BetterCloud
Overview
On-site role (five days per week at our HQ in Chicago, IL) reporting directly to the CEO. The Role
Crafty is seeking an Executive Assistant (EA) to support two members of our Executive Team, primarily the Chief Executive Officer (CEO) and secondarily the Chief Operating Officer (COO), and to oversee aspects of the Chicago office (approximately 25% of the role). Based out of our Chicago HQ, the EA will set the standard for proactiveness, organization and timeliness, communicating with team members across the country. The EA will collaborate with the Senior Leadership Team (SLT) and People team to align the CEO's priorities with our diverse employee base, including both exempt and non-exempt talent. We are seeking an individual who embodies our core values, is excited about an inaugural role, and desires to have significant leadership impact. Required Qualifications Project Management : Expertise in executing special projects and recurring tasks, including monthly business review (MBR) and quarterly business review (QBR) planning and logistics. Responsible for effective note-taking during meetings and ensuring leaders update their monthly goals and provide notes before scheduled meetings. Proactively addresses potential issues and develops contingency plans to mitigate disruptions and maintain smooth project execution. Communication Skills : Proficiency in drafting, sending, and managing communications, setting agendas, and preparing for meetings. Ability to convey updates and briefings clearly to stakeholders, follow up, and facilitate effective communication between team members and external contacts, including team updates, recaps, and business performance reports, as well as daily and weekly briefings for executive team members (e.g., CEO updates). Exceptionally high degree of confidentiality.
Problem-Solving Skills : Demonstrated ability to address and resolve unexpected challenges with quick problem assessment, solution evaluation, and effective fixes, showing high EQ, discretion, and adaptability in a dynamic environment. Organizational Skills :
Efficient executive calendar management and to-do lists (via Notion or another project management tool); ability to balance multiple responsibilities and meet deadlines. Precision in managing information, including expense filing and annual planning cadences, ensuring accuracy in all tasks from forwarding documents to coordinating client entertainment.
Administrative Support :
Coordinate travel arrangements, filing expenses, and managing executive team CRMs. Coordinate and execute logistics for board meetings and other key events, including managing agendas and assigning action items to stakeholders.
Office Management :
Daily restocking and maintenance of pantry and hospitality items. Organize inventory backstock in the storage room. Meeting preparation and coordination, including ordering lunch, stocking snacks, organizing cords, and ensuring meeting rooms are presentable. Safety and event management, collaborating on events such as Summer/Winter Celebrations and All Hands Meetings.
Relationship Management :
Manage internal and external relationships, set up networking opportunities, and support leadership coaching opportunities. Maintain a personal CRM (Notion) and ensure timely communication with executives' internal and external contacts.
Desired Attributes
Tools and Resources : Strong command of Gmail, Google Calendar, and Notion. Basic understanding of Slack, Lattice, Ramp, Navan, or other expense management platforms.
Business Acumen : Demonstrates understanding of company goals and strategy, providing insightful recommendations, anticipating business needs, and optimizing workflows.
Ideal Experience
At least 3 to 5 years of EA experience at a fast-paced, scaling company. Previous experience working with two leaders at once, preferably C-suite executives and/or co-founders.
Expected Results
Crafty sets goals annually, both at a team and individual level. After onboarding, you will work with your manager to establish goals for your role. The following goals are illustrative for 2025/26. Goal #1:
Weekly Operations by the end of Q2, adopt and master the standardized weekly briefing format that provides the CEO and COO with relevant updates, decisions needed, and priorities. Goal #2:
Strengthen the CEO's ability to stay organized and increase capacity by project managing priorities, inbox, travel and goals; measured through bi-annual performance reviews, ensuring you meet or exceed expectations of the role. What we offer
Our people mean everything to us. When you join Crafty, youre joining a team of passionate, smart, and supportive people who work hard and have fun along the way. We offer a compensation package including Crafty healthcare (primary health, dental, and vision), 401k, paid time off, equipment certification courses, parental leave, and Crafty-grade snacks, beverages, and events. This role also offers an opportunity to shape the future of a growing company. Creativity, ambition, and work will influence our successes. Compensation for this role is targeted at $85,000 - $100,000 per year in Chicago, IL. Final offers depend on cost of living, candidate experience, and may vary from the amounts listed above. Crafty provides equal employment opportunities (EEO) to all employees and applicants without discrimination based on race, color, religion, sex, sexual orientation, national origin, age, disability or genetics. #J-18808-Ljbffr
On-site role (five days per week at our HQ in Chicago, IL) reporting directly to the CEO. The Role
Crafty is seeking an Executive Assistant (EA) to support two members of our Executive Team, primarily the Chief Executive Officer (CEO) and secondarily the Chief Operating Officer (COO), and to oversee aspects of the Chicago office (approximately 25% of the role). Based out of our Chicago HQ, the EA will set the standard for proactiveness, organization and timeliness, communicating with team members across the country. The EA will collaborate with the Senior Leadership Team (SLT) and People team to align the CEO's priorities with our diverse employee base, including both exempt and non-exempt talent. We are seeking an individual who embodies our core values, is excited about an inaugural role, and desires to have significant leadership impact. Required Qualifications Project Management : Expertise in executing special projects and recurring tasks, including monthly business review (MBR) and quarterly business review (QBR) planning and logistics. Responsible for effective note-taking during meetings and ensuring leaders update their monthly goals and provide notes before scheduled meetings. Proactively addresses potential issues and develops contingency plans to mitigate disruptions and maintain smooth project execution. Communication Skills : Proficiency in drafting, sending, and managing communications, setting agendas, and preparing for meetings. Ability to convey updates and briefings clearly to stakeholders, follow up, and facilitate effective communication between team members and external contacts, including team updates, recaps, and business performance reports, as well as daily and weekly briefings for executive team members (e.g., CEO updates). Exceptionally high degree of confidentiality.
Problem-Solving Skills : Demonstrated ability to address and resolve unexpected challenges with quick problem assessment, solution evaluation, and effective fixes, showing high EQ, discretion, and adaptability in a dynamic environment. Organizational Skills :
Efficient executive calendar management and to-do lists (via Notion or another project management tool); ability to balance multiple responsibilities and meet deadlines. Precision in managing information, including expense filing and annual planning cadences, ensuring accuracy in all tasks from forwarding documents to coordinating client entertainment.
Administrative Support :
Coordinate travel arrangements, filing expenses, and managing executive team CRMs. Coordinate and execute logistics for board meetings and other key events, including managing agendas and assigning action items to stakeholders.
Office Management :
Daily restocking and maintenance of pantry and hospitality items. Organize inventory backstock in the storage room. Meeting preparation and coordination, including ordering lunch, stocking snacks, organizing cords, and ensuring meeting rooms are presentable. Safety and event management, collaborating on events such as Summer/Winter Celebrations and All Hands Meetings.
Relationship Management :
Manage internal and external relationships, set up networking opportunities, and support leadership coaching opportunities. Maintain a personal CRM (Notion) and ensure timely communication with executives' internal and external contacts.
Desired Attributes
Tools and Resources : Strong command of Gmail, Google Calendar, and Notion. Basic understanding of Slack, Lattice, Ramp, Navan, or other expense management platforms.
Business Acumen : Demonstrates understanding of company goals and strategy, providing insightful recommendations, anticipating business needs, and optimizing workflows.
Ideal Experience
At least 3 to 5 years of EA experience at a fast-paced, scaling company. Previous experience working with two leaders at once, preferably C-suite executives and/or co-founders.
Expected Results
Crafty sets goals annually, both at a team and individual level. After onboarding, you will work with your manager to establish goals for your role. The following goals are illustrative for 2025/26. Goal #1:
Weekly Operations by the end of Q2, adopt and master the standardized weekly briefing format that provides the CEO and COO with relevant updates, decisions needed, and priorities. Goal #2:
Strengthen the CEO's ability to stay organized and increase capacity by project managing priorities, inbox, travel and goals; measured through bi-annual performance reviews, ensuring you meet or exceed expectations of the role. What we offer
Our people mean everything to us. When you join Crafty, youre joining a team of passionate, smart, and supportive people who work hard and have fun along the way. We offer a compensation package including Crafty healthcare (primary health, dental, and vision), 401k, paid time off, equipment certification courses, parental leave, and Crafty-grade snacks, beverages, and events. This role also offers an opportunity to shape the future of a growing company. Creativity, ambition, and work will influence our successes. Compensation for this role is targeted at $85,000 - $100,000 per year in Chicago, IL. Final offers depend on cost of living, candidate experience, and may vary from the amounts listed above. Crafty provides equal employment opportunities (EEO) to all employees and applicants without discrimination based on race, color, religion, sex, sexual orientation, national origin, age, disability or genetics. #J-18808-Ljbffr