Senior Manager, Revenue Automation & AI

About OpenLoop

OpenLoop was co-founded by CEO, Dr. Jon Lensing, and COO, Christian Williams, with the vision to bring care anywhere. Our telehealth support solutions are thoughtfully designed to streamline and simplify go-to-market care delivery for companies offering meaningful virtual support to patients across an expansive array of specialties, in all 50 states.

About the Role

Most revenue teams talk about AI. Fewer have it running in production. At OpenLoop, AI agents are already enriching leads, recategorizing support tickets, parsing contracts, and moving data between HubSpot, Jira, Stripe, and Slack. We're looking for a Senior Manager of Revenue Automation & AI to own where that goes next.

This is a player-coach role. You'll own the AI and automation roadmap for the entire go-to-market organization—Sales, Marketing, Customer Success, and Revenue Operations—and you'll lead the analyst pod that builds it. You'll also still be in the tools yourself every week. We're not hiring someone to advise on AI. We're hiring someone to ship it, measure it, and keep it running.

You'll partner with Revenue Systems, Revenue Intelligence, Finance, and GTM leadership, and you'll grow a team of automation analysts as the function scales. If you'd rather build the thing than write the deck about the thing—and manual work that a well-designed workflow should be handling genuinely bothers you—this role was written for you.

What You'll Do

• The Automation Roadmap – Own a single intake and prioritization path for GTM automation requests—scored on impact and effort, reconciled against team capacity, and visible to stakeholders. You decide what gets built, what waits, and what gets declined.

• AI Agents in Production – Design, build, and maintain the agents that power the revenue motion—prospecting and AI SDR workflows, enrichment pipelines, MQL classification and intent filtering, and competitive intelligence—so the outbound and inbound engines run with less human handling.

• Revenue Workflow Automation – Own the automation layer across HubSpot, Jira, Slack, and Salesforce—workflows triggered by deal stage, client status, and operational events—so handoffs happen the same way every time without someone remembering to run them.

• AI Output Quality – Set and enforce the quality bar for AI output—evaluating what the model is actually solving for, not just whether it ran—backed by documented runbooks, monitoring, and alerting on failure. An automation nobody is watching is a liability, not an asset.

• Impact Measurement – Build and defend the measurement model for hours returned, cost avoided, and revenue influenced. Methodology is agreed with Finance and reported to the board, so it has to survive scrutiny.

• Team Leadership – Hire, ramp, coach, and develop a pod of automation analysts. You'll inherit strong builders and grow the seat count as the roadmap does.

• Adoption & Enablement – Partner with Revenue Enablement so what you ship actually gets used. Adoption is part of the build, not a follow-up project.

• Migration Durability – Partner with Revenue Systems through an active HubSpot to Salesforce migration to make sure the automation and AI layer lands on the other side intact.

Who You Are

• 5+ years in revenue operations, marketing operations, systems, or automation, including hands-on build ownership

• Experience leading a delivery pod—formal management, tech lead, or player-coach

• Expert-level HubSpot: workflows, custom objects, properties, and APIs

• Deep hands-on experience with at least one automation platform (Make.com, Zapier, Workato, or similar)

• You've built AI agents, not just used ChatGPT—prompt design, tool use, evaluation, and failure handling

• The judgment to critically evaluate AI output: knowing when to trust the model, when to dig, and when an answer looks right and isn't

• Comfort working across messy, multi-system data environments (CRM + financial systems + support + product data)

• Ability to build a business case and defend an impact number to Finance and executive stakeholders

• Experience through a CRM migration or platform consolidation a strong plus

• Familiarity with Clay, Claude Code, Salesforce, Zoho Desk, NetSuite, or Stripe data structures a plus

• Healthcare or other regulated-data experience, including PHI handling, a plus

Our Benefits

In addition, for salaried positions you would also be eligible for:

• Medical, Dental, and Vision plans

• Flexible Spending/Health Savings Accounts

• Flexible PTO

• 401(k) + Company Match

• Life Insurance, Pet insurance, and more

Our Company

We have a relatively flat organizational structure here at OpenLoop. Everyone is encouraged to bring ideas to the table and make things happen. This fits in well with our core values of Autonomy, Competence and Belonging, as we want everyone to feel empowered and supported to do their best work.

Sound like a good fit? We’d love to meet you.