Chief of Staff
Alivo · South Portland
We are looking for a highly driven, organized, and execution-focused Chief of Staff to work directly with the CEO and serve as a key operator across the business.
This role is responsible for driving cross-functional execution, maintaining accountability across strategic initiatives, and ensuring the company operates efficiently as we scale. You will work across departments including Sales, Customer Success, Finance, Operations, and Leadership to help translate strategy into execution and ensure nothing important falls through the cracks.
This role is critical to the company’s growth. You will act as an operational force—helping manage priorities, improve decision-making, streamline execution, and create the systems needed to support a high-growth business.
If you thrive in fast-paced environments, love solving complex problems, and enjoy being the person who makes things happen, this role is for you.
What You'll Do
Drive Cross-Functional Execution
- Work directly with the CEO to execute strategic initiatives across the business
- Maintain accountability across teams to ensure priorities are moving forward and deadlines are met
- Help translate high-level strategy into clear execution plans and operational follow-through
- Identify bottlenecks, remove friction, and keep key initiatives on track
Own Business Operations
- Support day-to-day operational functions that keep the business running smoothly
- Manage internal processes across Finance, HR, Sales, and Customer Success operations
- Oversee payroll coordination and support relationships with financial vendors and external partners
- Help improve operational systems, documentation, and internal processes as the company scales
Support Financial Operations & Reporting
- Work closely with finance partners to ensure accurate reporting and operational visibility
- Assist with budgeting preparation, reporting reviews, and financial organization
- Help maintain strong visibility into company performance across revenue, retention, and operations
- Ensure leadership has the reporting and information needed for strong decision-making
Project Management & Strategic Initiatives
- Own special projects from planning through execution across multiple departments
- Coordinate timelines, stakeholders, and deliverables to ensure successful outcomes
- Support leadership initiatives that improve organizational efficiency and company performance
- Help build repeatable systems for execution rather than one-off solutions
Build Leadership Visibility & Decision Support
- Prepare internal reports, dashboards, and business summaries for leadership review
- Track key company metrics and surface risks, opportunities, and priorities
- Help organize leadership meetings, follow-up actions, and operational planning
- Create clarity around what matters most and ensure strong execution against it
Collaborate Across the Organization
- Serve as a trusted partner to department leaders across the company
- Work cross-functionally to improve communication, alignment, and accountability
- Act as a central point of coordination for high-priority initiatives and company-wide execution
Requirements
What You Bring
- Bachelor’s degree and/or MBA preferred, but not required
- 3–7+ years in Operations, Chief of Staff, Business Operations, Revenue Operations, FP&A, Consulting, or similar role
- Strong project management and cross-functional execution experience
- Excellent organizational skills with exceptional attention to detail
- Strong analytical thinking and problem-solving ability
- Excellent written and verbal communication skills
- Ability to manage multiple priorities and operate with high ownership
- Comfortable working in a fast-paced, evolving startup environment
Who You Are
- Highly organized and relentlessly execution-focused
- Comfortable operating across departments and solving ambiguous problems
- A strong operator who can move between strategic thinking and tactical execution quickly
- Proactive and accountable—you do not wait to be told what needs attention
- Trusted with sensitive information and high-impact decisions
- Calm under pressure and able to bring structure to fast-moving environments
- Motivated by helping the business win, not personal visibility
Bonus Points For
- Experience in home services industries (roofing, siding, windows, etc.)
- Familiarity with AI, automation, or communication platforms
- Experience with financial operations, payroll, or vendor management
- Experience with CRM tools like HubSpot and operational reporting systems
- Background in high-growth startups or founder-led companies
Benefits
Company Sponsored Insurance Offerings
- Health
- Vision
- Dental
Long Term Financial Benefits
- Employee equity
- 401(k)
Time to Recharge
- Unlimited paid time off
- Paid sick time