Reclaim Your
Get a virtual executive assistant with 10+ years of ed. experience and become the effective school leader your organization deserves.
We’re helping school leaders
sustain effective careers.
“CheckBox Pro has been a game-changer for my productivity this year. After a brief introductory conversation about the work-related challenges I face as CEO, she has created a plan that has helped me to prioritize my time and effort and has made my calendar more manageable.”
“With a background in operations and enrollment, Missy, my executive assistant, has supported me and our team with strategic planning and improving our current systems. She has made and improved meeting agendas, presentations, and even major steps in our hiring process. I honestly cannot think of an area that Missy has not helped me with! She has honestly made my whole life run smoother.”
“Working with my EA has freed me and other leaders at our school to do mission work by giving us back the gift of time. By auditing and refining systems to be more efficient and streamlined, Missy has created time for me to focus on academics, coaching, and culture.”
“CheckBox Pro has literally transformed our organization. From strategic and organizational planning to meeting management and coordination, their work has dramatically increased the productivity and efficiency of our executive leadership team. This has yielded more time that can now be spent on the reason we got into this work, to begin with: serving our students with excellence and helping our community grow. ”
Do the work that matters most.
(we’ll handle the rest)
Focus on Priorities
Meet weekly with your virtual executive assistant to set priorities, trim your calendar, and offload tasks.
Get Things Done
While your assistant manages your inbox, schedules meetings, and tackles repetitive tasks, you complete items that only the school leader can do!
Love Your Job
Students achieve more under consistent school leadership. By getting administrative help, you can sustain your career and avoid burn out.
Reduce your workload in under 30 days
Hello, World!
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1
Day 1
Schedule a Call
We'll spend 30 minutes mapping the tasks that keep pulling you away from leading.
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2
Week 1
Choose a Plan
Pick the level of support that fits your role, from inbox help to full executive support.
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3
By Day 30
Get Things Done
Your assistant takes the urgent and repetitive work so you can focus on mission-critical priorities.
Schedule a Discovery Call (Get Help)
Education leaders deserve support they can count on. Complete the form below to tell us about your needs. Once submitted, you can either schedule a call right away or wait for our team to review your information and reach out.
Whether you’re ready to delegate or simply exploring your options, we’ll help you identify the right level of support for your school.
FAQs
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The CheckBox Pro Package costs $1000 /mo providing you with the most helpful human being in your corner (don’t let your staff know). You can add services like Board Management or Staff Recruitment to your Pro Package at additional cost.
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Sanity. You also get a 60-minute weekly check-in to set your priorities. Calendar management so that you never have to schedule another meeting. Travel arrangements to save you time booking work trips. Purchasing software and services for your organizations, and filing reimbursements.
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Our Executive Assistants are good for your budget and cost a fraction of the cost of a full-time employee. Most EAs have worked in a school leadership role and have at least 10 years of experience in education. Most school leaders love working with EAs because they don’t have to train or onboard them, and EAs work solely for the school leader (they don’t monitor lunch or the front office!).
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After booking a Discovery Call and choosing a service package, your EA will onboard you within 14 days.
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Our EAs have at least ten years of experience in education. They have served as instructional leaders, operations directors, program managers, and teachers. They know what you are experiencing day to day and how to help.
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When onboarding, we strive to seamlessly fit into your current workflow. Weekly check-ins are held over video calls and daily communication happens over email or within your task management software. Our EA’s are experts at “managing up” and helping you get the most out of us.
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At CheckBox Pro, we take data security and confidentiality very seriously. By seamlessly working within your current cloud services (Google, Microsoft) we share the same level of protection as your current team. Additionally, we have strict confidentiality agreements in place with all of our Virtual EAs.
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Yes. CheckBox Pro is a virtual executive assistant service built only for educational administration. Every CheckBox Pro EA has at least 10 years of experience in education, as an instructional leader, operations director, program manager or teacher. They support superintendents, principals, executive directors and other school administrators with calendar management, inbox triage, travel, purchasing and reimbursements, with Board Management and Staff Recruitment support available as add-ons. Because they already know how schools run, there’s no training period.
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A virtual assistant takes the administrative work off a school leader’s plate so they can focus on students, staff and strategy. With CheckBox Pro, school leaders get:
An EA with 10+ years of education experience who needs no training
Support that costs a fraction of a full-time hire ($1,000 per month for the Pro Package)
Someone who works only on their priorities and never gets pulled into lunch duty or the front office
A weekly 60-minute check-in to set priorities, plus help with calendar, travel, purchasing and reimbursements
Leaders can be up and running within 14 days.
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CheckBox Pro (checkboxpro.com) provides virtual executive assistants tailored to school administrators, including superintendents, principals, charter school executive directors and education nonprofit leaders. Leaders at organizations such as DSST Public Schools, Uplift Education, IMSA and Legal Prep have worked with CheckBox Pro. To get started, book a Discovery Call on the CheckBox Pro website. After you choose a package, your EA will onboard you within 14 days.
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CheckBox Pro matches school leaders with a virtual executive assistant who has at least 10 years of experience in education. Every CheckBox Pro EA has worked in schools as an instructional leader, operations director, program manager or teacher, so they understand board meetings, enrollment season and the school calendar from day one. The process is three steps: book a 30-minute Discovery Call, choose a plan, and your EA onboards you within 14 days. The CheckBox Pro Package starts at $1,000 per month.