Chief of Staff to CEO

Role Stimulus Technologies is a fast-growing, founder-led technology company with 30 years of operating history. We provide technology, cybersecurity, broadband, VoIP, and infrastructure services to businesses and communities across multiple markets. We are entering a major growth phase, including a 5,000-mile fiber expansion, capital raise activity, future acquisitions, and the continued development of a public-company-level operating model. This is not a traditional Executive Assistant role. This is a senior executive support and coordination position for someone who can operate with strong judgment, high discretion, business maturity, and the ability to represent the CEO’s priorities in meetings, projects, and follow-up. About the Role The Chief of Staff to the CEO will work directly with the CEO to manage executive communication, meeting preparation, follow-up, project coordination, vendor coordination, and cross-functional accountability. The right person will help the CEO stay focused on the highest-value priorities while ensuring that communication, decisions, action items, and strategic initiatives do not fall through the cracks. This role requires someone who is highly organized, proactive, analytical, discreet, direct, and able to operate in a fast-moving founder-led company. The Chief of Staff will not be a people manager, but will coordinate closely with leaders, vendors, project stakeholders, and internal teams to advance CEO priorities. What You Will Do Own and manage the CEO’s calendar, inbox, meeting preparation, and follow-up process. Establish and maintain a daily CEO briefing process (15 minutes or less). Lead a weekly CEO coordination meeting of 30–60 minutes to review priorities, upcoming decisions, project status, risks, communications, and follow-up items. Prepare the CEO for key meetings by organizing agendas, background information, documents, decisions needed, and expected outcomes. Attend project implementation meetings, vendor meetings, and CEO prep/debrief meetings. Attend meetings on behalf of the CEO when the CEO is traveling, unavailable, or intentionally stepping out of the meeting flow. Lead meetings when appropriate, represent the CEO’s priorities, capture decisions and action items, and brief the CEO afterward. Follow up with leaders, vendors, and stakeholders to ensure commitments are tracked and completed. Coordinate CEO-assigned projects, especially those involving implementation follow-through, process improvement, vendor coordination, leadership coordination, and cross-functional accountability. Help clarify project owners, timelines, dependencies, risks, decision points, and next steps. Improve systems for meeting notes, decision tracking, action items, project visibility, and executive follow-through. Support strategic company initiatives, including major fiber expansion activity, capital raise coordination, future acquisition preparation, process improvement, and public-company-level operating discipline. Work closely with the executive and leadership teams while remaining primarily accountable to the CEO. Protect the CEO’s time by helping determine which meetings require CEO involvement and which can be delegated, summarized, or handled through follow-up. Help train the CEO on how to work effectively with a Chief of Staff, including what to delegate, how to structure communication, and how to use the role to create leverage. What Success Looks Like Within the first 90 days, success in this role means the CEO’s calendar and inbox are under control, a daily briefing rhythm is established, a weekly coordination meeting is operating effectively, meeting notes and action items are consistently tracked, and project/vendor follow-up is more visible and organized. Over the first year, this role should materially increase the CEO’s effectiveness by improving executive communication flow, strengthening follow-through, reducing unnecessary meeting load, and supporting major strategic initiatives across the company. What We Are Looking For 7+ years of experience working directly with a CEO, founder, owner, president, or senior executive in a fast-moving organization. Experience managing executive communication, calendars, meeting preparation, meeting follow-up, project coordination, and cross-functional accountability. Strong written and verbal communication skills with a high degree of discretion and ability to handle confidential executive-level information. Ability to operate with limited direction, anticipate needs, and follow through completely. Strong organizational skills and attention to detail; ability to work with senior leaders, vendors, project stakeholders, and internal teams. Experience coordinating projects, implementations, process improvements, vendor activity, or executive initiatives. Strong technology capability and comfort with modern business systems. Experience with Microsoft 365, Teams, Outlook, Excel, PowerPoint, project management tools, documentation tools, and dashboards/reports; ability to use technology and AI tools to improve workflows and reporting. Preferred Qualifications Prior experience as a Chief of Staff, Executive Business Partner, senior Executive Assistant, operations manager, project manager, or similar executive level role. Experience working in a founder-led or owner-led company. Experience in technology-related industries (IT services, MSP, telecom, broadband, SaaS, software, cybersecurity) or technology-enabled professional services. Experience supporting capital raises, acquisitions, board/investor communications, vendor implementations, or high-growth operational initiatives. Bachelor’s degree in business, communications, management, operations, technology, or related field (preferred). High-level software implementation knowledge is a plus. The Right Fit Extremely organized and self-motivated; fast learner with strong follow-through. Direct and assertive without being aggressive; comfortable working closely with a founder/CEO. Able to handle ambiguity and communicate clearly in writing and verbally. Able to keep the CEO informed without creating extra work for the CEO. Comfortable working in a growing, evolving company with increasingly sophisticated systems. Not a fit if you need repeated direction, struggle with ambiguity, are too passive, or are uncomfortable handling sensitive executive information. Confidentiality This role requires executive-level confidentiality and discretion. The Chief of Staff will have access to sensitive C-suite information, including strategy, leadership matters, financial information, personnel issues, vendor discussions, investor and capital raise discussions, acquisition activity, legal matters, and other confidential communications. A background check and confidentiality agreement/NDA are required. Company Values Stimulus Technologies operates according to the following core values: Driven to Grow, See a Need, Fill a Need, Elevate Others, Extreme Ownership, Celebrate Success. The right candidate will demonstrate these values through judgment, communication, ownership, follow-through, and how they work with the CEO and broader team. Benefits Health insurance 401(k) Paid time off Professional growth opportunity Direct CEO exposure Involvement in major strategic company initiatives Application Requirement In addition to submitting your resume, please answer the following question in 300 words or less: How have you helped a founder/CEO reduce meeting load, improve follow-through, and stay informed without creating more work for the CEO? Applications without this response may not be considered. Stimulus Technologies is an equal opportunity employer. This job description is not intended to be an exhaustive list of all duties, responsibilities, or qualifications. Management reserves the right to amend and change responsibilities to meet business and organizational needs as necessary. #J-18808-Ljbffr