coordination. In reality, the best Chiefs of Staff focus on creating clarity where ambiguity lives, alignment where silos form, and momentum where decisions stall."
Operating Rhythms That Transform Teams
Practical examples of weekly leadership cadences, QBRs, and skip‑level forums that keep global teams aligned.
November 17, 2025
"The biggest gap inside fast-moving organizations isn't intelligence or effort. It's structure. The kind that turns vision into execution, and execution into results."
"The ability to turn noise into clarity. To weave together the signals from teams, the context from leadership, the constraints no one wants to say out loud, and the opportunities hiding between the lines."
— On the art of sensemaking




