Head of Insurance Operations · Fully Remote

This is a rare chance to build and own the entire revenue operations function at a growing AI-powered SaaS company – with direct access to senior leadership, a wide operational mandate, and the freedom to use cutting-edge AI tools to work smarter every day. Marketing Operations

• Own the end-to-end marketing technology stack, including marketing automation (HubSpot), data enrichment, analytics platforms, and other third-party software.
• Ensure clean data, compliance, and automation best practices across CRM and marketing systems.
• Use AI tools to automate insight generation from campaign data and surface actionable performance trends.
• Sales Operations & CRM Administration
• Serve as SundaySky’s primary Salesforce CRM administrator: own architecture, workflows, data integrity, user management, and reporting.
• Support pipeline management, sales forecasting, territory design, and quota-setting in close collaboration with Sales leadership.
• Maintain accurate ARR and CARR data in coordination with Finance, including new logos, expansion, churn, and downsell tracking.
• Deploy AI-assisted tools for data enrichment, duplicate detection, and ongoing data quality management.
• Administer and optimize sales engagement and intelligence tools (SalesLoft, Clari, ZoomInfo, and others) in coordination with Sales leadership.
• Monitor and report on KPIs across the full revenue funnel – from lead generation through customer expansion.
• Proactively surface actionable insights rather than just delivering data.
• Tech Stack & AI Implementation
• Own and administer the full RevOps tech stack; evaluate and implement new tools to enhance team performance and efficiency.
• Lead implementation of new AI workflows to accelerate operational work, automate reporting, and generate insights.
• 5–8 years of experience in Revenue Operations, Marketing Operations, or Sales Operations in a B2B SaaS environment, with ownership of both marketing and sales systems.
• Proven experience building marketing and sales operations infrastructure during periods of high growth.
• Certified Salesforce Administrator or equivalent hands-on admin experience required; you’re comfortable building and maintaining complex workflows, reports, and data structures.
• Deep expertise in marketing automation systems and processes (experience with HubSpot a plus).
• Ability to build and deliver executive-level dashboards and KPI reports.
• Comfortable owning the full RevOps tech stack and making smart decisions about what tools to keep, retire, or add.
• you translate data into decisions and can explain complex systems to non-technical audiences.
• Highly organized, data-obsessed, and self-directed; Bachelor’s degree in relevant field.

At SundaySky, we use AI tools like Claude as a primary accelerant for operational work, research, reporting, and content production.

~We treat AI fluency as a genuine career skill and invest in helping our team build it.

Remote – U.SundaySky is a pioneer in AI-powered video personalization, transforming how enterprise brands – particularly in banking, financial services, and insurance -- connect with their customers. Our platform delivers personalized, data-driven video experiences at scale, making every customer interaction uniquely relevant and engaging.

SundaySky is backed by Clearhaven Partners, a Boston-based private equity firm focused exclusively on software and technology businesses. This partnership provides us with operational resources and strategic expertise to accelerate our growth and market leadership.

We’re bringing on new team members who are drawn to fast-paced, rapidly growing software companies to join us in our mission to transform how businesses connect with audiences through personalized video.

At SundaySky, we prioritize the success of our customers and employees, emphasizing empathy, collaboration, excellence, and the happiness of our teams.