Deputy Director, Revenue Operations

Deputy Director, Revenue Operations

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

The Revenue Operations Manager plays a critical and foundational role at Scale to Win, serving as the architect of our go-to-market systems and the connective tissue between our Sales, Client Success, and Marketing teams. This is not a role for a casual HubSpot user — it is a role for a builder, a fixer, and a systems thinker who thrives on turning operational chaos into clean, scalable infrastructure.

In this role, you will own Scale to Win's HubSpot ecosystem end-to-end: auditing and rebuilding what exists, designing new workflows and pipelines, and ensuring that the data flowing through our CRM is accurate, trustworthy, and actionable. You will partner closely with senior leadership to translate strategic goals into functional technical systems, build the reporting infrastructure that GTM leaders rely on to make decisions, and create the documentation and training that ensures our team actually uses the tools we build. This is a Deputy Director-level individual contributor role with significant organizational influence, reporting to the Vice President of Sales.

Core Responsibilities

HubSpot Systems Architecture & Administration (40%)

• Serve as the primary HubSpot administrator, owning all CRM architecture including objects, workflows, properties, pipelines, and permissions across Sales Hub and Service Hub
• Audit the existing HubSpot environment, identify legacy technical debt and misconfigured processes left by prior consultants, and develop and execute a structured remediation plan
• Design and build scalable, well-documented workflows that map complex business processes without creating clutter or creating systems only you can understand
• Manage user permissions, data validation rules, and governance standards that keep the CRM clean and trustworthy at scale

Data Integrity & Revenue Reporting (25%)

• Establish and maintain a single source of truth for STW's revenue data, including ARR, GRR, NRR, churn, renewal rates, and sales velocity
• Build and maintain dashboards that GTM leaders, including Sales, Client Success, and Finance, actively use to make decisions
• Identify and resolve data quality issues, tracing anomalies back to their source and implementing preventative checks to stop them from recurring
• Partner with Finance Leadership to ensure HubSpot data accurately reflects billing and subscription data

Cross-Functional Systems Integration (20%)

• Own the integration and data flow between HubSpot and STW's broader GTM tool stack, including (but not limited to) Slack, Apollo, PandaDoc, Zoom Revenue Accelerator, and LinkedIn Sales Navigator
• Serve as the operational translator between senior leadership's strategic goals and the technical systems required to achieve them
• Proactively identify gaps in current tooling and propose solutions that will serve STW as it scales

Training, Adoption & Documentation (15%)

• Develop and maintain a Scale to Win RevOps Playbook that documents all CRM processes, workflows, and standards in plain language that the full team can follow
• Lead training and change management efforts to drive team adoption of new and improved systems
• Serve as the go-to internal resource for CRM questions, troubleshooting, and process guidance across Sales and Client Success

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

Must-Haves

• 4-5 years of experience in Revenue Operations or Sales Operations, ideally within a high-growth B2B SaaS environment
• Strong commitment to progressive values and genuine alignment with Scale to Win's mission to help Democratic and progressive campaigns and organizations win
• Demonstrated experience as a primary HubSpot administrator, not just a user, with hands-on ownership of CRM architecture, workflows, objects, and properties in HubSpot Sales Hub and/or Service Hub
• Current HubSpot Administrator certification, or equivalent expert-level demonstrated experience
• Proven experience inheriting a messy or poorly implemented CRM environment and successfully auditing, remediating, and re-architecting it
• Experience managing the full lead-to-revenue lifecycle, including recurring revenue pipelines, renewal workflows, and Customer Success operations — not just top-of-funnel sales pipelines
• Experience building revenue dashboards that track ARR, churn, and sales velocity for GTM leadership
• Strong documentation skills and a demonstrated ability to build processes that others can understand, follow, and maintain without your involvement
• Comfort working as a hands-on individual contributor in a small, fast-moving organization where you are the team, not a member of a large specialized department

Nice-to-Haves

• SQL proficiency or other advanced data querying skills for complex reporting and data integrity work beyond standard HubSpot reporting tools
• Administration or optimization experience with secondary GTM tools in STW's stack, including Apollo, PandaDoc, or Zoom Revenue Accelerator
• Formal experience in change management, organizational enablement, or developing training programs that drive high adoption
• Experience integrating HubSpot with billing or finance systems to ensure revenue data accuracy
• Familiarity with the progressive political or nonprofit technology space

Salary and Benefits

• $110,000 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

This role may require occasional travel to support client meetings, campaign events, trainings, or company gatherings. Travel expectations will vary based on client needs and campaign cycles, particularly during peak election seasons.

How to Apply

To apply for this position, please visit https://scaletowin.com/careers and fill out the application.

Interview Process + Timeline

• Submit resume and application
• Initial interview
• 2nd interview
• 3rd interview
• Assessment
• Final 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 jobs@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.