Chief of Staff

Alivo•South Portland, ME

About The Position

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.

Requirements

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
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

Nice To Haves

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

Responsibilities

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.