Director of Enterprise GTM

Reports to CEO THE OPPORTUNITY OutRival is building a fundamentally different enterprise go to market motion. At OutRival, we believe you move at the speed of your relationships. Everything about how we grow is built around that belief. We do zero cold outreach. No mass SDR teams. No spray and pray tactics. Every enterprise conversation starts with trust, context, and a warm introduction. Our growth is driven by deep relationships with senior operators, founders, and decision-makers inside high-volume organizations across higher education, insurance, and travel. These organizations care deeply about lead conversion, engagement, enrichment, and long-term customer retention. We are hiring a Director-level enterprise GTM leader who can personally generate qualified enterprise introductions through their own network, shape early conversations, and help build a repeatable, relationship-led growth engine alongside the CEO. This role is for a seasoned GTM or business development leader who is well-connected, credible in executive rooms, and excited to be accountable for turning relationships into results. WHAT YOU WILL OWN ENTERPRISE INTRODUCTION GENERATION - Personally generate a significant portion of qualified enterprise introductions through your existing network, with a strong focus on higher education and adjacent high-volume industries (travel, insurance, etc.) - Open doors to senior buyers and operators with real influence over budget and deployment - Take early ownership of discovery conversations to ensure strong ICP fit and clear paths to pilots and expansion - Commit to and own a clearly defined annual target for qualified enterprise opportunities - This role requires an existing, active network of senior leaders and the ability to immediately activate that network to generate qualified introductions RELATIONSHIP-LED PIPELINE GROWTH - Deliver 100–200+ qualified enterprise prospects annually through warm introductions and relationship-driven referral paths. - Ensure opportunities align with OutRival’s ICP and an ACV of $1M–$5M+ - Help shape how early conversations translate into pilots and long-term contracts. - Drive inbound enterprise interest through credibility, reputation, conferences, content, and trusted referrals. STRATEGIC DEAL SHAPING - Support CEO-led and founder-led enterprise conversations as a strategic partner. - Help multi-thread relationships inside complex organizations where multiple stakeholders influence decisions. - Identify where trust already exists inside an account and how to leverage it effectively. RELATIONSHIP INFRASTRUCTURE - Help formalize and improve how trusted external relationships are activated, coordinated, and supported. - Create lightweight playbooks, positioning guidance, and onboarding materials that ensure consistency and quality across introductions. - Participate in selective group sessions, working meetings, or events that strengthen relationship density across the ecosystem. - Ensure insights from discovery conversations are captured and shared internally - Exercise strong judgment around which opportunities to pursue, which conversations to accelerate, and which to politely decline in order to protect focus and signal CROSS FUNCTIONAL COLLABORATION - Work closely with the CEO, VP of Engineering, Chief Product Officer, and forward deployed digital worker managers. - Translate enterprise needs into successful digital worker deployments. - Support scaling digital workers into high-volume businesses focused on turning one-time conversions into long-term customer relationships. WHAT SUCCESS LOOKS LIKE - Ownership of a clearly defined annual pipeline number tied to qualified enterprise prospects - First qualified introductions generated within the first 7–30 days - Clear traction in the first 90 days, including multiple high-quality enterprise introductions and active discovery conversations sourced directly from your network. - A steady, predictable flow of enterprise opportunities