Squared Away

• Manage and optimize complex executive calendars across time zones. • Anticipate conflicts and proactively resolve scheduling issues. • Protect executive focus by enforcing priorities and boundaries. • 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. • Coordinate domestic and international travel end-to-end. • Prepare detailed itineraries and anticipate changes or disruptions. • Prepare meeting materials, agendas, presentations, and reports. • Track action items, deadlines, and follow-through across initiatives. • Create, document, and refine workflows to improve efficiency. • Identify tools and processes that reduce friction and increase clarity. • Conduct research on competitors, tools, vendors, and market trends. • Provide concise summaries to support executive decision-making. • Handle sensitive and confidential information with absolute integrity.

Role Description Squared Away is seeking a commission-based sales associate to join our Client Experience team. - Take sales calls and Zoom meetings with potential clients. - Follow the client’s preferred call style; it is at their discretion, not ours. - Maintain sales blocks Monday through Friday for at least one hour per day (e.g., two potential sales calls; calls are not guaranteed). - Take detailed sales notes and log them appropriately. - Demonstrate strong interpersonal communication skills, showing open-mindedness and curiosity across a variety of personalities. - Be comfortable taking Zoom calls with minimal distractions, a presentable background, and a professional appearance and demeanor. - Communicate company processes accurately without overpromising, while still enthusiastically selling the mission and service. - Confidently manage conversations with potential clients from initial contact through to a signed contract. - Learn and operate within HubSpot. - Understand that we will not offload a current client if you take on this role. - Communicate proactively about call conflicts within a reasonable timeframe. - Have experience in sales or customer service. - Work on a solely commission-based structure. - 15 hour plans - $37.50 - 25 & 50 hour plans - $50 - 75-hour to 125-hour plans - $62.50 - 125+ hour plans - $75 - General monthly commissions based on effort: $500–$1,000 per month - Be willing to work CST/MST/PST hours and take a call block sometime between 10:00 a.m. and 3:00 p.m. MST. - Maintain a proper space conducive to focused conversations with potential clients on Zoom. - Understand Squared Away’s policies and processes as they relate to clients working directly with assistants. - Be comfortable engaging with individuals who hold different views, and be able to speak in a neutral manner. (If not, this role is not for you.) - Embody empathy and social awareness—core pillars of the sales team’s success at our inclusive company. - Maintain professionalism and decorum across all personal social media platforms, even if profiles are private, as sales associates represent the company visually. - Stay up to date on social and political topics and understand Venture Capital and startup culture, or demonstrate a willingness to learn. - We seek to identify the best fit for the role (based on qualifications, application completion, effective use of spelling and grammar, task completion and submission, as well as how the interview goes - is it professional, are questions being answered in a complete manner, etc). Squared Away heavily focuses on the inclusion of all individuals. Qualifications - Experience in sales or customer service. - Ability to communicate effectively and professionally. - Strong interpersonal communication skills. - Comfortable with Zoom calls and maintaining a professional appearance. - Willingness to learn about social and political topics, Venture Capital, and startup culture. Requirements - Work on a solely commission-based structure. - Maintain sales blocks Monday through Friday for at least one hour per day. - Communicate proactively about call conflicts. - Be willing to work CST/MST/PST hours. - Maintain a proper space for focused conversations on Zoom. - Understand company policies and processes related to clients. Benefits - Commission-based earnings: $500–$1,000 per month based on effort. - Flexible work hours. - Opportunity to engage with a diverse range of clients.

• Take sales calls and Zoom meetings with potential clients. • Follow the client’s preferred call style; it is at their discretion, not ours. • Maintain sales blocks Monday through Friday for at least one hour per day (e.g., two potential sales calls; calls are not guaranteed). • Take detailed sales notes and log them appropriately. • Demonstrate strong interpersonal communication skills, showing open-mindedness and curiosity across a variety of personalities. • Be comfortable taking Zoom calls with minimal distractions, a presentable background, and a professional appearance and demeanor. • Communicate company processes accurately without overpromising, while still enthusiastically selling the mission and service. • Confidently manage conversations with potential clients from initial contact through to a signed contract. • Learn and operate within HubSpot. • Understand that we will not offload a current client if you take on this role. • Communicate proactively about call conflicts within a reasonable timeframe.

• Protecting client relationships and stabilizing service delivery across a contractor workforce. • Driving long-term client retention through proactive relationship management. • Serving as the primary relationship steward after onboarding, ensuring clients feel supported, heard, and confident in the partnership while identifying and resolving potential risks before they escalate. • Welcoming the client and introduce yourself as the primary Account Manager. • Offer early check-ins to establish rapport and clarify support structure. • Conduct follow-ups at key milestones to ensure satisfaction and alignment. • Maintain regular contact and relationship health monitoring. • Facilitate quarterly reviews and respond proactively to shifts in client satisfaction or flagged issues. • Follow up on survey scores and after any assistant transition to support smooth continuity.

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. Reports to: Director of Client Connections Scope: Client Experience, Retention & Relationship Health Role Summary The Account Manager is responsible for protecting client relationships, stabilizing service delivery across a contractor workforce, and driving long-term client retention through proactive relationship management. This is a client-facing role requiring the ability to communicate effectively with individuals from diverse personalities, backgrounds, and communication styles. Account Managers must approach all interactions with professionalism, emotional intelligence, and a non-judgmental mindset. The Account Manager serves as the primary relationship steward after onboarding, ensuring clients feel supported, heard, and confident in the partnership while identifying and resolving potential risks before they escalate. Application & Interview Timeline - Application Window: April 8 - April 12, 2026 at 11:59pm PT - Applications will be reviewed on a rolling basis, and interviews may begin as early as April 9, 2026 - This posting may close prior to April 12 if a strong pool of applicants is identified - Interviews may continue through April 17th, depending on applicant volume and scheduling - Anticipated start date: May 1, 2026 Eligible Work Locations This role is open to candidates who reside and are authorized to work in the following U.S. states: - Alaska - Arizona - California - Colorado - Florida - Georgia - Hawaii - Indiana - Iowa - Kansas - Kentucky - Maryland - Missouri - Nevada - North Carolina - Ohio - Oklahoma - South Carolina - Texas - Virginia - Washington What Tends to Work Well in This Role Account Managers represent the company both internally and externally and must demonstrate professionalism in communication, judgment, and conduct. - Maintaining a professional workspace that supports focused Zoom or Phone call conversations with clients. - Demonstrating a strong understanding of Squared Away’s policies and processes, particularly as they relate to clients working directly with assistants. - Being comfortable engaging with perspectives that differ from your own and communicating in a neutral, professional manner. If this is not something you are comfortable with, this role is not the right fit for you.  - Maintaining professionalism across personal social media platforms. Even when profiles are private, employees represent the brand and are expected to demonstrate professionalism and good judgment online. What You’ll Be Responsible For Account Managers serve as the primary point of contact for client conversations related to relationship health, concerns, and performance discussions. - Welcoming the client and introduce yourself as the primary Account Manager. - Offer early check-ins to establish rapport and clarify support structure. - Conduct follow-ups at key milestones to ensure satisfaction and alignment. - Maintain regular contact and relationship health monitoring. - Facilitate quarterly reviews and respond proactively to shifts in client satisfaction or flagged issues. - Follow up on survey scores and after any assistant transition to support smooth continuity. Critical Competencies Successful Account Managers demonstrate: - High emotional regulation - Strong skills in navigating difficult conversations - Excellent documentation and follow-through - Comfort operating within ambiguity - Calm, solution-oriented approach under pressure - Strong relationship-building and communication skills Discretion & Trust - Handle sensitive and confidential information with absolute integrity How We Will Support You in This Role The Account Manager role begins in a 90-day probationary period. After 90 days in the role, you will have a performance review with the Director of Client Connections. In this role, you will be supported by the Director of Client Connections and the broader Client Experience leadership team to ensure clear direction, alignment, and partnership in managing your client portfolio. You won’t be operating in a silo. We provide structured check-ins, guidance on complex client situations, and cross-functional collaboration so you are never navigating challenges alone. You will have access to established processes, documentation standards, and communication frameworks to support consistency in your work, along with visibility into client health indicators and internal updates that may impact your client portfolio. We prioritize proactive communication and cross-functional transparency, ensuring you are equipped to confidently manage relationships, identify risks early, and drive strong client outcomes. What We Expect Account Managers at Squared Away are expected to take full ownership of their client relationships, serving as the primary point of contact for client satisfaction, retention, and overall experience. This is a high-ownership role. You are trusted to proactively identify risks, address concerns with urgency and professionalism, and maintain consistent, high-quality communication that builds long-term client trust. You will collaborate closely with fellow Account Managers, the Director of Client Connections, and cross-functional teams to ensure alignment, particularly when navigating assistant performance, client concerns, or service adjustments. This role requires sound judgment, emotional intelligence, and the ability to remain calm, neutral, and solution-oriented in all client interactions, especially in high-pressure or sensitive situations. You should be comfortable operating independently while staying aligned with company standards and expectations. Strong documentation, follow-through, and attention to detail are essential.

• Manage and optimize complex executive calendars across time zones. • Anticipate conflicts and proactively resolve scheduling issues. • Protect executive focus by enforcing priorities and boundaries. • 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. • Coordinate domestic and international travel end-to-end. • Prepare detailed itineraries and anticipate changes or disruptions. • Prepare meeting materials, agendas, presentations, and reports. • Track action items, deadlines, and follow-through across initiatives. • Create, document, and refine workflows to improve efficiency. • Identify tools and processes that reduce friction and increase clarity. • Conduct research on competitors, tools, vendors, and market trends. • Provide concise summaries to support executive decision-making. • Handle sensitive and confidential information with absolute integrity.

• Manage and optimize complex executive calendars across time zones • Anticipate conflicts and proactively resolve scheduling issues • Protect executive focus by enforcing priorities and boundaries • 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 • Coordinate domestic and international travel end-to-end • Prepare detailed itineraries and anticipate changes or disruptions • Prepare meeting materials, agendas, presentations, and reports • Track action items, deadlines, and follow-through across initiatives • Create, document, and refine workflows to improve efficiency • Identify tools and processes that reduce friction and increase clarity • Conduct research on competitors, tools, vendors, and market trends • Provide concise summaries to support executive decision-making • 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 • Handle sensitive and confidential information with absolute integrity

• Manage and optimize complex executive calendars across time zones • Anticipate conflicts and proactively resolve scheduling issues • Protect executive focus by enforcing priorities and boundaries • 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 • Coordinate domestic and international travel end-to-end • Prepare detailed itineraries and anticipate changes or disruptions • Prepare meeting materials, agendas, presentations, and reports • Track action items, deadlines, and follow-through across initiatives • Create, document, and refine workflows to improve efficiency • Identify tools and processes that reduce friction and increase clarity • 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 • 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 • Handle sensitive and confidential information with absolute integrity

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 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 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 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 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.