Director of Enterprise Sales

About the role

Rilla is a foundational company building the leading conversation intelligence software for offline commerce, enabling salespeople to record face-to-face conversations and leverage AI to improve their performance. The Director of Enterprise Sales will own the end-to-end strategy and execution of enterprise sales motions, driving both team performance and operational excellence. This hire is responsible for scaling the enterprise sales organization from the ground up while maintaining a relentless focus on customer outcomes and value realization. They will translate complex buyer landscapes into clear, repeatable sales playbooks that the entire organization can execute against with confidence. The role demands a leader who thrives on building systems that compound advantages over time in a high-velocity environment. Ultimately, this person will shape the future of how enterprise sales is done at Rilla, ensuring that the company's ambition matches its execution.

Key facts

What you'll do

Lead, grow, and develop a team of enterprise AEs, setting a high bar for pipeline, deal quality, and quota attainment while coaching the team hard to clear these standards consistently.

Design and own how enterprise sales operates at Rilla, including the sales process, playbooks, and deal motions that convert complex, multi-stakeholder engagements into predictable and scalable wins.

Coach your reps to become trusted advisors for enterprise buyers, guiding them through long sales cycles, multiple stakeholder alignments, procurement processes, and security evaluations while selling outcomes instead of mere features.

Remain deeply involved in the largest and most strategic deals, working side-by-side with your reps to demonstrate excellence and close the toughest opportunities in the portfolio.

Own the accuracy and reliability of the sales forecast, defining the key metrics that matter such as pipeline coverage, win rate, cycle time, ACV, and net new ARR, and instituting rigorous pipeline reviews and accountability mechanisms.

Serve as the primary voice of the customer within the enterprise funnel, capturing prospect pain points and requirements to shape the Rilla product roadmap with sharp, data-driven, and prioritized feedback.

Partner cross-functionally with Marketing, SDRs, Customer Success, and Product to deliver a seamless buyer experience from initial contact through closure and expansion, actively removing internal friction that stalls deal momentum.

Establish and refine the metrics, tools, and rituals that allow enterprise sales to operate at scale without sacrificing quality, predictability, or customer trust.

Champion a culture of ownership, learning, and rigor, ensuring that every rep understands the business impact of their activities and the rationale behind every process decision.

Drive continuous improvement by analyzing performance data, competitive moves, and market signals to iterate on strategy, messaging, and execution in real time.

Requirements

You are a customer-obsessed leader who measures success by the outcomes your customers achieve rather than by vanity metrics or superficial activity.

You are an infinite learner who constantly seeks new knowledge, moves quickly through ambiguity, and grows uncomfortable with any sense of complacency in your work.

You are a team-first leader who believes in giving and receiving candid feedback, and who measures personal growth by the collective advancement of the group.

You embrace failure as a necessary step toward mastery, taking intelligent risks and extracting lessons that make you and your team better over successive attempts.

You practice extreme focus in all decisions, rigorously prioritizing time, resources, and attention to maximize efficiency and impact.

You operate under the principle that the best teams function like a high-speed reinforcement learner, iterating millions of times to achieve near-perfect execution.

You are a proven top enterprise closer who has repeatedly beaten ambitious quotas by mastering complex, multi-stakeholder deals that other sellers could not close.

You are ready to step into full leadership and build a repeatable sales machine, while actively developing your people and passing on the playbook that made you successful.

You have the experience and skillset to coach enterprise reps through long cycles, multiple committees, procurement, and security reviews while guiding them to build executive-level trust.

You value clarity in communication and decision-making, ensuring that expectations, metrics, and feedback are transparent and actionable for everyone involved.

Nice to have

You were an early employee at a fast-scaling startup where you had to build processes from limited resources.

You have a track record of selling behavior-change, coaching, or enablement products where the win is getting an entire team to operate differently, not merely securing a contract signature.

You have hands-on experience mentoring or coaching sales reps on the side and are now prepared to do this at scale within a formal leadership role.

Practical notes

The position is full-time and based in New York City.

Candidates must be able to commit to an in-office schedule consistent with the company's operating rhythm.

No specific hours, visa sponsorship, travel requirements, or application deadlines are defined in the source material.