Head of Staff to the VP of Operations

Position Overview

This role reports directly to the VP of Operations and is perfect for someone who:

Wants to learn how to run and scale a company from the inside Is equally comfortable creating dashboards and designing new workflows Thrives in ambiguity and loves solving messy, cross-functional problems

• You’ll touch everything from system design (HubSpot, Looker) to forecasting and financial modeling, process improvement, and cross-team project execution.

What you'll learn

An important part of our culture is continuing education and the sharing of ideas. We offer:

A large network of investors and advisors for you to access that will help your team succeed Mentorship from executives with decades of experience in adtech and media Regular internal knowledge-sharing sessions Education budget to accelerate your team’s development

Specifically, in this role, you will learn:

How to work closely with executives who are actively scaling a venture-backed company How cross-functional strategy, planning, and leadership conversations shape decisions and drive growth How to architect, automate, and manage a CRM to align revenue, marketing, and operational goals How to think strategically and financially by supporting budgeting, forecasting, and operational modeling How to operate cross-functionally and take full ownership of projects from concept to completion Core Responsibilities Operate as the VP of Operations’ right hand, managing initiatives and ensuring accountability across departments Build, maintain, and optimize our HubSpot CRM — permissioning, automation, and reporting Design dashboards that connect sales, finance, and operations data for visibility and insight Lead projects from idea to delivery — ensuring outcomes are clear, tracked, and achieved Analyze trends in revenue, forecasting, and productivity; recommend improvements Create and maintain business documentation, playbooks, and process maps Collaborate on Finance, Legal, and HR projects as needed — from budgeting cycles to contract workflows What you'll bring 3–5 years of experience in business operations, strategy, or an analytical role Bachelor’s Degree in Business, Finance, Economics, or related field Strong HubSpot CRM knowledge (setup, automation, reporting) Proficiency with Google Sheets/Excel and comfort with data analysis Exceptional organization, communication, and problem-solving skills A bias toward ownership — you don’t wait for direction; you find the next problem to solve What will set you apart Experience in adtech, SaaS, or high-growth startups Comfort using AI tools (e.g., ChatGPT, Claude) to automate and accelerate work Interest in strategic planning, financial modeling, and process architecture A mindset that blends curiosity, ambition, and humility — you’re building your career while helping scale ours

Benefits Health & Wellness Medical, dental, and vision insurance Paid time off Parental leave Wellness & Development Stipend Holiday break Volunteer time off Financial & Compensation Competitive salary Performance-based quarterly bonus Stock options 401k Retirement Plan Workplace & Equipment Remote-first environment New York office Access to WeWork spaces available

Equal Employment Opportunity (EEO) Statement Adelaide is proud to be an Equal Opportunity Employer, committed to fostering a diverse, equitable, and inclusive workplace where all employees can thrive. We consider all qualified applicants for employment without regard to race, color, religion, sex, sexual orientation, gender identity, national origin, age, disability, veteran status, or any other legally protected status.

Our commitment to equal opportunity employment extends beyond basic compliance to encompass the active cultivation of a workplace that values different perspectives, backgrounds, and experiences.