Chief Operating Officer

Chief Operations Officer

Job Description

Department: Operations

Level: L7 (or 8)

About the Org

Scale to Win is a fully-remote, progressive, political tech company founded in 2020 by organizing leaders from the Biden/Harris, Bernie 2020, Warren 2020, Bernie 2016, and Hillary for America Presidential campaigns. Our product offerings include Scale to Win Text, our "all-in-one" shortcode and longcode texting tool, and the Scale to Win Dialer, a predictive calling tool. Scale to Win also offers turnkey "We Text" services, where our team builds text campaigns, sends messages, collects data, and ensures compliance on behalf of clients.

We work with more than 3,000 Democratic and progressive campaigns and organizations driving change. Current and past clients include the Biden-Harris campaign, the Democratic National Committee, the Working Families Party, the AFL-CIO, UFCW, MoveOn, and For Our Future.

About the Role

The Chief Operations Officer is a strategic leader responsible for driving operational excellence, overseeing the financial health of the company, and ensuring cross-functional alignment at Scale to Win. The COO will serve as a central advisor to the Managing Partners, providing operational leadership to scale the company sustainably and setting the foundation for long-term growth. At this stage of growth, the COO will balance high-level tasks to execute the company vision while also managing day-to-day processes in finance, collection, compliance, operational systems, and more.

This leader will direct core business functions including Business Operations, People Operations, and Finance with the ultimate goal of creating efficient and scalable processes while fostering a high-performance culture and emphasizing collaboration, innovation, and continuous improvement. As a member of the

Leadership Team, they will also support the development of a mission-aligned culture.

Core Responsibilities

Operational and Financial Leadership (35%)

● Own and streamline all core operational functions, including vendor management, legal and compliance, payment processing, and internal systems

● In coordination with the Fractional CFO, lead budgeting, forecasting, and expense oversight; manage monthly close and reconcile accounts to ensure financial accuracy and risk mitigation

● Monitor company profitability and cash flow, ensuring that financial metrics align with business goals

● Oversee client invoicing and collections, monitor customer account lifecycles, and resolve outstanding or failed payments

● Collaborate on pricing strategy and ensure margin protection during contracting with vendors.

● Interface with external accountants, tax advisors, and consultants to maintain regulatory compliance and prepare for future growth

● Implement operational systems for privacy, data protection, and contract terms across products and services

Company Management and Cross-Functional Execution (30%)

● Translate strategic vision into operational plans across departments, ensuring execution against organizational goals

● Build and maintain systems for accountability across functions—partnering with leaders in Sales, Client Success, Product, and Engineering to drive results

● Serve as the internal project manager for large cross-functional initiatives, or supervise a Chief of Staff who performs this function

● Lead operational aspects of team planning and OKRs; track progress, resolve blockers, and ensure alignment with long-term objectives

● Ensure company structure and decision-making processes are scalable and support future growth

People and Team Oversight (20%)

● Manage the Operations and People teams, ensuring performance, accountability, and professional growth

● Conduct regular check-ins and feedback cycles with direct reports; support team success through coaching, mentorship, and capacity planning

● Develop internal systems to support equitable compensation frameworks, onboarding, and performance management

● Cultivate a high-trust, inclusive, and mission-driven culture across the operations function

● Model company values and support culture-building efforts across the organization

Legal, Compliance, and Business Risk Management (10%)

● Serve as the primary point of contact for external legal counsel, overseeing all legal processes including contract review, terms & conditions, and compliance with TCPA & ATDS /privacy laws

● Serve as the main point of contact for the fractional CFO, implementing and managing business policies that protect organizational risk, including margin strategy, tax exposure, and contract structure

● Navigate the tradeoffs inherent in a fast-paced, client-facing environment—balancing ideal internal systems with industry constraints

Leadership Development (5%)

● Support executive team alignment and strategic discussions related to growth, structure, and potential leadership transitions

● Build team management capacity with revenue-driven decision-making and client relationship navigation in mind

● Assess internal systems and develop a plan to support continued scale with high integrity

Candidate Profile

We are seeking a hands-on, operationally-minded leader with demonstrated experience running complex internal systems at a fast-paced organization. The ideal candidate is a systems builder who brings clarity to complexity, is energized by solving internal inefficiencies, and thrives in dynamic, evolving environments. While direct experience in the political or progressive tech space is not required, a

successful COO will be comfortable learning the industry landscape quickly and communicating confidently with stakeholders, clients, and partners.

Required Skills and Attributes

● Demonstrated experience (9+) managing financial and business operations in a high-growth or fast-moving organization

● Strong people management and leadership experience, including building teams, providing feedback, and coaching for development

● Expertise with core financial systems and compliance (e.g. invoicing, tax filing, budget forecasting)

● Skill negotiating with external vendors and managing legal and business risk

● Operational discipline, accountability, and a culture-building mindset

● Clear communication and project execution across teams

● High bias towards keeping your commitments, always ensuring follow-through.

● Flexibility; the position may evolve, and your responsibilities may shift over time.

● Comfort working in fast-paced environments and ability to navigate complex and nuanced situations.

● A creative problem-solver and self-starter. You're someone who can disagree without being disagreeable. You're comfortable coming up with new ideas and have the follow through to make those new ideas happen.

● Ability to organize and prioritize a complex work plan with ever-changing details.

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