Executive Assistant

EXECUTIVE ASSISTANT TO FOUNDER & CEO Nonprofit Operations, Grants, Client and Compliance Support Cornerstone Youth Collective is seeking a highly capable Executive Assistant who can provide substantive operational support to the Founder and CEO of a growing nonprofit social-services organization. This is not a light calendar-management position. This is not a personal-assistant position. This is not a role for someone who waits for the CEO to identify, explain, remind, and quality-check every administrative step. The Executive Assistant will support executive operations across grants, client services, compliance, contracts, board administration, vendors, programs, documentation, meetings, and organizational systems. ABOUT CORNERSTONE YOUTH COLLECTIVE Cornerstone Youth Collective is a Black, Native, and woman-owned nonprofit serving underrepresented communities, particularly African American, Latino, and Native American individuals and families. CYC provides housing support, intensive case-management services, employment and education support, health and harm-reduction resources, foster-youth support, emergency response, and community resource navigation. Our operating model is: • Low barrier • Housing First • Client centered • Trauma informed • Documentation driven • Compliance conscious • Mission focused ABOUT THE FOUNDER AND THE POSITION CYC was founded and built from the ground up by its Founder and CEO. The Founder did not inherit an established staff, administrative department, development office, compliance department, or operational infrastructure. She created the programs, systems, policies, procedures, partnerships, grant pipeline, and service-delivery structure while also serving clients and managing the organization. The Founder and CEO continues to: • Hold and support active clients • Write grant applications and funding narratives • Develop programs and operating procedures • Prepare government, nonprofit, and compliance filings • Manage contracts, funders, vendors, and partnerships • Oversee organizational finances and reporting • Lead board and executive operations • Resolve frontline operational problems The Executive Assistant is being hired to materially increase the Founder’s capacity. You will not be supporting an executive who is disconnected from the work. The CEO knows how to perform the functions being delegated and has documented the required processes. You will be expected to read those documents, understand the organizational context, follow established procedures, anticipate the next administrative step, and close work without requiring the CEO to repeatedly restate written instructions. THE ROLE The Executive Assistant is responsible for maintaining operational continuity around the Founder and CEO. Your responsibility is to ensure that: • Critical communications are not missed • Deadlines are visible and actively managed • Meetings are properly scheduled and prepared • Client administrative workflows continue moving • Grant opportunities are researched and prepared for CEO review • Documents are collected, named, filed, and retrievable • Board, vendor, partner, and program records remain current • Compliance concerns are documented and escalated • Assigned work is completed with evidence • The CEO is not pulled back into preventable administrative disorder This is a working Executive Assistant role. The successful contractor must be willing and able to move between executive support, project coordination, document analysis, client administration, grant preparation, and compliance support during the same workweek. CORE RESPONSIBILITIES 1. EXECUTIVE OPERATIONS • Manage the CEO’s calendar, meeting requests, reminders, preparation blocks, deadlines, and follow-up items. • Review the calendar daily for additions, changes, cancellations, conflicts, missing links, and unconfirmed meetings. • Protect time for client work, grant production, filings, financial review, board preparation, contracts, and executive decision-making. • Schedule internal and external meetings with complete titles, attendees, time zones, conferencing links, agendas, and relevant document links. • Offer two or three alternative times when resolving scheduling conflicts. • Respond to urgent scheduling changes within one business hour. • Maintain accurate recurring meetings and review recurring schedules monthly. • Prepare the CEO for upcoming meetings by gathering the relevant correspondence, documents, background information, and unresolved decisions. • Identify what requires CEO action rather than forwarding an unorganized stream of information. 2. EMAIL AND COMMUNICATION MANAGEMENT • Review assigned organizational and executive inboxes during agreed working hours. • Prioritize communications involving funders, government agencies, contracts, compliance, clients, board members, vendors, deadlines, and partnerships. • Respond to routine administrative matters within 24 hours. • Draft professional responses for CEO review when executive approval is required. • Send an authorized neutral acknowledgment when a complete response cannot yet be provided. • Prevent important correspondence from remaining unanswered beyond 48 hours. • Escalate funding deadlines, compliance timelines, contract risks, legal notices, client safety concerns, and high-stakes partner communications immediately. • Maintain clear records of the sender, subject, required action, action taken, and outstanding follow-up. • Never represent yourself as the CEO or issue an executive commitment without authorization. 3. TASK AND PROJECT MANAGEMENT • Use ClickUp as the official task, documentation, and accountability system. • Acknowledge assigned work during the same working day. • Ask necessary questions early rather than waiting until a deadline is at risk. • Maintain accurate task statuses, owners, deadlines, dependencies, and supporting links. • Break multi-step assignments into clear and trackable actions. • Update blocked work with the specific obstacle, steps already taken, and decision or resource required. • Follow assigned work through completion rather than performing only the first visible step. • Create and maintain task structures for grants, programs, events, board actions, vendors, clients, audits, and organizational initiatives. • Keep urgent communication in Google Chat while ensuring the underlying work and evidence remain documented in ClickUp. • Do not create private spreadsheets, informal lists, or parallel systems that leadership cannot access. 4. CLIENT ADMINISTRATIVE SUPPORT This is not a clinical role, but it is a client-facing role. The Executive Assistant may support clients with administrative and resource-navigation activities, including: • Preparing intake packets and required forms • Creating and maintaining secure client folders • Requesting identification, income verification, benefit letters, housing records, insurance information, releases, consents, and other required documentation • Pre-filling approved forms while leaving signature and attestation fields for the appropriate person • Scheduling intake appointments, application calls, check-ins, and support meetings • Sending appointment confirmations and reminders • Assisting clients with housing, employment, benefit, or program applications • Coordinating approved background-check processes • Saving application confirmations, receipts, and submission evidence • Tracking missing documents and application requirements • Following up on pending applications and background-check results • Logging communication attempts, responses, outcomes, and next steps • Escalating nonresponsive clients after the required number of documented attempts • Supporting Address Confidentiality Program, DSHS, or other high-risk workflows under enhanced security procedures Every client-related action must be documented. Client work may not remain only in email, text messages, personal notes, or memory. The Executive Assistant may not provide legal, clinical, therapeutic, or medical advice. 5. GRANT RESEARCH AND APPLICATION SUPPORT Grant administration is a recurring and material part of this position. The Executive Assistant will be expected to: • Conduct a daily grant-opportunity review using approved funding sources. • Conduct a more extensive weekly search for foundation, government, capacity-building, service, housing, youth, behavioral-health, reentry, and public-contract opportunities. • Verify opportunities through the original funder or government source. • Determine whether CYC meets the stated nonprofit, geographic, programmatic, award, deadline, and documentation requirements. • Exclude expired, invitation-only, individual-only, geographically ineligible, or otherwise unqualified opportunities. • Record all required information in the grant-tracking system without leaving fields blank. • Save dated proof of the live opportunity. • Create the required Google Drive folder and supporting documents. • Extract all application questions and preserve word or character limits. • Create a checklist of required attachments. • Review prior CYC proposals and identify relevant examples. • Prepare a concise fit, risk, and go/no-go recommendation. • Create accurate deadline events, preparation blocks, and document-assembly reminders on the CEO’s calendar. • Track webinars, letters of intent, partner requirements, portal registrations, matching requirements, audited-financial requirements, and reporting obligations. • Maintain a live qualified funding pipeline. • Prepare complete pre-application packages so the CEO can move directly into writing and decision-making. • Support application submission after CEO approval when specifically authorized. • Save confirmations and maintain post-submission and reporting deadlines. The CEO retains responsibility for final funding decisions, core narrative authorship, budget approval, certifications, and final sign-off unless authority is expressly delegated. Immediate escalation is required when: • A deadline is seven days or fewer away • A substantial funding opportunity is identified • Partners, coalitions, matching funds, audited financials, or new registrations are required • Eligibility remains unclear after a focused review • A portal or compliance issue may delay submission 6. DOCUMENT AND RECORDS MANAGEMENT • Store organizational documents only in approved CYC systems. • Follow established folder structures and naming conventions. • Use clear dates, document types, client initials, program names, funders, and version numbers. • Never use meaningless file names such as “scan,” “final final,” or “document.” • Maintain version control without overwriting or deleting prior records. • Archive outdated materials rather than deleting them without authorization. • Ensure documents received through email or chat are transferred into the correct official folder. • Review files for completeness, legibility, duplication, expiration, and correct placement. • Maintain restricted permissions and minimum necessary access. • Never use public links for confidential files. • Revoke access when it is no longer required. • Conduct routine file audits and document all deficiencies and corrections. • Maintain records so they are immediately usable during funder, government, legal, program, or financial audits. 7. MEETING, BOARD, AND GOVERNANCE SUPPORT • Prepare agendas for executive, board, leadership, and major program meetings. • Assemble reports, contracts, minutes, financial information, presentations, and supporting materials. • Confirm technology, conferencing links, access permissions, and attendee availability. • Record attendance, decisions, motions, votes, action items, owners, and deadlines when assigned as note-taker. • Distribute meeting notes and create corresponding ClickUp actions promptly. • Schedule board meetings sufficiently in advance and track quorum and RSVPs. • Prepare and distribute board packets within the required timeframe. • Maintain board contact information, terms, renewals, forms, minutes, resolutions, and action logs. • Protect the confidentiality of governance records. • Track board commitments until they are completed or formally resolved. 8. COMPLIANCE, AUDIT, AND RISK SUPPORT • Read and follow CYC policies, manuals, contracts, award documents, and role-specific SOPs. • Identify requirements directly from source documents rather than relying on assumptions. • Maintain complete proof of work, submissions, communications, and approvals. • Gather contracts, client records, policies, correspondence, HR documents, grant files, and other requested records for audits or reviews. • Use checklists to confirm audit readiness and identify missing materials. • Document audit requests, findings, corrective actions, and follow-up deadlines. • Immediately escalate suspected data breaches, unauthorized access, lost files, misdirected communications, fraud, abuse, legal notices, threats, complaints, missed reporting deadlines, or safety concerns. • Do not wait for a compliance problem to resolve itself. • Do not alter, recreate, or “clean up” records after an audit or legal request has been received. • Maintain discretion and need-to-know information sharing at all times. 9. FINANCIAL AND FILING SUPPORT The Executive Assistant is not being hired as CYC’s accountant, attorney, or final compliance officer. However, you must be capable of supporting financial and filing workflows administratively. This may include: • Gathering invoices, receipts, contracts, W-9s, payment evidence, reports, and supporting records • Maintaining financial and reimbursement deadline calendars • Tracking missing documentation and outstanding responses • Preparing document packets for the CEO, accountant, funder, government agency, or tax professional • Reviewing forms and instructions for completeness • Entering approved non-decisional information into forms or portals • Tracking invoice status, reimbursement status, reporting requirements, and payment schedules • Coordinating records between the CEO, accountant, contractors, funders, and program staff • Maintaining organized grant and contract financial documentation • Supporting audit-document collection • Following up on delayed invoices or missing vendor deliverables as directed • Confirming that filing-ready packages contain the required attachments and evidence You may not independently approve expenses, execute financial transactions, change financial records, certify filings, or make accounting or legal determinations unless separately trained and explicitly authorized in writing. 10. VENDOR, PARTNER, PROGRAM, AND EVENT SUPPORT • Collect vendor W-9s, licenses, contracts, scopes of work, deliverables, and payment terms. • Create and maintain organized vendor records. • Track invoices, deliverable deadlines, missing records, and unresolved performance issues. • Coordinate partner and board availability. • Maintain professional follow-up with government agencies, funders, vendors, consultants, and community partners. • Create administrative structures for new programs, grants, pilots, and initiatives. • Upload contracts, budgets, award documents, reporting requirements, and SOPs. • Establish recurring program and reporting tasks. • Support event logistics, invitations, registration, materials, attendance records, outreach, volunteer coordination, and post-event follow-up. • Ensure new initiatives do not begin without the required documentation, ownership, deadlines, and reporting structure. DAILY OPERATING EXPECTATIONS During each scheduled workday, the Executive Assistant is expected to: • Review ClickUp, Gmail, Google Calendar, Google Drive, and urgent Google Chat communications. • Identify new, overdue, blocked, or deadline-sensitive work. • Review the CEO’s current and upcoming schedule. • Review meetings occurring within the next 48 hours. • Confirm that required invitations, reminders, agendas, links, and documents are present. • Review priority inboxes and act on routine communications. • Update active tasks with accurate status and supporting information. • Continue required client, grant, vendor, partner, and document follow-up. • Escalate risks the same day they are identified. • Close the workday with an outcome-based report. The end-of-day report must identify: • Work completed • Material progress made • Outstanding work • Blockers or risks • Required CEO decisions • Planned next actions • Links or evidence supporting completion “Done,” “all good,” “inbox checked,” or “everything completed” is not sufficient documentation by itself. WEEKLY OPERATING EXPECTATIONS Each week, the Executive Assistant will be expected to: • Provide the CEO with the upcoming meeting schedule, open time, and conflicts. • Complete the required grant research and qualification process. • Maintain the active grant and contract pipeline. • Review grant-readiness documents and flag missing or outdated materials. • Review assigned client and program workflows for unresolved steps. • Complete file and documentation quality checks. • Review outstanding partner, board, vendor, and government communications. • Update recurring deadlines and compliance requirements. • Provide a concise weekly report covering completed outcomes, unresolved items, risks, and matters requiring CEO attention. • Identify process gaps and recommend specific operational corrections. CONTINUOUS OPERATING EXPECTATIONS The following apply continuously—not only when specifically reminded: • Read the complete source document before acting. • Follow the applicable SOP and current written instruction. • Maintain confidentiality and minimum necessary access. • Protect client and organizational information. • Document work as it occurs. • Preserve evidence of submissions and communications. • Monitor deadlines and dependencies. • Follow up until the matter is resolved or formally transferred. • Escalate risk early. • Maintain accurate systems. • Protect the CEO’s time and attention. • Distinguish activity from completed output. • Never silently abandon, absorb, delay, or reassign work. • Never mark incomplete work as complete. • Never make assumptions when a contract, policy, award document, or source record can provide the answer. REQUIRED SYSTEMS Strong working proficiency is required in: • ClickUp • Google Workspace • Gmail • Google Calendar • Google Drive • Google Docs and Google Sheets • Google Meet or Zoom • Airtable • PDF and document-management tools Experience with any of the following is beneficial: • Expensify • Gusto • Bill.com • Government funding portals • Grants.gov or SAM.gov • Nonprofit CRM or case-management systems • Medicaid or government billing portals • Upwork • Canva • Electronic signature platforms SECURITY REQUIREMENTS The selected contractor must: • Sign confidentiality and data-security agreements. • Complete required onboarding and policy acknowledgments. • Use an individually assigned account and multifactor authentication. • Use a password-protected and approved device. • Maintain an updated operating system and secure internet connection. • Never use public Wi-Fi when accessing client or sensitive organizational information. • Never download CYC files to unapproved personal storage. • Never share passwords or credentials. • Report a lost device, unauthorized access, misdirected communication, or suspected breach immediately. • Return or permanently delete all CYC information at the end of the engagement as directed. WHO WILL SUCCEED IN THIS ROLE The strongest candidate will be: • A strong reader who can understand lengthy operational, grant, government, contract, and compliance documents • Highly organized without being rigid or bureaucratic • Able to move between unrelated subject areas without losing accuracy • Comfortable working directly with a Founder and CEO • Able to accept clear correction without becoming defensive • Capable of independent administrative judgment within established boundaries • Persistent with follow-up • Precise with dates, names, amounts, links, records, and attachments • Comfortable communicating with clients experiencing housing, financial, legal-system, or other instability • Respectful toward Black, Native, Latino, immigrant, disabled, low-income, and otherwise marginalized communities • Able to handle confidential information without unnecessary discussion • Skilled at identifying what is missing before declaring a task complete • Focused on reducing executive workload rather than reporting how busy they were • Willing to learn unfamiliar systems and government processes • Reliable during high-volume grant, audit, contract, or reporting periods PREFERRED EXPERIENCE Preference will be given to candidates with experience in one or more of the following: • Executive assistance to a founder, CEO, executive director, or small-business owner • Nonprofit operations • Social services, housing, behavioral health, public benefits, or human services • Grant research or grant administration • Government contracts or public-sector communications • Client intake and application support • Board administration • Compliance-document preparation • Audit readiness • Vendor and contract administration • Project or program coordination WHO SHOULD NOT APPLY Do not apply if: • You are seeking a position limited to calendar management and travel booking. • You need each written instruction repeated verbally. • You wait for reminders before beginning assigned work. • You regularly provide vague status updates without evidence. • You believe sending an email automatically completes the underlying assignment. • You are uncomfortable following detailed procedures. • You dislike documentation, file naming, or task-management systems. • You require the CEO to identify every missing step in your work. • You become defensive when errors or incomplete work are identified. • You are uncomfortable communicating with clients or handling sensitive records. • You routinely miss deadlines because you did not escalate a blocker. • You create separate systems that are not visible to the organization. • You expect to make financial, legal, policy, or executive decisions outside your authority. • You are looking for casual or inconsistent freelance work. PERFORMANCE STANDARDS Performance will be evaluated based on: • Deadlines met • Accuracy and completeness • Quality of documentation • Responsiveness during agreed working hours • Grant opportunities properly qualified and prepared • Meetings confirmed and supported • Client workflows advanced • Follow-up completed • Risks escalated early • Files and records maintained correctly • CEO workload measurably reduced • Work closed without repeated executive intervention Activity alone is not considered performance. Completed, documented, usable outcomes are the standard. APPLICATION INSTRUCTIONS Generic proposals will not be considered. Begin your proposal with the words: CYC OPERATIONAL SUPPORT Then answer each question below using numbered responses. 1. Describe the most demanding Founder, CEO, Executive Director, or senior leader you have supported. What responsibilities did you independently manage? 2. Provide an example of a multi-step assignment where you had to read source documents, identify requirements, organize the work, follow up with others, and deliver a completed result. 3. Describe your experience with nonprofit operations, social services, housing, government agencies, grants, contracts, compliance, or client administration. 4. Explain how you would determine whether a grant opportunity is genuinely eligible and appropriate before placing it on the CEO’s calendar. 5. Describe your experience handling confidential client, medical, financial, HR, legal, or organizational information. 6. Which of the required systems have you used, and what did you use each system to manage? 7. Describe a mistake you identified before it reached an executive, client, funder, or external partner. How did you identify and correct it? 8. Assume the following occur on the same day: • A funder email requires a response within 48 hours. • A client is missing a document needed for an application. • A board meeting is scheduled for the next morning without an agenda. • A grant deadline is six days away and requires a partner letter. Explain the order in which you would address these matters, what you would complete yourself, and what you would escalate. 9. State your general availability, time zone, and ability to maintain reliable overlap with Pacific Time during the agreed schedule. 10. Confirm whether you are willing to complete a paid, limited-scope skills assessment before a long-term contract is offered. HIRING PROCESS Qualified candidates may be invited to: • Complete an initial interview • Review a short sample SOP • Complete a paid operational assessment • Participate in a final interview with the Founder and CEO • Complete confidentiality, security, and onboarding requirements This is intended to become a trusted, long-term executive-operations relationship for the right person. This position is 20-25 hours a week $650-$700 a month with possibility of increase with grant & budget increase.