Deputy Director, Revenue Operations

Role Overview

• 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.
• 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.
• 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.
• 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.

Requirements

• 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.

Tech Stack

• Apollo

Benefits

• 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.