About Scale to Win

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

We are seeking a high-impact Business Strategy & Operations Lead to help drive Scale to Win’s most critical, cross-functional initiatives. This is a pivotal role for an analytical and execution-oriented operator who thrives at the intersection of corporate strategy, commercial expansion, and business performance governance.

As a trusted advisor to the COO and executive leadership team, you will operate as a deployable problem-solver, bringing structure to ambiguity across multiple domains. The Business Strategy & Operations Lead looks across the entire corporate landscape—evaluating new market entry, optimizing pricing structures, managing critical vendor ecosystems, and serving as the operational liaison to legal and compliance. This role is ideal for a strategic thinker who excels at driving clarity, velocity, and alignment in a fast-paced environment.

Core Responsibilities

Strategy & Market Expansion (30%)

• Conduct strategic analyses to evaluate and help execute entry into new geographic markets, verticals, or product segments.

• Conduct strategic analyses to determine trends and identify opportunities for process and strategy improvement.

• Partner with leadership to model, evaluate, and optimize pricing strategies and commercial structures that maximize business value.

• Analyze company-wide business performance metrics to diagnose operational friction and present executive-level strategic recommendations.

• Partner with the data team to define, validate, and track core business performance metrics, ensuring executive-level reporting is accurate, trustworthy, and actionable for strategic decision-making.

• Serve as a deployable strategic operator—step into ambiguous or high-stakes situations, diagnose root causes, and design clear execution plans regardless of function.

Project Management & Corporate Governance (40%)

• Execute high-priority initiatives from inception to completion, (e.g., product launches, corporate scaling frameworks) ensuring delivery against key milestones.

• Design and manage the systems used to evaluate company performance against corporate goals; partner with the data team and key operational stakeholders to build comprehensive dashboards, refine success metrics, audit data accuracy, and run executive cadences where these insights are translated into resource allocation and strategic action.

Operational Improvement (30%)

• Build high-level operational infrastructure, cross-departmental playbooks, and business performance dashboards that enable sustainable corporate growth.

• Directionally align and collaborate with cross departmental stakeholders to synthesize core business metrics, ensuring unified data definitions for business performance tracking.

Other Duties as Needed

Other Duties as Needed: This role description is intended to convey information essential to understanding the scope of the position and is not an exhaustive list of skills, efforts, duties, responsibilities, or working conditions associated with it. Other duties may be assigned as needed to support the success of the team and organization.

Skills and Qualifications

• Typically demonstrated by 5+ years of experience navigating business operations, strategy, or cross-functional execution in fast-paced, complex, or high-growth environments.

• A proven ability to process complex, ambiguous business problems, apply logical frameworks, and translate them into clear, actionable, and scalable operational plans.

• A track record of successfully guiding cross-functional initiatives from concept to delivery. You are a systems builder who is energized by seeing the real-world, long-term impact of your strategic work.

• Comfort managing expansive ownership across distinct business domains, with strong self-direction and prioritization skills to navigate frequent context switching.

• Exceptional emotional intelligence and relationship-building skills. You naturally establish trust, create alignment, and drive velocity across various departments without relying on top-down authority.

• Strong capability in analyzing data to derive insights; highly comfortable modeling business outcomes, pricing frameworks, or performance metrics using Excel or similar analytical tools.

• Proven experience defining reporting requirements and building dashboards (using BI tools or advanced spreadsheets) to monitor business performance, translate data trends into a cohesive narrative, and isolate areas for operational improvement.

• A builder mindset with an eagerness to design processes from the ground up and the comfort to pivot quickly based on evolving business needs.

• Deep motivation by our company’s mission and genuine excitement about the opportunity to combine personal and professional interests.

Nice to have:

• Technical proficiency in querying databases (e.g., SQL).

• General user-level familiarity with CRM platforms or GTM tech stacks (e.g., HubSpot).

Salary and Benefits

• $145,000 yearly salary (base). As part of our commitment to equity, salaries are non-negotiable.

• This role may be eligible for a discretionary bonus as determined by the company in its sole discretion.

• 401k matching up to 6% after a provisional period.

• Ten paid company holidays, two floating holidays, and a week and a half-long holiday break at the end of the year.

• Generous paid vacation (up to 24 days a year with time accrued monthly); paid sick leave; paid short-term medical, caregiver, bereavement, and other personal leave.

• 16 weeks of paid parental leave and an additional 4 weeks of part-time, fully-paid flex time. This is available to all new parents of any gender, including adoptive parents.

• Fully-paid premium, $0 deductible, top-notch medical insurance, as well as dental and vision insurance, for you and your dependents.

• Remote working with flexible working conditions, a stipend to support your home office setup, and access to a company computer.

• Every employee is invited to donate 25,000 free texts to a non-profit of their choice each year.

• To support continued professional growth and development, Scale to Win offers each employee an annual $2,000.00 stipend towards achieving your professional development goals.

Travel Expectations

We are a remote-first team that gathers in person a couple of times a year for team building and alignment. This role requires roughly 10% travel, primarily for offsites and critical external meetings with partners or customers.

Secure Handling of Sensitive Data

This role may frequently handle sensitive company and personal data. Given this, staff must ensure all financial, billing, and sensitive vendor or customer data is processed in a private, distraction-free environment to maintain high accuracy and security. To protect the Company’s intangible assets and PII, this work must not be performed in public or unsecured settings in accordance with all company data access policies and applicable laws.

Interview Process + Timeline

• Submit resume and application

• Round 1 - Screen Interview

• Round 2 - Hiring Manager Interview

• Round 3 - Hiring Exercise + Panel Interview/ Exercise Probe

• Round 4 - Co-CEO Interview

• Reference Checks

The position will be open until filled, and applications will be reviewed on a rolling basis.

Applicants must be currently authorized to work in the United States on a full-time basis. At this time, we’re unable to sponsor or take over sponsorship of employment visas.

Interview Accommodations

Scale to Win is committed to providing all candidates a respectful and inclusive interview process. If you require any accommodations to fully participate in the interview process—such as alternative formats, extended time, assistive technology, or other support—please let us know. You can request accommodations by emailing peopleops@scaletowin.com.

Scale to Win is an equal opportunity employer. In keeping with our beliefs and goals, no applicant will face discrimination or harassment based on race, color, ancestry, national origin, religion, age, gender, marital domestic partner status, sexual orientation, gender identity, disability status, or veteran status. Above and beyond discrimination/harassment based on “protected categories,” Scale to Win also strives to prevent other, subtler forms of inappropriate behavior (e.g., stereotyping) from ever gaining a foothold. Whether blatant or hidden, barriers to success have no place at Scale to Win.