Revenue Operations & Sales Enablement Specialist
When
When Revenue Operations & Sales Enablement Specialist Remote · Full time
Revenue Operations & Sales Enablement Specialist
About When
Description
About When
When is a venture-backed, US-based technology company transforming the way companies offboard employees. Our AI-powered health insurance marketplace and post-employment platform help employers reduce COBRA costs and support employees through career transitions. We're solving a critical gap in the employee lifecycle with innovative tech and a people-first approach.
The Opportunity
We're looking for a Revenue Operations & Sales Enablement Specialist to help implement the systems, processes, and programs that will enable our sales team to scale. This is a hands-on execution role where you'll bring structure and operational rigor to a growing sales organization.
You'll work directly with a fractional GTM executive and the broader executive team who will provide strategic direction and guidance. Your job is to take that strategy and make it real—configuring HubSpot, building out training materials, creating reports, and keeping our sales operations running smoothly.
This role is ideal for someone who's a strong executor, enjoys operational work, and wants to learn from experienced GTM leadership while making a tangible impact at a fast-growing startup.
What You'll Do
Execute Revenue Operations Tasks
- Configure and maintain HubSpot CRM—pipeline stages, deal workflows, and automation
- Build and update dashboards and reports to track pipeline health, conversion rates, and sales activity
- Support forecasting by pulling data and maintaining accurate pipeline records
- Maintain data hygiene—clean up duplicates, ensure fields are populated, enforce CRM standards
Build Sales Enablement Materials
- Create and organize sales playbooks, battle cards, and objection handling guides based on direction from leadership
- Develop onboarding checklists and training materials for new sales hires
- Keep sales collateral organized and accessible—maintain a content library that reps can actually use
- Coordinate with Product and Marketing to gather and distribute product updates and competitive intel
Support GTM Planning & Operations
- Work with the fractional GTM executive to implement processes and operational changes
- Help administer territory assignments and compensation plan tracking
- Prepare data and analysis to support leadership decision-making
- Document processes and create SOPs as new workflows are established
Manage Day-to-Day Sales Tools
- Be the go-to person for HubSpot questions and troubleshooting
- Set up and maintain integrations between HubSpot & any other sales tools
- Research and recommend new tools as needs arise
Who You Are
- 3-5+ years of experience in sales operations, revenue operations, or sales enablement
- Solid HubSpot skills—comfortable building workflows, reports, and dashboards
- Strong attention to detail and organizational skills
- Proficient in Excel/Google Sheets—can build models, pivot tables, and VLOOKUPs
- Clear communicator who can document processes and create training materials
- Self-motivated and able to manage multiple projects with minimal oversight
- Comfortable taking direction and executing against a defined plan
Nice to Have
- Experience in HR tech, benefits, insurance, or B2B SaaS
- Familiarity with broker or channel partner sales models
- Exposure to sales methodologies like MEDDIC or Challenger
- Experience with other GTM tools like ZoomInfo or Outreach
Compensation & Perks
- Competitive base salary
- 100% company-paid health insurance
- Opportunity to learn GTM strategy from experienced leadership
- High-visibility role with direct exposure to company growth
- Collaborative, mission-driven team
Travel Requirement: Minimal (less than 10%)—primarily remote with occasional travel for team meetings.