Ceo Assistant Jobs in Silver Spring, MD (NOW HIRING)

Think of Us (TOU) is transforming the child welfare system into one where young people and families can heal, develop, and thrive. We drive purpose-driven work aligned with meaningful systems change, powered by data and the insights of lived experience. Our focus is on prevention, keeping families strong before crisis, and on building kinship-first systems so children grow up with people they know and trust. Through bold collaborations with leaders and innovators across the public and private sectors - from Presidential Administrations to local providers - we identify leverage points and co-create solutions that re-architect child welfare for the future.

Here's what this looks like:

• Built the Lived Experience Engine into the largest dataset of its kind (51,000+ voices), powering AI tools and shaping reforms
• Partnered with California to launch the Kinship Accelerator in 8 counties, backed by $150M and a budget increase from $317M $896M
• Drove a national kin-first shift: 39 states (plus 5 tribes) adopting kinship standards, unlocking $3B for families
• Operate one of the largest direct resource networks, connecting 1,827 families to $28M+ in support 

Our team members share a commitment to driving systems change through creative problem-solving, obsessive curiosity, and a love of quickly driving innovative, measurable, and impactful results. 

Department: CEO Office - CEO Office Operations 

Reports to: Chief Executive Officer 

Direct Reports: N/A

Location: Hybrid; Washington, DC (min. 3 days in the office)

Category: Full-Time, Exempt 

Think of Us is seeking an exceptional and proven Executive Assistant to provide high-level executive, operational, and relationship support to the CEO. Sixto Cancel is a visionary, energetic, and relational leader who moves quickly across multiple priorities, and this role exists to create structure, calm, and clarity around that pace and high energy without limiting his creativity or leadership style.
This is more than a scheduling role. The ideal candidate will operate as both an exceptional Executive Assistant and a trusted operational thought partner - someone who understands when to step forward, when to build structure, when to offer perspective, and when to quietly execute. The role is grounded, above all, in one responsibility: helping the CEO operate effectively.

Executive & Calendar Management

• Own and manage a highly dynamic executive calendar, coordinating internal and external meetings across multiple priorities and time zones - including regular collaboration with colleagues in Ghana and across the US.
• Anticipate scheduling conflicts, preparation needs, and follow-up actions before they become problems.
• Protect the CEO's time while maintaining appropriate accessibility to staff, board members, and external stakeholders.
• Assess which meetings require the CEO's direct involvement and which can be delegated, shortened, combined, or declined.
• Adjust quickly and calmly as priorities and plans shift throughout the day.

Meeting Preparation & Follow-Through

• Ensure the CEO is prepared for meetings, conversations, and major decisions with relevant background information, briefing materials, agendas, and participant context.
• Synthesize complex information into clear, actionable summaries the CEO can quickly absorb before high-stakes conversations.
• Help clarify the intended purpose and desired outcome of meetings in advance, flagging when an agenda is missing or unclear.
• Capture commitments, decisions, and follow-up items in real time, and track them to completion to ensure important actions do not get lost.
• Have a bias for action. Proactively follow up with the CEO or other stakeholders when action items are at risk of slipping.

Travel & Logistics

• Coordinate frequent domestic and international professional travel, including detailed itineraries, logistics, and contingency plans.
• Anticipate disruptions, preferences, and timing needs, including visa/entry and exit requirements for international travel, and remain responsive when plans change unexpectedly.
• Prepare a daily or day-ahead briefing that consolidates the CEO's schedule, key logistics, meeting prep needs, and any pending decisions or follow-ups, so he starts each day with a clear picture rather than piecing it together himself.

Thought Partnership & Prioritization

• Help translate ideas and conversations into clear, actionable next steps.
• Support the CEO in organizing his personal priorities and calendar demands, flagging what needs attention now, later, or can be delegated.
• Ask thoughtful questions that create clarity, and flag scheduling conflicts, missing follow-ups, or unresolved action items from meetings before they become urgent or critical.
• Offer perspective on how a decision or commitment might affect the CEO's schedule, bandwidth, or existing priorities, while respecting that final decisions remain with him.
• Serve as a sounding board the CEO can think out loud with, helping shape rough ideas into workable plans.

Relationship & Stakeholder Management

• Build strong working relationships with Think of Us staff, board members, funders, partners, government leaders, and external stakeholders.
• Represent the CEO and the organization with warmth, professionalism, and discretion. Confidentiality is non-negotiable.
• Maintain composure in high-pressure or ambiguous situations.
• Navigate sensitive relationships and competing requests with diplomacy, and communicate clearly with individuals at all levels.
• Extend the same respect for lived experience that guides the CEO's work to every interaction with all internal and external stakeholders.

Executive Experience & White-Glove Support

• Notice and address needs before they become requests.
• Be reachable outside standard business hours when travel disruptions, board meetings, fundraising priorities, or intense preparation for external engagements (including but not limited to policymakers and government officials) require real-time problem-solving.
• Manage the CEO's expenses, credit card reconciliation, and reimbursements with accuracy, timeliness, and financial acumen, exercising sound judgment around budget and spend.
• Create systems that reduce administrative burden and decision fatigue for the CEO.
• Maintain a high standard of service without becoming overly formal or rigid.
• Bring a sense of calm and steadiness that helps the CEO stay focused on what matters most.
• Act as a stabilizing, trusted presence - someone the CEO and organization can rely on regardless of what's happening around them.

Technology, Creativity & AI

• Use and experiment confidently with technology, including Asana and AI tools, to improve executive workflows.
• Identify opportunities to introduce automation or new systems that reduce administrative burden for the CEO.
• Support a CEO who enjoys ideating and exploring new possibilities by helping move creative ideas toward practical execution.
• Stay curious about emerging tools and approaches, bringing new ideas to the CEO rather than waiting to be asked.

We recognize that candidates may not meet every listed qualification. Research shows that individuals from underrepresented groups are more likely to opt out of applying if they don't meet 100% of the criteria. If you believe you meet many of the criteria and can succeed in this role, we encourage you to apply - we want to learn about your unique strengths and experiences.

Qualifications:

• A minimum of 5 years supporting a senior executive, with 7-8+ years desired, ideally with a founder, CEO, or entrepreneurial leader in a fast-paced, high-growth, or high-visibility environment.
• Advanced executive calendar management and complex, multi-time-zone travel coordination.
• Strong written and verbal communication skills.
• Exceptional organizational skills paired with the flexibility to adapt as priorities shift quickly as the TOU norm, attention to detail, and follow-through.
• Sound judgment, discretion, and maturity in handling confidential and sensitive matters.
• Comfort and credibility working with senior leaders, board members, and external stakeholders.
• Resilient and tough-skinned, with the ability to stay steady under pressure and receive direct feedback without taking it personally.
• Ability to prioritize under pressure and adapt quickly to changing circumstances.
• Willingness to be available outside standard business hours as needed, particularly around travel, seasons of heightened activity, or time-sensitive matters.
• Genuine interest in AI and emerging tools, with an eagerness to learn, experiment, and produce tangible and usable deliverables alongside the CEO who is deeply engaged in that space.  
• Passion for social impact, child welfare, or related mission-driven work is a strong plus.
• Resourcefulness, creative problem-solving, and the ability to work independently.
• You bring experience working with or alongside systems that impact youth and families - or you're deeply committed to learning about these systems and approaching the work with humility, curiosity, and care.
• You're motivated by impact and systems change. You thrive in a fast-growing, evolving organization and see change as an opportunity to innovate, learn, and make things better.
• You actively explore and apply AI tools to make your work more effective - using them thoughtfully to increase efficiency, improve insight, and support sound, human-centered decision-making.

The strongest candidates will be patient, trustworthy, warm, and highly organized - people who are naturally detail-oriented without becoming rigid, and nurturing without becoming parental. They will be curious, personable, and comfortable with humor and personality, while remaining calm under pressure and discreet with sensitive information. Above all, they will be self-aware enough to understand the boundaries of the role and confident enough to offer perspective within them, building trust with the CEO over time through consistency and reliability. 

• This role must be based in the Washington, DC area.
• The position follows a hybrid schedule, with most working days spent in the office.
• Significant flexibility is required based on the CEO's schedule and needs, including occasional early morning availability and, at times, evening, weekend, or travel-related support.
• The ideal candidate can pivot quickly when plans change, while also maintaining sustainable working boundaries.

What Success Looks Like
This role is successful when the CEO consistently has what he needs before he needs it - briefing materials and prep delivered ahead of meetings, travel and logistics handled without last-minute scrambles, and follow-up items tracked to completion in Asana rather than relying on memory. This frees him to focus his energy on problem-solving, relationships, creativity, and leadership rather than logistics. Success also looks like fewer preventable surprises, a calendar that reflects real priorities rather than reactive scheduling, and a CEO who can point to specific instances where the EA anticipated a need before it became a request.

At the organizational level, this role is successful when Think of Us experiences consistent, timely communication with and around the CEO's office, commitments are tracked and followed up on without dropped threads, and the CEO's office is seen internally and externally as professional, responsive, and well-run.

At TOU, we believe that taking care of our people is foundational to the impact we aim to make. Our compensation philosophy is rooted in transparency and a holistic understanding of people's needs. We believe fair, market-competitive pay is essential to attracting and retaining the exceptional talent needed to achieve our ambitious goals. As a not-for-profit organization, we design our compensation packages-including both salary and benefits-with care and in alignment with our financial sustainability. 

The annual salary for this role is $100,000-$125,000. Starting salaries for new hires will be determined based on a combination of the new hire's relevant experience and market demands.

TOU'S benefits go beyond the basics. They're designed to support your well-being, growth, and sense of purpose at work and beyond. From comprehensive health coverage to professional development support and meaningful time off, our benefits reflect our commitment to nurturing a workplace where people can thrive, both personally and professionally.

• 100% employer-paid medical, dental, and vision coverage for employees; 50% for dependents.
• Access to Talkspace for confidential therapy and mental health support.
• Short-Term Disability, Life, and AD&D Insurance included.
• Optional Long-Term Disability and Supplemental Life Insurance.
• Health Care and Dependent Care FSAs available.

• 401(k) Plan for pre-tax retirement contributions.
• Work-from-home setup stipend to optimize your workspace.

• Flexible PTO policy, plus sick leave and paid leaves of absence.
• 8 company holidays, plus two organization-wide seasonal breaks.

• TOU values continuous learning and invests in the professional development of its employees in alignment with organizational needs based on role, performance, business needs, and Company policies.
• Regular organization-wide learning sessions on relevant and reflective topics.

As part of your application,  please submit a resume outlining your skills and experiences relevant to this role.
Please note: We do not accept phone inquiries about this position in order to ensure a fair and consistent hiring process for all applicants. 

Think of Us is an Equal Opportunity Employer. We welcome and value applicants of all ...