Director of Enterprise Accounts

OutRival is building a relationship-led enterprise motion in which trust, executive alignment, and measurable outcomes drive decision-making. We're hiring our first Director of Enterprise Accounts to own enterprise revenue execution and help define how our enterprise sales function operates and scales.

This role is built for a high-ownership operator who can run consultative discovery, drive complex enterprise deal cycles end-to-end, and move opportunities through security, legal, procurement, and signature without needing heavy enablement or layers of process. In this role you will be working with executives such as CEOs, Presidents, CFOs, CMOs, VP of Sales, and VP of Enrollment, so executive presence is a must.

The founders and the GTM team handle pipeline sourcing. Your job is to convert qualified introductions and active opportunities into signed contracts and expansions with speed, rigor, and customer obsession.

Responsibilities:

• Full Ownership: Own enterprise new logo revenue execution from qualified introduction to signature

• High Agency & Creative: Design and execute pilots that demonstrate value quickly and convert quickly to enterprise contracts

• Listen and Educate: Lead consultative discovery and align stakeholders on measurable outcomes, success criteria, and ROI

• Orchestrate Decision buy-in: Run executive-level sales processes with multi-threaded buying committees across enrollment leaders, IT, finance, security, and legal

• Dial-up Momentum: Lead negotiations and contract processes in close partnership with legal and finance

• Make our AI Digital Workers & Platform Better: Orchestrate internal resources across founders, product, engineering, compliance, and delivery to win and expand accounts

• Challenge the status quo: Define and continuously improve the enterprise sales motion to refine stages, exit criteria, forecasting, and templates that improve win rate and velocity

• 10+ years of enterprise SaaS sales experience with a track record of closing large, complex deals

• Experience carrying a seven-figure quota or consistently closing $500K+ ACV enterprise agreements end-to-end

• Proven ability to navigate procurement, security reviews, legal redlines, and executive alignment without losing momentum

• Strong written and verbal communication with crisp follow-ups, proposals, and executive-level storytelling

• High judgment and rigor in forecasting, deal qualification, and pipeline management

• Owner mindset, comfort in ambiguity, and the ability to build lightweight systems while driving results

• Experience selling into higher education with a deep understanding of enrollment cycles, institutional governance, and university decision-making

• Early-stage founder or first enterprise sales hire experience where you built a process while carrying a quota

• Experience with AI platforms, workflow automation, or contact center solutions

• Background with pilot or proof-of-concept selling motions

• Founding Sales role with direct line to founders and company strategy

• Strong pipeline momentum with major partnerships already in motion

• Shape the function by helping to define how enterprise sales works at OutRival as we scale

• Transformative technology solving real enrollment and retention challenges for institutions

• Generous Comp package as we want to directly incentivize and remove a ceiling to your impact and earning potential

OutRival is an equal opportunity employer. We celebrate diversity and are committed to creating an inclusive environment for all employees.

• 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.