About the role
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. OpenLoop is building a modern, AI-enabled GTM tech stack—and we need the right person to own it. We’re looking for a Director of Revenue Systems & AI to lead the architecture, administration, and evolution of the full suite of tools that power our revenue organization: from Salesforce and HubSpot to call recording, conversation intelligence, and the broader GTM stack. This role is about more than implementing software. It’s about designing a systems environment where AI and automation aren’t afterthoughts—they’re built in from the start. You’ll help our revenue teams work smarter by giving them tools that reduce friction, surface the right information at the right time, and eliminate the manual work that pulls reps away from selling and customers away from success. This role is part builder, part strategist, and part pragmatist. You’ll set the technical vision for our GTM systems, lead implementation, and ensure that every tool we deploy actually gets used—and actually drives results. Why This Role Exists Our GTM tools have grown faster than our ability to manage them strategically. HubSpot powers our marketing engine, Salesforce is being built out for Sales and Customer Success, call recording and conversation intelligence tools are generating valuable data—but without unified ownership and a clear architecture, these systems create silos rather than leverage. Manual workarounds, inconsistent data, and disconnected tooling are creating drag across the revenue org—and leaving significant productivity gains on the table. This role brings unified ownership to the entire systems landscape. From CRM architecture to marketing automation to conversation intelligence, you’ll ensure every tool is configured for scale, integrated with the others, and set up to support AI-powered workflows from day one. What You’ll Own CRM Architecture & Implementation – Lead the design and buildout of Salesforce for Sales and Customer Success, ensuring the data model, objects, and workflows are built to support automation and AI from day one—not retrofitted later. Maintain Salesforce as the authoritative system of record for pipeline, revenue, and customer data AI Strategy & Execution – Identify, evaluate, and implement AI-powered tools and workflows that measurably improve revenue team productivity—from intelligent lead scoring and forecasting assistance to automated follow-up and deal insights Automation at Scale – Design and deploy automation that eliminates repetitive manual work across the GTM org, freeing reps and CS teams to focus on high-value, human-centric work Systems Strategy – Own the full GTM tech stack: Salesforce for Sales and CS, HubSpot for Marketing, call recording and conversation intelligence tools (e.g. Gong, Chorus), and any additional GTM tooling. Define how these systems integrate, where ownership sits, and what the future state architecture looks like as the business scales Integrations – Own system integrations and ensure seamless, reliable data flow across the full suite of GTM tools—because AI is only as good as the data it runs on Governance – Establish and enforce standards for system configuration, naming conventions, field management, and change control that keep the stack clean and scalable Data Quality – Drive CRM adoption and own the data quality initiatives that make reporting trustworthy, forecasting reliable, and AI outputs meaningful Tool Evaluation – Assess and implement new GTM tools—including emerging AI applications—balancing innovation with stack coherence and total cost of ownership Team Leadership – Build out and lead a Systems team spanning CRM administration, marketing automation, and GTM tooling—defining team structure, hiring, and developing talent as the systems portfolio grows What We’re Looking For 8+ years in Revenue Operations, Sales Operations, or GTM Systems roles Deep, hands-on expertise in Salesforce architecture and implementation—you can design the data model and also roll up your sleeves when needed Genuine enthusiasm for AI and automation in GTM contexts—you stay current on what’s emerging and have practical experience applying it to real business problems Hands-on experience with HubSpot—ideally as a marketing automation platform—and familiarity with call recording or conversation intelligence tools (Gong, Chorus, or similar) Experience leading CRM migrations or major system transformations Systems thinker with a strong bias toward scalable, clean architecture—you build for where the business is going, not just where it is Track record driving CRM adoption and data quality in fast-moving organizations Strong cross-functional collaborator—you build trust with both technical and non-technical stakeholders, and you can translate between them How We’ll Measure Success CRM Adoption – Active usage rates across GTM teams Data Quality – Completeness and accuracy scores across key fields System Reliability – Uptime and issue resolution time Implementation Velocity – Time to deploy system enhancements and new features Automation ROI – Reduction in manual workflows and hours saved across revenue teams AI Impact – Measurable productivity gains attributable to AI-powered tools and workflows Systems Roadmap Delivery – On-time delivery of systems roadmap milestones across Salesforce, HubSpot, and GTM tooling 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.
