Executive Assistant to the CEO (Remote)

REI BlackBook is a fast-growing SaaS platform helping real estate investors simplify financial freedom through systems, software, and education. We’re scaling from founder-driven to leadership-driven — and the CEO needs a strategic right hand who can translate vision into action, protect focus, and create follow-through across the company. This is not a traditional administrative role. This is a Force Multiplier position — part Executive Assistant, part Chief of Staff Lite, and part operator. You’ll bring order to chaos, clarity to motion, and accountability to ideas.

PURPOSE - Your mission is to buy back the CEO's time and ensure flawless execution of priorities across the organization. You’ll capture decisions, manage communication flow, enforce organizational rhythm, and act as the connective tissue between Damon, the leadership team, and key partners.

CORE OUTCOMES - Within 90 days, success means:

1. The CEO’s time and attention are spent on vision, strategy, and relationships — not administration.

2. Every decision, action, and commitment is documented, owned, and completed.

3. Leadership rhythms (weekly, monthly, quarterly) run on time with clear outcomes.

4. Damon’s communication channels are clear, filtered, and aligned with priorities.

5. 10+ hours per week of low-value activity have been eliminated, delegated, or automated.

KEY RESPONSIBILITIES

1. DECISION FLOW OWNERSHIP

● Capture every decision the CEO makes (verbally, in Slack, meetings, or email).

● Translate each decision into clear, assigned actions with due dates.

● Track progress and close the loop to confirm completion.

● Maintain a living “CEO Priority Tracker” to ensure every commitment is visible, updated, and measurable

● Serve as the single point of accountability for decision execution.

2. CONTEXT GATEKEEPING

● Serve as the gatekeeper for the CEO's time and attention, filtering information, requests, and opportunities through strategic context — not availability.

● Control the inflow of meetings, calls, and requests; determine what requires the CEO's input and what can be delegated.

● Manage information velocity — ensure the CEO sees only what’s essential and when he needs to see it.

● No external or internal meeting is scheduled without passing through this context filter.

3. STRUCTURED RHYTHM ENFORCEMENT

● Own the organizational rhythm that keeps REI BlackBook aligned and accountable.

● Schedule and prepare for all weekly leadership syncs, quarterly planning sessions, and annual reviews.

● Distribute meeting agendas at least 48 hours in advance; publish follow-up notes and next steps within 24 hours.

● Maintain the company scorecard or OKR dashboard, ensuring all deliverables are updated weekly.

● Partner with the Integrator to ensure the company runs on cadence, not chaos.

4. CONFIDENTIAL CHIEF OF STAFF LITE

● Partner closely with the Integrator to align the CEO's strategic priorities and commitments with company objectives.

● Manage confidential communication and sensitive information with discretion and professionalism.

● Coordinate cross-functional execution between the CEO, the Integrator, and department heads — ensuring alignment, not overlap.

● Act as the CEO's operational translator — turning ideas into structured action and ensuring they connect back to company goals.

5. OUTCOME-BASED SCORECARD

Own measurable outcomes, not just activity:

● 100% of CEO priorities documented and tracked weekly.

● Inbox triaged daily with fewer than 10 pending actionable items.

● 24-hour turnaround on meeting follow-ups.

● 90%+ of commitments completed on time. ● 80%+ calendar alignment with the CEO's “Perfect Week.”

● Monthly Buyback Report showing hours reclaimed and processes improved.

6. CONFLICT AND FEEDBACK CADENCE

● Maintain a standing bi-weekly CEO + EA alignment session focused on priorities, blind spots, and communication friction.

● Provide direct, candid feedback when priorities conflict or decisions stall.

● Hold space for honesty and accountability — candor and trust are non-negotiable.

● Document all alignment notes to ensure clarity and mutual understanding.

7. BRAND & VISIBILITY MANAGEMENT

● Manage all logistics and prep for the CEO's external appearances, podcasts, Bootcamps, and speaking engagements.

● Coordinate with the marketing team to ensure brand alignment across social posts, partner features, and events.

● Oversee post-event follow-ups and action tracking to convert opportunities into outcomes.

● Ensure CEO's public presence is consistent, credible, and strategically leveraged.

8. INTEGRATION WITH THE OPS LAYER

● Report directly to the CEO, while maintaining operational alignment with the Integrator for execution rhythm.

● Ensure seamless communication between the CEO and the Integrator — no duplication, no missed context.

● Sync weekly with the Integrator to review company scorecards, decisions in flight, and priorities requiring the CEO's input.

● Support cross-functional coordination between leadership teams, ensuring the company moves in one direction.

9. PERSONAL DOMAIN SUPPORT

● Coordinate limited personal logistics (family travel, key events, calendar alignment) to support holistic energy and time management.

● Maintain strict confidentiality and professionalism when managing personal matters.

● Manage integrated scheduling across business and personal commitments to avoid conflicts or overload.

● Expected time allocation: ~90% business / 10% personal support.

10. AUTHORITY CLARIFICATION

Operate within an explicit authority matrix:

Level 1 – Independent Authority

● Schedule management, internal meeting approvals, standard correspondence.

Level 2 – Conditional Authority

● External responses, travel, and vendor decisions under approved budgets.

Level 3 – CEO Review Required

● Strategic partnerships, contractual decisions, or financial commitments above threshold. You are empowered to act on Damon’s behalf within these boundaries to ensure speed without sacrificing trust.

WHO YOU ARE

● Execution-Obsessed: You don’t just track actions — you close them.

● Strategically Minded: You see the big picture but know how to operationalize it.

● Relentlessly Organized: Systems, checklists, and follow-through are your superpowers.

● Calm Under Pressure: You’re the steady hand in a fast-moving environment.

● Candid Communicator: You value truth over comfort and clarity over ambiguity.

● Tech Fluent: Skilled with ClickUp, Slack, Google Workspace, HubSpot, and automation tools.

● Loyal and Discreet: Trusted with sensitive information and high-stakes communication.

● Proactive Problem Solver: You anticipate needs before they’re spoken.

MEASURABLE SUCCESS INDICATORS

● 90%+ of tracked commitments delivered on time.

● Inbox and calendar maintained within defined thresholds.

● Leadership rhythm executed without delay or duplication.

● The CEO's operational time reduced by at least 50% within six months.

● Company-wide feedback: “Nothing falls through the cracks.”

EXPERIENCE & FIT

● 3–5+ years supporting a founder or CEO in a high-growth company.

● Proven ability to manage cross-functional coordination and decision flow.

● Exceptional written and verbal communication skills.

● Comfortable operating with autonomy in a fast-paced, low-formality culture.

● SaaS or real estate industry experience preferred but not required.

WHY THIS ROLE MATTERS

REI BlackBook’s mission is to simplify financial freedom — for investors and for our team.

Your role enables that mission by freeing the CEO's to operate in his genius zone: vision, innovation, and growth. When this role is done right, the company moves faster, communication flows clearly, and execution happens without chaos. You won’t just be an assistant. You’ll be the operational heartbeat behind the vision.

Pay: Php40,000.00 - Php60,000.00 per month

Benefits:

• Flexible schedule
• Flextime
• Opportunities for promotion
• Paid training
• Pay raise
• Work from home

Application Question(s):

• Do you have SaaS or real estate experience?

Education:

• Bachelor's (Required)

Experience:

• Executive Assistant: 3 years (Required)

Language:

• English (Required)

Location:

• Philippines (Required)

Work Location: Remote