About Squared Away Squared Away supports founders, executives, and leadership teams operating at a high level of complexity and pace. Our assistants are not task-takers. They are trusted, strategic partners who bring structure, clarity, and follow-through to demanding environments. We exist to give people their most valuable resource back: time. That work requires judgment, discretion, and consistency, every single day. Squared Away maintains a rolling application for all of our Executive Assistant position. This posting is for Q2 2026 (April - June) What We're Looking For This is not an entry-level role, and it is not a side role. As a Chief Executive Assistant at Squared Away, you will support senior executives who expect proactive thinking, excellent communication, and dependable execution. You will manage competing priorities, anticipate needs before they are voiced, and operate with a level of ownership that mirrors in-house executive support. This is an executive support role first. However, some of the executives we support operate heavily in marketing, content, and growth. We are particularly interested in candidates who bring experience or interest in marketing and can support related initiatives when needed. This role is best suited for those with exposure to marketing, content, or growth-focused environments. Not sure this is the right fit? This role is designed for candidates with experience or interest in marketing. If your background is more general, we encourage you to apply to our Chief Executive Assistant (Generalist) role. Our team reviews candidates across all tracks, so applying to the role that best reflects your experience helps us evaluate you more effectively. This is an independent contractor role designed for experienced professionals who want flexibility without sacrificing standards. What Tends to Work Well in This Role Our work is fast-paced, collaborative, and built on trust. Assistants who thrive here typically: - Have established experience supporting senior executives - Enjoy variety and problem-solving over repetitive task work - Are available and responsive during weekday business hours - Take a proactive approach and anticipate needs rather than waiting for direction - Stay effective when priorities change or when not everything is fully defined - Treat confidentiality and discretion as non-negotiable - Structure their day with dedicated work blocks in the morning and afternoon, allowing for consistent availability, focused work time, and timely communication with executives If you see yourself in this list, you’re likely a great match for how we work at Squared Away. What You’ll Be Responsible For Executive Operations & Time Management - Manage and optimize complex executive calendars across time zones - Anticipate conflicts and proactively resolve scheduling issues - Protect executive focus by enforcing priorities and boundaries Executive Communication - Manage executive inboxes with discretion and sound judgment - Draft, respond to, and triage correspondence on behalf of executives - Ensure urgent matters are surfaced promptly and appropriately Travel & Logistics - Coordinate domestic and international travel end-to-end - Prepare detailed itineraries and anticipate changes or disruptions Preparation & Execution - Prepare meeting materials, agendas, presentations, and reports - Track action items, deadlines, and follow-through across initiatives Systems & Process Improvement - Create, document, and refine workflows to improve efficiency - Identify tools and processes that reduce friction and increase clarity Research & Strategic Support - Conduct research on competitors, tools, vendors, and market trends - Provide concise summaries to support executive decision-making - Support marketing-related research, including audience insights, content trends, and competitor positioning when applicable Marketing Support (When Applicable) - Assist with content coordination, scheduling, and publishing - Support email marketing or newsletter workflows - Help organize campaign timelines and deliverables - Conduct light copy editing or drafting as needed Discretion & Trust - Handle sensitive and confidential information with absolute integrity What Success Looks Like in the First 90 Days In the first 90 days, successful Chief Executive Assistants at Squared Away typically: - Actively take on client work and build momentum by supporting assigned clients successfully - Build trust and rapport with their executive(s) through consistent communication and follow-through - Develop a strong understanding of executive priorities, preferences, and working style - Take ownership of calendar and inbox management, proactively anticipating needs and resolving issues before escalation - Establish reliable systems for tracking tasks, deadlines, and follow-ups - Communicate clearly and confidently, even when priorities shift or information is incomplete - Maintain discretion and professionalism while handling sensitive information - Structure their workday to balance availability, focused work time, and responsiveness This is not about perfection. It’s about progress, ownership, and building momentum.

About Squared Away Squared Away supports founders, executives, and leadership teams operating at a high level of complexity and pace. Our assistants are not task-takers. They are trusted, strategic partners who bring structure, clarity, and follow-through to demanding environments. We exist to give people their most valuable resource back: time. That work requires judgment, discretion, and consistency, every single day. Squared Away maintains a rolling application for all of our Executive Assistant position. This posting is for Q2 2026 (April - June) What We're Looking For This is not an entry-level role, and it is not a side role. As a Chief Executive Assistant at Squared Away, you will support senior executives who expect proactive thinking, excellent communication, and dependable execution. You will manage competing priorities, anticipate needs before they are voiced, and operate with a level of ownership that mirrors in-house executive support. This is an executive support role first. However, Some of the executives we support require additional support with financial organization and bookkeeping-related workflows. We are particularly interested in candidates who have hands-on experience with bookkeeping tasks such as expense tracking, invoice management, and reconciliation, and who are comfortable working with financial data. This role is best suited for those with experience supporting bookkeeping or financial operations in a practical, execution-focused capacity. This is not an accounting role and does not include tax preparation or advisory responsibilities. Not sure this is the right fit? This role is designed for candidates with bookkeeping experience or exposure to financial workflows. If your background is more general, we encourage you to apply to our Executive Assistant (Generalist) role. Our team reviews candidates across all tracks, so applying to the role that best reflects your experience helps us evaluate you more effectively. This is an independent contractor role designed for experienced professionals who want flexibility without sacrificing standards. What Tends to Work Well in This Role Our work is fast-paced, collaborative, and built on trust. Assistants who thrive here typically: - Have established experience supporting senior executives - Enjoy variety and problem-solving over repetitive task work - Are available and responsive during weekday business hours - Take a proactive approach and anticipate needs rather than waiting for direction - Stay effective when priorities change or when not everything is fully defined - Treat confidentiality and discretion as non-negotiable - Structure their day with dedicated work blocks in the morning and afternoon, allowing for consistent availability, focused work time, and timely communication with executives If you see yourself in this list, you’re likely a great match for how we work at Squared Away. What You’ll Be Responsible For Executive Operations & Time Management - Manage and optimize complex executive calendars across time zones - Anticipate conflicts and proactively resolve scheduling issues - Protect executive focus by enforcing priorities and boundaries Executive Communication - Manage executive inboxes with discretion and sound judgment - Draft, respond to, and triage correspondence on behalf of executives - Ensure urgent matters are surfaced promptly and appropriately Travel & Logistics - Coordinate domestic and international travel end-to-end - Prepare detailed itineraries and anticipate changes or disruptions Preparation & Execution - Prepare meeting materials, agendas, presentations, and reports - Track action items, deadlines, and follow-through across initiatives Systems & Process Improvement - Create, document, and refine workflows to improve efficiency - Identify tools and processes that reduce friction and increase clarity Research & Strategic Support - Conduct research on competitors, tools, vendors, and market trends - Provide concise summaries to support executive decision-making Financial & Bookkeeping Support (When Applicable) - Track and organize expenses, receipts, and financial records - Assist with invoice tracking and follow-ups - Support reconciliation of transactions and documentation - Prepare basic financial summaries for executive review - Coordinate with accountants, bookkeepers, or finance teams Discretion & Trust - Handle sensitive and confidential information with absolute integrity What Success Looks Like in the First 90 Days In the first 90 days, successful Chief Executive Assistants at Squared Away typically: - Actively take on client work and build momentum by supporting assigned clients successfully - Build trust and rapport with their executive(s) through consistent communication and follow-through - Develop a strong understanding of executive priorities, preferences, and working style - Take ownership of calendar and inbox management, proactively anticipating needs and resolving issues before escalation - Establish reliable systems for tracking tasks, deadlines, and follow-ups - Communicate clearly and confidently, even when priorities shift or information is incomplete - Maintain discretion and professionalism while handling sensitive information - Structure their workday to balance availability, focused work time, and responsiveness This is not about perfection. It’s about progress, ownership, and building momentum.

Role Description The Senior Executive Assistant is responsible for the day-to-day administrative operational activities of the Chief Executive Officer with additional responsibilities managing events and projects for various executive team members. Reporting to the Chief Executive Officer, the Sr. Executive Assistant is an expert multi-tasker who is adept at handling complex tasks in a fast-paced virtual environment. You will be working 100% remotely. What You’ll Be Doing: - Coordination of executive and company travel needs to include flight and lodging arrangements, vendor coordination, expense and budget tracking, agenda and meeting content support, and various other “off-site” needs. - Responsible for spend management for CEO to include expense tracking, vendor spend tracking and cost optimization for larger, coordinated expenses. - Coordination of customer correspondence and communication in partnership with our Executive Team members (examples of this are fielding/routing customer emails and phone calls, diligent and timely customer follow up, and interaction with our Customer/Partner Advisory Council). - Responsible for operational and administrative support for the CEO, on the day-to-day operations of the business (examples include calendar management, meeting minutes and follow up, outside vendor correspondence, reporting, board of director correspondence, and more). - Manage and report on Key Performance Indicators for the business. - Gather and format data for weekly, monthly, and/or quarterly scorecards. - Report departmental data as needed to our investors. - Observe, review and analyze processes to identify inefficiencies and areas where improvements can be made, and make appropriate recommendations. - Special projects as needed or assigned; travel occasional/minimal. Qualifications - 10+ years of experience supporting the CEO, President and other C-level executives. - Experience working in a software or high-tech company. - Experience managing complex travel, organizing company meetings and events, and managing budgets. - Must have experience working in a remote environment. - Must have the ability to anticipate needs, staying 3 steps ahead at all times, while taking initiative in a fast-paced environment. - Above average administrative technical skills with a deep understanding of business tools to include, but is not limited to, the following: G-Suite, Slack, Calendar integration, MS Office, AI Tools (Claude, Gemini, ChatGPT). - Excellent time management, prioritization, and organizational skills. - Experience managing logistics, tracking projects and collaborating with multiple teams and leaders. - Must have flexibility to respond after normal business hours. - Must be located in eastern time zone. - Direct and decisive communication style, both oral and written. - Proven ability to operate with discretion and handle confidential information. - Ability to successfully navigate ambiguity in a fully remote environment. Requirements - Preliminary Zoom Screen w/ HR, 30m. - Interview with Chief People Officer, 1 hour. - Interview with CEO, 45m. - eTeam Interview, 45m (x2). - Live, in-person interview is a required final step before an offer is extended. - All successful candidates will undergo a thorough background and identity screening during the onboarding process. Benefits - Pay Range: $124,000 - $165,000 (based on experience, targeting $150,000). - Remote first: We are the PIONEERS of “work from home” - remote work is all we have ever done and we do it well! - Equity Appreciation Program: Syncro offers an equity program that everyone participates in. - Unlimited PTO: With a 2 week annual minimum, Syncro wants you to take time when you need it. - 401k Plan: A hassle-free plan with a 2.5% company match of your annual salary. - Health Insurance: Syncro covers 95% of the monthly premiums for you and your dependents. - Parental Leave: Up to 6 weeks paid parental leave. - And more!: Ask us about our other benefits like Pet Insurance, Flexible Spending Accounts, 100% employer paid Short Term Disability, and Ultra-Remote Work.

Participate in stock-related duties such as retrieving and circulating items. Help maintain and care for our equipment and devices as needed.