Director of Enterprise Accounts

Outrival • Miami, FL

1d • Onsite

About The Position

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.

Requirements

• 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

Nice To Haves

• 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

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

Benefits

• 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.

What This Job Offers

• Job Type: Full-time
• Career Level: Director
• Education Level: No Education Listed
• Number of Employees: 11-50 employees