Vice President of Sales, North America

LivePerson

1d•Remote

About The Position

LivePerson (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 LivePerson the #1 Most Innovative AI Company in the world. As the VP of Sales, North America, you will be the primary architect of growth and the strategic leader for all sales operations across the North American region (US, Canada, and Mexico). Your mission is to scale our market presence by leading a diverse, high-performing team focused on high-velocity growth within the Fortune 500. The single most important outcome you will be responsible for is driving sustainable, predictable revenue growth while establishing LivePerson as the gold standard for conversational commerce across North America and Canada. This role requires a data-driven leader who leads, maintains, and develops a team of high performing quota carrying professionals who successfully accelerate “ramp-to-quota” while serving as the executive senior sales leader sponsor on marquee digital transformation deals. The role requires a data driven leader who can navigate complex client situations including procurement hurdles while fostering a relentless “hunter” mindset across a collaborative, customer-obsessed organization. Reporting to the Field Office President - Chief Revenue & Customer Officer, this role sits at the heart of our international expansion strategy. You Will: Key Responsibilities & Impact Attributes & Mindset: Entrepreneurial Leadership: A proactive, results-oriented leader who thrives in ambiguous environments and can pivot strategies based on competitive market shifts. Exceptional Communicator: Capable of translating "the future of AI" into clear business outcomes for executive stakeholders. Inclusive People Leader: A passion for building diverse teams and a "success is shared" mentality, where your primary motivation is the growth of your individual contributors.

Requirements

15+ years of professional experience in SaaS/Cloud sales, with at least 7-10 years in a senior leadership capacity overseeing the United States and Canada region.
Bachelor’s degree in Business, Marketing, or a related field; an MBA or equivalent practical executive experience is highly regarded.
Proven Track Record: A documented history of overachieving quotas and scaling regional revenues from mid-eight to nine figures in a high-growth environment.
Conversational AI Fluency: Deep knowledge of the SaaS landscape, with the ability to articulate complex AI-driven value propositions and ROI to technical and non-technical audiences.
Sales Methodology: Expert-level proficiency in modern sales methodologies (e.g., MEDDPICC, Challenger, Value Selling) and a commitment to data-driven pipeline management via Salesforce.
GTM Strategy: Demonstrable experience in building both direct sales engines and indirect partner/channel ecosystems simultaneously.
Demonstrated experience in sales coaching and professional development, with a proven ability to accelerate the "ramp-to-quota" across a team with skills at varying levels with proven success in elevating the output of mid-level performers into top-tier territory achievers.
Experience in influencing and 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 through underperformance and build incentive structures that celebrate and retain over-achieving talent.
Growth Mindset: You are curious, embrace coaching, and view feedback or failure as a mandatory fuel for growth.
Entrepreneurial Spirit: You are a self-starter who thrives in fast-paced, dynamic environments and can inspire passion in others.
Customer-Obsessed: You deliver excellence in service and are committed to fostering a collaborative team environment to achieve the best results for the client.

Responsibilities

Scale and lead 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 lead the team’s key performance indicators that drive success, proactively addressing underperformance while celebrating and rewarding over-achievement.
Serve as the executive on marquee deals, leveraging your presence to build trust with C-suite stakeholders at Fortune 500 prospects.
Serve as key decision maker to the sales team on critical sales deals.
Coach, mentor, and drive the sales 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 support AEs in navigating the complex stakeholder maps and procurement hurdles typical of multi-million dollar enterprise contracts.
Oversee and direct the team 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 and executive leadership to ensure the AI roadmap stays ahead of market demand.
Collaborate with Marketing to optimize lead quality and ensure account-based marketing (ABM) efforts are tightly aligned with your team’s top-target accounts.

Benefits

Medical, Dental, and Vision Insurance: Comprehensive plans to support your health needs.
Wellness Resources: Access to wellbeing resources and programs including our EAP plan.Health & Mental Support: Access a confidential and free Employee Assistance Program (EAP), providing professional counseling.
401(k) Retirement Plan: To help you plan for your financial future by offering both the plan and a 4% employer match (100% match on the first 3% contribution and 50% match on the next 2% contribution)
HSA & FSA Plans: To help you plan for health related expenses on a pre-tax basis
Employee Stock Purchase Program (ESPP): Participate and receive a discount on company shares, allowing you to directly share in LivePerson's success and growth.
Additional Insurances: Basic and supplemental life insurance, Accidental Death & Dismemberment (AD&D) insurance, long-term and short-term disability insurance coverage, legal plan, identity theft protection plan, and critical illness supplemental insurance.
Development: Access to internal professional development resources.
Flexible Paid Time Off (PTO): Discretionary PTO package for flexible days off with manager approval.
Paid Public Holidays.
Generous Parental Leave Policy: Including maternity/paternity support and fertility services.
Remote-First Model: This role is fully remote (#LI-Remote), offering excellent work-life balance and flexibility. We also maintain dedicated WeWork space for those who wish to meet colleagues or collaborate in person.