Director, Sales

Location: USA
Remote Status: Fully Remote

Live Person (NASDAQ: LPSN) is a leader in trusted enterprise conversational AI and digital transformation. The world's leading brands use our award‑winning Conversational Cloud platform to connect with millions of consumers. We power nearly a billion conversational interactions every month, providing uniquely rich data analytics and safety tools to unlock the power of conversational AI for better business outcomes. Fast Company named Live Person the #1 Most Innovative AI Company in the world.

We are seeking a seasoned Director of Sales to architect and execute Live Person’s North American enterprise strategy, focusing on high‑velocity growth within the Fortune 500. You will be responsible for the end‑to‑end performance of your team, from identifying top‑tier talent and accelerating “ramp‑to‑quota” to serving as the executive sponsor on marquee digital transformation deals. This role requires a data‑driven leader who can navigate complex procurement hurdles while fostering a relentless “hunter” mindset across a collaborative, customer‑obsessed organization.

• People Leadership & Talent Development
  • Scale the North American enterprise team by identifying high‑caliber Account Executives capable of navigating complex sales cycles
  • Elevate team performance through coaching and personalized growth tracks, focused on moving high‑potentials into top‑tier performers and maintaining a culture of “A‑player” excellence
  • Cultivate a transparent, high‑energy environment that balances a competitive “hunter” instinct with a collaborative “win‑as‑a‑team” philosophy
  • Define and manage the key performance indicators that drive success, proactively addressing underperformance while celebrating and rewarding over‑achievement

• Serve as the executive “closer” on marquee deals, leveraging your presence to build trust with C‑suite stakeholders at Fortune 500 prospects
• Coach your team to pivot from “feature‑selling” to “value‑selling,” helping them articulate the business impact of Conversational AI
• Architect high‑opportunity clusters across North America, ensuring AE portfolios are balanced for optimal “Land and Expand” potential
• Participate in strategic deal reviews to help AEs navigate the complex stakeholder maps and procurement hurdles typical of multi‑million dollar enterprise contracts

• Maintain a pulse on the health of the North American sales funnel, providing executive leadership with accurate monthly and quarterly ARR projections
• Refine the end‑to‑end sales lifecycle—from prospecting to closing—and ensure the team is effectively utilizing the sales tech stack (CRM, lead gen, etc.) to drive efficiency
• Conduct rigorous pipeline reviews to ensure consistency in lead flow and to identify early‑stage gaps

• Act as the “voice of the customer,” funneling insights from your AEs’ field experience back to Product teams to ensure the AI roadmap stays ahead of market demand
• Partner with Marketing to optimize lead quality and ensure account‑based marketing (ABM) efforts are tightly aligned with your team’s top‑target accounts

• Professional Experience & Education
  • 12+ years of SaaS sales experience; 8+ years in a formal people management role
  • Extensive experience in Strategic Value‑Based Selling, including buyer group identification and complex business case definition
  • Proven track record of success in SaaS, BPO, e‑commerce, or online marketing sales environments
  • Bachelor’s Degree of equivalent
• People Leadership Experience
  • Demonstrated experience in sales coaching and professional development, with a proven ability to accelerate the “ramp‑to‑quota” for new hires and elevate the output of mid‑level performers into top‑tier territory achievers
  • Experience fostering a high‑performance culture that successfully balances a relentless “hunter” mentality with a collaborative, team‑oriented approach to winning large‑scale enterprise deals
  • Proficiency in establishing and managing rigorous KPIs, with the ability to proactively coach…