Director of Enterprise GTM

Reports to CEO

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.

• 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

• 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.
  

• 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.

• 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

• 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.

• 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 with strong conversion into pilots and long-term contracts.

• Increased leverage for the CEO to focus on fundraising, brand, and strategic partnerships without loss of GTM momentum.

• Proven experience in enterprise GTM, business development, or partnerships.

• Deep, trusted relationships in higher education or other high-volume, call-center-driven industries (travel, insurance, etc.)

• Highly accountable and motivated by owning outcomes, not just activity

• Strong understanding of how call centers operate, including lead conversion, engagement, enrichment, and retention workflows, with an appreciation for how one-time conversions evolve into long-term customer relationships and lifecycle value

• Existing relationships with call center leaders, operators, or vendors, and an understanding of how these organizations evaluate revenue-impacting technology

• Comfortable operating in ambiguity and building systems from relationships

• Strong executive presence and credibility in senior-level conversations

• Comfortable working in AI-native, product-driven organizations and using modern operational tools such as Linear and Notion to surface insights for product and engineering teams

• Bonus but not required former founder or early founding team experience.

This is not a traditional sales role.

This is not sales development.

This is not partnerships as usual.

This role is about access, credibility, and leverage. It is a chance to help build a new GTM category that blends founder-led selling, relationship-driven growth, and AI-powered execution into a scalable enterprise engine.

• Competitive compensation in (salary + equity—we share the upside).

• Medical, dental, and vision insurance.

• 401(k) match.

• Life, Short-Term, and Long-Term Disability Insurance.

• Paid Parental Leave & Flexible Time Off.

• In-person culture—work alongside a rock-star team in Miami’s Arts & Entertainment District, five days a week.

OutRival builds tailored AI Digital Workers for large enterprises that drive revenue through proactive outreach, not just operational efficiency. We differentiate with a laser focus on the conversion metrics that matter most for our customers and with our AI deployments, we generate millions in incremental growth and retention revenue. Our founding team has spent over a decade building and running high-performing phone teams across the US, the Philippines, and Jamaica, reaching millions of prospects and guiding them through every stage of the buying journey. That experience shapes how we build Digital Workers with personalization and genuine empathy at every touchpoint, whether it is a student choosing a school, a consumer selecting insurance, or a family planning a trip.