Job Description
Job Details
Title: FP&A & Strategy Consultant – 90-Day Restructuring Engagement
Duration: 90 days
Time Commitment: 10–15 hours/week (heavier during discovery + board prep weeks)
Reports to: CEO (Project Lead)
Works closely with: Producer and Project Manager (Project/Client Lead)
PLEASE READ BEFORE APPLYING
We are only reviewing candidates who submit their application through this link: https://forms.clickup.com/9017XXXXXX/f/8cqbk2w-94437/AIXSRQTXKJKZLILBNJ
Applications submitted elsewhere will not be considered.
Overview
Were in a 90-day restructuring and strategy engagement with a consumer brand operating across content, commerce, retail, and partnerships. The business is ~120 people, currently overweight payroll vs revenue, and under pressure to deliver a clear, board-ready Option 1 plan (no recap / cap table changes in this phase).
This consultant is the analytical and structural backbone of the engagement—owning modeling, org design analysis, and board-ready strategy materials. The work is fast, ambiguous, and high-stakes; you will turn messy inputs into clean outputs the leadership team can use to make decisions.
Purpose of the Role
Own the structuring, modeling, and synthesis for this 90-day engagement.
Convert fast-moving strategy discussions into decision-ready models, org scenarios, and decks.
Reduce cognitive load on the CEO and Producer so they can focus on alignment, politics, and executive decision-making.
Produce a clean, board-ready Option 1 narrative and supporting analytics that show:
Where we are vs where were going (org + cost)
Trade-offs (headcount, payroll %, growth path)
A credible path to improve payroll efficiency (e.g., ~30% ~20% of revenue) and support long-term growth (e.g., ~$50M $200M+ over time)
Core Responsibilities
What This Role Owns
1. Org Design & Operating Model Analysis
Build current-state org view: functions, reporting lines, spans of control, headcount by vertical and shared services.
Map payroll costs by vertical (e.g., product lines / channels) and shared services (marketing, creative, ops, tech, finance, legal, supply chain).
Identify duplication, bottlenecks, over/under-staffing, and founder-dependencies.
Design 1–2 future-state org scenarios (verticals + shared services) with:
Headcount and payroll implications
Pros/cons, complexity, and execution risks
Clear decision-rights recommendations
2. Revenue & Scenario Modeling
Build and maintain a simple, transparent model distinguishing:
Audience / top-of-funnel surfaces (content, email, social, podcast)
Revenue lines (commerce/product, retail, partnerships/events, podcast monetization, advisory/equity where relevant)
Create 2–3 scenarios (e.g., maintain / rationalize & focus / growth-led) showing:
Revenue trajectory by line
Payroll and cost structure by vertical/shared services
Payroll % of revenue trend toward target
Produce decision outputs (1–2 pages, charts, and answerable questions), e.g.:
What headcount changes get payroll to target without breaking growth?
What volume of initiatives justifies in-house teams vs agency?
3. Master Strategy Deck
Own drafting and iteration of the board-ready strategy deck (Option 1 only).
Make the audience vs revenue distinction vivid and actionable for board-level readers.
Translate next-gen org framing into a clear structure:
Distribution & community
Taste & authority
Systems & leverage (AI/automation/shared services)
4. Structuring the Work
Join key calls and convert conversations into:
Decision logs + clear next steps
Workplans (owners, timelines, dependencies)
Clean document architecture (models, deck, appendices)
Keep materials aligned to constraints: payroll targets, timeline, and board expectations.
Collaboration Model
With CEO (Project Lead)
Co-build narrative and decision framing; CEO holds final call on deck direction and external messaging.
With Producer + Project Manager
Align on sequencing, deliverables, and meeting-driven deadlines; package outputs for executive/board audiences.
Explicitly Out of Scope
People management or acting as an interim executive
Running hiring processes (you may inform role design analytically)
Running financing processes or investor negotiations
Internal company finance/ops cleanup unrelated to this project
About Us
Who We Are
Trolley is a fast-growing creative operations company delivering high-impact digital and marketing solutions. We collaborate with high-profile clients to strategize, produce, and optimize compelling content that drives engagement, brand visibility, and business growth. Our creative team functions as a fully integrated powerhouse—combining strategy, design, production, and performance analysis to deliver world-class results.
AI Mindset & Continuous Innovation
We operate with an AI-first mindset and look for people who use technology to work faster, smarter, and more creatively. At Trolley, AI is part of everyday work, and we expect new hires to support a culture of curiosity, experimentation, and continuous improvement.
We Operate Under Founder Mode
Trolley operates on a Founder Mode mindset—focused on ownership, strategic thinking, and fast execution. We seek proactive, entrepreneurial thinkers who use AI to optimize work. Founder Mode emphasizes high-trust, collaborative teams where contribution outweighs control. We value creativity, resourcefulness, and clear communication. If you're impact-driven, thrive in dynamic environments, and believe in scaling through systems, this is the place for you.
Why Join Us?
Work with the Best: We recruit globally to connect top talent with forward-thinking companies.
Tech-Driven Efficiency: Leverage the latest AI and tools to amplify your impact.
Human-Centric Approach: Our systems are designed to support and elevate people, not replace them.
Training for Success: We provide world-class training to ensure you excel in every aspect of your role.
Be Part of the Future of Work
Trolley is now accepting applications from ambitious professionals who want to work at the intersection of technology and creativity. Join us in shaping the next era of work.
Title: FP&A & Strategy Consultant – 90-Day Restructuring Engagement
Duration: 90 days
Time Commitment: 10–15 hours/week (heavier during discovery + board prep weeks)
Reports to: CEO (Project Lead)
Works closely with: Producer and Project Manager (Project/Client Lead)
PLEASE READ BEFORE APPLYING
We are only reviewing candidates who submit their application through this link: https://forms.clickup.com/9017XXXXXX/f/8cqbk2w-94437/AIXSRQTXKJKZLILBNJ
Applications submitted elsewhere will not be considered.
Overview
Were in a 90-day restructuring and strategy engagement with a consumer brand operating across content, commerce, retail, and partnerships. The business is ~120 people, currently overweight payroll vs revenue, and under pressure to deliver a clear, board-ready Option 1 plan (no recap / cap table changes in this phase).
This consultant is the analytical and structural backbone of the engagement—owning modeling, org design analysis, and board-ready strategy materials. The work is fast, ambiguous, and high-stakes; you will turn messy inputs into clean outputs the leadership team can use to make decisions.
Purpose of the Role
Own the structuring, modeling, and synthesis for this 90-day engagement.
Convert fast-moving strategy discussions into decision-ready models, org scenarios, and decks.
Reduce cognitive load on the CEO and Producer so they can focus on alignment, politics, and executive decision-making.
Produce a clean, board-ready Option 1 narrative and supporting analytics that show:
Where we are vs where were going (org + cost)
Trade-offs (headcount, payroll %, growth path)
A credible path to improve payroll efficiency (e.g., ~30% ~20% of revenue) and support long-term growth (e.g., ~$50M $200M+ over time)
Core Responsibilities
What This Role Owns
1. Org Design & Operating Model Analysis
Build current-state org view: functions, reporting lines, spans of control, headcount by vertical and shared services.
Map payroll costs by vertical (e.g., product lines / channels) and shared services (marketing, creative, ops, tech, finance, legal, supply chain).
Identify duplication, bottlenecks, over/under-staffing, and founder-dependencies.
Design 1–2 future-state org scenarios (verticals + shared services) with:
Headcount and payroll implications
Pros/cons, complexity, and execution risks
Clear decision-rights recommendations
2. Revenue & Scenario Modeling
Build and maintain a simple, transparent model distinguishing:
Audience / top-of-funnel surfaces (content, email, social, podcast)
Revenue lines (commerce/product, retail, partnerships/events, podcast monetization, advisory/equity where relevant)
Create 2–3 scenarios (e.g., maintain / rationalize & focus / growth-led) showing:
Revenue trajectory by line
Payroll and cost structure by vertical/shared services
Payroll % of revenue trend toward target
Produce decision outputs (1–2 pages, charts, and answerable questions), e.g.:
What headcount changes get payroll to target without breaking growth?
What volume of initiatives justifies in-house teams vs agency?
3. Master Strategy Deck
Own drafting and iteration of the board-ready strategy deck (Option 1 only).
Make the audience vs revenue distinction vivid and actionable for board-level readers.
Translate next-gen org framing into a clear structure:
Distribution & community
Taste & authority
Systems & leverage (AI/automation/shared services)
4. Structuring the Work
Join key calls and convert conversations into:
Decision logs + clear next steps
Workplans (owners, timelines, dependencies)
Clean document architecture (models, deck, appendices)
Keep materials aligned to constraints: payroll targets, timeline, and board expectations.
Collaboration Model
With CEO (Project Lead)
Co-build narrative and decision framing; CEO holds final call on deck direction and external messaging.
With Producer + Project Manager
Align on sequencing, deliverables, and meeting-driven deadlines; package outputs for executive/board audiences.
Explicitly Out of Scope
People management or acting as an interim executive
Running hiring processes (you may inform role design analytically)
Running financing processes or investor negotiations
Internal company finance/ops cleanup unrelated to this project
About Us
Who We Are
Trolley is a fast-growing creative operations company delivering high-impact digital and marketing solutions. We collaborate with high-profile clients to strategize, produce, and optimize compelling content that drives engagement, brand visibility, and business growth. Our creative team functions as a fully integrated powerhouse—combining strategy, design, production, and performance analysis to deliver world-class results.
AI Mindset & Continuous Innovation
We operate with an AI-first mindset and look for people who use technology to work faster, smarter, and more creatively. At Trolley, AI is part of everyday work, and we expect new hires to support a culture of curiosity, experimentation, and continuous improvement.
We Operate Under Founder Mode
Trolley operates on a Founder Mode mindset—focused on ownership, strategic thinking, and fast execution. We seek proactive, entrepreneurial thinkers who use AI to optimize work. Founder Mode emphasizes high-trust, collaborative teams where contribution outweighs control. We value creativity, resourcefulness, and clear communication. If you're impact-driven, thrive in dynamic environments, and believe in scaling through systems, this is the place for you.
Why Join Us?
Work with the Best: We recruit globally to connect top talent with forward-thinking companies.
Tech-Driven Efficiency: Leverage the latest AI and tools to amplify your impact.
Human-Centric Approach: Our systems are designed to support and elevate people, not replace them.
Training for Success: We provide world-class training to ensure you excel in every aspect of your role.
Be Part of the Future of Work
Trolley is now accepting applications from ambitious professionals who want to work at the intersection of technology and creativity. Join us in shaping the next era of work.
💡 Quick Summary
Seeking a career-building opportunity? The FP&A Strategy Consultant Role position is now open for candidates interested in the Event Management Jobs sector. This role in Toronto offers a professional environment and growth potential.
Requirement Snapshot: Candidates should possess basic communication skills, a proactive attitude, and the ability to work in a team. Experience in Event Management Jobs is a plus.