Controller FP&A Entrepreneurial
Trolley AI
Date: 22 hours ago
City: Vancouver, WA
Contract type: Full time
Remote
Who You'll Work With
This role reports directly to the CEO and Managing Partner and works closely with the Senior Bookkeeper to oversee the financial operations of a high-profile venture fund and its associated media projects and initiatives. You will also collaborate with fund administrators, legal teams, banking partners, and key external stakeholders to ensure the seamless financial management of our ecosystem. We are a fast-moving, dynamic startup that values collaboration, inclusion, and a strong team culture. Our team is diverse, young, and energetic, with most members in their 30s and 40s. We need someone who thrives in a startup environment, understands American business culture, and values respect, teamwork, and open communication. We are actively working to create an inclusive, non-toxic work environment and need a Financial Controller FP&A who is professional, respects all team members, and aligns with our culture of fairness, teamwork, and innovation. If you enjoy working with diverse teams, have a sense of humor, and value a collaborative, forward-thinking workplace, this is the role for you. We operate in a horizontal, collaborative organization, where all financial decisions are made by the CEO, but teamwork, transparency, and efficiency are highly valued. We appreciate direct communication and a solutions-oriented mindset. We work best with people who are proactive, clear, and constructive in their approach. If you are someone who values efficiency and respectful, open dialogue, you will thrive in this environment. You will be responsible for translating high-level financial directives from the CEO into structured processes, ensuring seamless execution by the Senior Bookkeeper and financial team.
Key Responsibilities
This role oversees financial management across all aspects of the CEOs business and personal accounts, ensuring seamless operations across multiple entities, investments, and ventures.
1. Financial Analysis & Reporting Conduct in-depth financial analysis to identify trends, forecast performance, and advise on financial strategy across multiple entities. Prepare monthly and quarterly reports for each entity, including profit & loss statements, expense summaries, cash flow updates, and customized QuickBooks dashboards. Deliver timely, accurate weekly financial updates, tracking metrics across all areas of the business.
2. Accounts Management & Cash Flow Oversee accounts payable and receivable across multiple companies, ensuring timely payments and efficient cash flow management. Monitor cash flow to ensure liquidity across global entities, adjusting forecasts as needed to align with business goals.
3. Budget Oversight & Financial Records Lead and manage the budgeting process for each entity, including variance analysis, forecasts, and scenario planning. Maintain thorough and up-to-date financial records, preparing statements that meet internal and external reporting requirements.
4. SaaS Management & Automation Manage SaaS platforms, ensuring efficient resource use, compliance, and reporting. Leverage AI-powered automation to streamline financial operations and reduce manual effort.
5. Investment & Compliance Support Evaluate investment opportunities, track portfolio performance, and ensure regulatory compliance across entities. Collaborate with fund administrators (e.g., Carta) to ensure all compliance, reporting, and financial obligations are met. Track tax obligations and ensure accurate filings, staying ahead of local and international tax regulations.
6. Payroll, Tax, and Corporate Filings Oversee payroll processing for a global team, ensuring compliance with tax laws and employment regulations in multiple jurisdictions. Manage insurance applications, ensuring adequate coverage for all entities. Handle corporate filings, tax reports, and regulatory documentation.
7. Stakeholder Reporting & Dashboard Customization: Present detailed financial reports to investors and stakeholders, highlighting key metrics and insights. Customize financial reporting dashboards to improve visibility, accessibility, and real-time data insights for key stakeholders.
8. Banking Relations & Contract Administration Act as the primary liaison for banking relationships, managing financial contracts, renewals, and service agreements. Ensure all financial systems are properly integrated with banking and accounting infrastructure.
9. Audit, Compliance, & File Management Ensure rigorous audit processes are in place, managing both internal and external audits. Maintain strict compliance with financial reporting standards, tax obligations, and regulatory requirements. Oversee file storage and document management systems, ensuring financial and legal documentation is well-organized and accessible. Work closely with fund administrator platforms (e.g., Carta) to ensure seamless financial oversight. Oversee credit line management, including establishing, monitoring, and maintaining credit facilities for multiple entities.
10. Team Leadership & Culture Alignment Lead a small team of bookkeepers, providing guidance and systems to optimize financial operations and reporting. Foster a respectful, collaborative, and inclusive financial team culture. Train and develop financial staff to ensure alignment with company values, efficiency goals, and compliance standards.
What We're Looking For
Experience: 10+ years of experience in financial management, FP&A, and multi-entity accounting. Expertise in venture capital, SaaS, and/or high-growth startup financial operations. Proven experience working with fund administrators like Carta and overseeing multi-entity financial operations.
Technical Skills: Advanced proficiency in QuickBooks Advanced/Plus, Excel, and financial management tools. Experience leveraging AI-powered automation to streamline financial processes. Proficiency in ClickUp, Slack, 1Password, and Google Drive. Strong understanding of global payroll systems, tax regulations, and legal compliance.
Soft Skills: Strong analytical and problem-solving skills, with the ability to identify financial inefficiencies and propose solutions. Highly detail-oriented, proactive, and organized, with a proven ability to manage multiple priorities. Ability to thrive in a high-growth, fast-moving startup environment while ensuring financial integrity and compliance. Effective communicator who can present complex financial data in a clear and actionable manner.
Preferred Qualifications: CPA or equivalent certification. Background in media, venture capital, or investment management. Experience building scalable financial systems and processes for high-growth companies.
What We Offer: The opportunity to lead financial strategy and operations in a fast-growing venture-backed startup. A dynamic, AI-driven environment that prioritizes efficiency, automation, and innovation. A key leadership role where you'll work directly with the CEO and Managing Partner. A remote-first work culture that values inclusivity, collaboration, and continuous learning.
Job Details Location: Remote Compensation: Competitive, based on experience
Hours: 40 hours/week
Note: We are not considering applications from agencies or recruiters at this time. Only individual candidates will be reviewed.
Submit your application here
About Us
Who We Are: Trolley is an online marketplace and platform that pairs best-in-class people with best-in-class companies. We are the future of work, create, and play, powered by our proprietary LiveWorkOS.
What We Do: Trolley builds world-class teams using best-in-class SaaS tools, AI, and project management systems. Our mission is to empower professionals with world-class training and the latest tools to work smarter, faster, and more efficiently.
Why Join Us?
This role reports directly to the CEO and Managing Partner and works closely with the Senior Bookkeeper to oversee the financial operations of a high-profile venture fund and its associated media projects and initiatives. You will also collaborate with fund administrators, legal teams, banking partners, and key external stakeholders to ensure the seamless financial management of our ecosystem. We are a fast-moving, dynamic startup that values collaboration, inclusion, and a strong team culture. Our team is diverse, young, and energetic, with most members in their 30s and 40s. We need someone who thrives in a startup environment, understands American business culture, and values respect, teamwork, and open communication. We are actively working to create an inclusive, non-toxic work environment and need a Financial Controller FP&A who is professional, respects all team members, and aligns with our culture of fairness, teamwork, and innovation. If you enjoy working with diverse teams, have a sense of humor, and value a collaborative, forward-thinking workplace, this is the role for you. We operate in a horizontal, collaborative organization, where all financial decisions are made by the CEO, but teamwork, transparency, and efficiency are highly valued. We appreciate direct communication and a solutions-oriented mindset. We work best with people who are proactive, clear, and constructive in their approach. If you are someone who values efficiency and respectful, open dialogue, you will thrive in this environment. You will be responsible for translating high-level financial directives from the CEO into structured processes, ensuring seamless execution by the Senior Bookkeeper and financial team.
Key Responsibilities
This role oversees financial management across all aspects of the CEOs business and personal accounts, ensuring seamless operations across multiple entities, investments, and ventures.
1. Financial Analysis & Reporting Conduct in-depth financial analysis to identify trends, forecast performance, and advise on financial strategy across multiple entities. Prepare monthly and quarterly reports for each entity, including profit & loss statements, expense summaries, cash flow updates, and customized QuickBooks dashboards. Deliver timely, accurate weekly financial updates, tracking metrics across all areas of the business.
2. Accounts Management & Cash Flow Oversee accounts payable and receivable across multiple companies, ensuring timely payments and efficient cash flow management. Monitor cash flow to ensure liquidity across global entities, adjusting forecasts as needed to align with business goals.
3. Budget Oversight & Financial Records Lead and manage the budgeting process for each entity, including variance analysis, forecasts, and scenario planning. Maintain thorough and up-to-date financial records, preparing statements that meet internal and external reporting requirements.
4. SaaS Management & Automation Manage SaaS platforms, ensuring efficient resource use, compliance, and reporting. Leverage AI-powered automation to streamline financial operations and reduce manual effort.
5. Investment & Compliance Support Evaluate investment opportunities, track portfolio performance, and ensure regulatory compliance across entities. Collaborate with fund administrators (e.g., Carta) to ensure all compliance, reporting, and financial obligations are met. Track tax obligations and ensure accurate filings, staying ahead of local and international tax regulations.
6. Payroll, Tax, and Corporate Filings Oversee payroll processing for a global team, ensuring compliance with tax laws and employment regulations in multiple jurisdictions. Manage insurance applications, ensuring adequate coverage for all entities. Handle corporate filings, tax reports, and regulatory documentation.
7. Stakeholder Reporting & Dashboard Customization: Present detailed financial reports to investors and stakeholders, highlighting key metrics and insights. Customize financial reporting dashboards to improve visibility, accessibility, and real-time data insights for key stakeholders.
8. Banking Relations & Contract Administration Act as the primary liaison for banking relationships, managing financial contracts, renewals, and service agreements. Ensure all financial systems are properly integrated with banking and accounting infrastructure.
9. Audit, Compliance, & File Management Ensure rigorous audit processes are in place, managing both internal and external audits. Maintain strict compliance with financial reporting standards, tax obligations, and regulatory requirements. Oversee file storage and document management systems, ensuring financial and legal documentation is well-organized and accessible. Work closely with fund administrator platforms (e.g., Carta) to ensure seamless financial oversight. Oversee credit line management, including establishing, monitoring, and maintaining credit facilities for multiple entities.
10. Team Leadership & Culture Alignment Lead a small team of bookkeepers, providing guidance and systems to optimize financial operations and reporting. Foster a respectful, collaborative, and inclusive financial team culture. Train and develop financial staff to ensure alignment with company values, efficiency goals, and compliance standards.
What We're Looking For
Experience: 10+ years of experience in financial management, FP&A, and multi-entity accounting. Expertise in venture capital, SaaS, and/or high-growth startup financial operations. Proven experience working with fund administrators like Carta and overseeing multi-entity financial operations.
Technical Skills: Advanced proficiency in QuickBooks Advanced/Plus, Excel, and financial management tools. Experience leveraging AI-powered automation to streamline financial processes. Proficiency in ClickUp, Slack, 1Password, and Google Drive. Strong understanding of global payroll systems, tax regulations, and legal compliance.
Soft Skills: Strong analytical and problem-solving skills, with the ability to identify financial inefficiencies and propose solutions. Highly detail-oriented, proactive, and organized, with a proven ability to manage multiple priorities. Ability to thrive in a high-growth, fast-moving startup environment while ensuring financial integrity and compliance. Effective communicator who can present complex financial data in a clear and actionable manner.
Preferred Qualifications: CPA or equivalent certification. Background in media, venture capital, or investment management. Experience building scalable financial systems and processes for high-growth companies.
What We Offer: The opportunity to lead financial strategy and operations in a fast-growing venture-backed startup. A dynamic, AI-driven environment that prioritizes efficiency, automation, and innovation. A key leadership role where you'll work directly with the CEO and Managing Partner. A remote-first work culture that values inclusivity, collaboration, and continuous learning.
Job Details Location: Remote Compensation: Competitive, based on experience
Hours: 40 hours/week
Note: We are not considering applications from agencies or recruiters at this time. Only individual candidates will be reviewed.
Submit your application here
About Us
Who We Are: Trolley is an online marketplace and platform that pairs best-in-class people with best-in-class companies. We are the future of work, create, and play, powered by our proprietary LiveWorkOS.
What We Do: Trolley builds world-class teams using best-in-class SaaS tools, AI, and project management systems. Our mission is to empower professionals with world-class training and the latest tools to work smarter, faster, and more efficiently.
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.
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