LPSN Stock: Insider Activity, Filings & Research
LivePerson, Inc. (LPSN) — Drillr’s hub for LPSN insider activity, SEC filings, earnings signals and AI research. Over the trailing 3 months, LPSN insiders filed 0 open-market buys and 7 sales (SEC Form 4). 1 published research article, SEC filings and AI analysis on Drillr.
LPSN insider trading activity (SEC Form 4)
| Date | Insider | Type | Shares | Price |
|---|---|---|---|---|
| May 19, 2026 | Greenberg Monica L.officer: EVP, Policy & General Counsel | Sell | 3,600 | $2.18 |
| May 19, 2026 | Collins John DeNeenofficer: CFO and COO | Sell | 7,203 | $2.18 |
| Apr 2, 2026 | Sabino Anthony Johndirector, officer: Chief Executive Officer | Sell | 7,844 | $2.57 |
| Mar 25, 2026 | Sabino Anthony Johndirector, officer: Chief Executive Officer | Sell | 8,033 | $2.50 |
| Mar 17, 2026 | Sabino Anthony Johndirector, officer: Chief Executive Officer | Sell | 12,594 | $2.72 |
| Mar 17, 2026 | Collins John DeNeenofficer: CFO and COO | Sell | 931 | $2.72 |
| Mar 17, 2026 | Greenberg Monica L.officer: EVP, Policy & General Counsel | Sell | 315 | $2.72 |
| Mar 16, 2026 | Collins John DeNeenofficer: CFO and COO | Grant | 1,851 | — |
| Mar 16, 2026 | Greenberg Monica L.officer: EVP, Policy & General Counsel | Grant | 833 | — |
| Jan 20, 2026 | Mina Christopher Allenofficer: Chief Tech Product Officer | Sell | 7,152 | $3.15 |
| Jan 7, 2026 | Collins John DeNeenofficer: CFO and COO | Grant | 34,193 | — |
| Dec 18, 2025 | Miller James R.director | Sell | 2,133 | $4.73 |
| Dec 17, 2025 | Sabino Anthony Johndirector, officer: Chief Executive Officer | Sell | 4,984 | $4.73 |
| Dec 12, 2025 | Lane Nathandirector | Grant | 23,350 | — |
| Dec 12, 2025 | Vardeman Ryan L.director | Grant | 23,350 | — |
Source: LPSN SEC Form 4 filings, latest May 19, 2026. For informational purposes only — not investment advice.
LivePerson, Inc. company profile
Overview
LivePerson, Inc. (NASDAQ:LPSN) is a conversational commerce and artificial intelligence software company founded in 1995 and headquartered in New York. The company went public in 2000 and has evolved from providing basic online chat services to becoming a comprehensive conversational AI platform provider. LivePerson operates through its cloud-based Conversational Cloud platform, enabling businesses to engage with customers through messaging, voice, and AI-powered interactions. The company has undergone significant strategic transformation in recent years, focusing on AI-driven solutions while streamlining operations and improving its capital structure through partnerships and cost reduction initiatives.
Business
LivePerson operates in the conversational commerce and customer engagement software industry, providing cloud-based platforms that enable businesses to communicate with their customers through digital messaging channels. The company's core offering is the Conversational Cloud, an enterprise-grade platform that integrates various communication channels including mobile messaging, web chat, voice, and social media into a unified customer engagement solution. The Conversational Cloud serves as a comprehensive customer service and sales platform that allows businesses to manage customer interactions across multiple touchpoints. The platform incorporates artificial intelligence capabilities to automate conversations, route inquiries to appropriate agents, and provide real-time assistance to both customers and human agents. Key features include AI-powered chatbots, conversation orchestration, analytics, and integrations with popular business systems and voice platforms like Avaya, Amazon Connect, and Cisco. LivePerson operates through two main business segments: The Business segment (representing the vast majority of revenue at approximately 85-90%) focuses on enterprise customers and provides the core Conversational Cloud platform along with professional services for implementation and optimization. The Consumer segment (representing roughly 10-15% of revenue) facilitates direct transactions between experts and consumers seeking information through messaging platforms. The company also generates revenue through professional services, which include consulting, implementation, and training services that help customers maximize the value of their conversational AI investments.
Revenue model
LivePerson generates revenue through multiple streams within its software-as-a-service business model. The primary revenue source is recurring subscription revenue from its Conversational Cloud platform, which accounts for approximately 93-94% of total revenue. Customers pay based on usage metrics such as the number of conversations handled, active users, or messaging volume, creating a scalable pricing model that grows with customer engagement. The company's paying customers are primarily enterprise businesses, including Fortune 500 companies, online merchants, automotive dealers, healthcare organizations, financial services firms, and government agencies. These organizations use LivePerson's platform to handle customer service, sales inquiries, and support across digital channels. The average revenue per customer is approximately $625,000-$640,000 annually, indicating a focus on large enterprise accounts. Professional services represent the secondary revenue stream, generating around 15-20% of total revenue through implementation, consulting, and training services. The company also offers partner-enabled sales, targeting a 35% partner attachment rate where third-party system integrators and consultants help sell and implement LivePerson solutions. Several factors influence LivePerson's margins and profitability. Positive margin drivers include the scalable nature of cloud software, increasing adoption of AI features that command premium pricing, and operational efficiency improvements from recent cost reduction initiatives. Negative margin pressures come from intense competition in the customer experience software market, customer churn during economic uncertainty, cloud infrastructure migration costs, and the need for continued investment in AI and product development to maintain competitive positioning. The company's margins are also affected by the mix between higher-margin recurring software revenue and lower-margin professional services.
Competitive moat
LivePerson's competitive moat is moderate but faces significant challenges. The company's primary defensive advantages include its extensive conversational data set accumulated from processing over 1 billion conversations annually, which provides valuable training data for AI model development. This data advantage, combined with nearly three decades of experience in conversational interfaces, creates some barriers to entry for newer competitors. The platform's integration capabilities and established enterprise relationships provide additional moat strength. LivePerson has built deep integrations with major contact center platforms like Avaya, Amazon Connect, and Cisco, making it costly and complex for customers to switch providers. The company's focus on regulated industries such as healthcare, financial services, and telecommunications also creates switching costs due to compliance and customization requirements. However, LivePerson's moat faces substantial competitive pressure. The conversational AI and customer experience software market is highly competitive, with well-funded competitors including Salesforce Service Cloud, Microsoft's customer service solutions, and specialized players like Zendesk and Intercom. Many of these competitors have significantly larger resources and broader product portfolios. Additionally, the rapid evolution of AI technology means that LivePerson's current technical advantages could be quickly eroded by competitors with superior AI capabilities or more comprehensive platform offerings. The company's recent financial struggles, customer churn, and declining revenue suggest that its moat may be weakening. With net revenue retention at 80-82% (well below the industry benchmark of 100%+), LivePerson is losing ground with existing customers, indicating that competitors may be offering more compelling value propositions. The company's small size relative to major competitors also limits its ability to invest in R&D and sales at the scale necessary to maintain competitive advantages in a rapidly evolving market.
Risks & safety
LivePerson presents moderate to high financial risk with limited margin of safety for investors. • Liquidity and Solvency: The company maintains $176 million in cash and short-term investments with a current ratio of 1.65, providing adequate short-term liquidity. However, free cash flow is negative at -$7.2 million in Q1 2025, indicating ongoing cash burn despite recent cost reduction efforts. • Debt and Capital Structure: The balance sheet shows total liabilities of $671 million against total assets of $596 million, resulting in negative book value of approximately -$75 million. The debt-to-equity ratio of -7.06 reflects the company's overleveraged position following the Lynrock Lake transaction. • Valuation Metrics: With negative earnings and EBITDA, traditional valuation metrics are not meaningful. The company trades at approximately 1.2x forward revenue based on 2025 guidance of $240-255 million, which appears reasonable for a declining SaaS business. • Operating Performance: Revenue has declined from $515 million in 2022 to an expected $240-255 million in 2025, representing a compound annual decline of over 20%. Net revenue retention of 80% indicates ongoing customer losses and downgrades. • Other Considerations: The company is targeting EBITDA breakeven to slightly positive in 2025, but this depends on successful execution of turnaround initiatives. The small market capitalization of $74 million creates high volatility risk and limited institutional interest.
Recent development
LivePerson has undergone significant strategic transformation over the past few years, driven by new leadership and market pressures. In 2024, the company executed a transformative capital structure agreement with Lynrock Lake, which improved its balance sheet but resulted in significant dilution to existing shareholders. This transaction was accompanied by aggressive cost reduction initiatives that removed over $30 million in annual expenses. The company has made substantial investments in artificial intelligence capabilities, with AI features now representing a key differentiator. Recent product launches include "Bring Your Own LLM" functionality, Copilot Rewrite, AI-powered conversation routing, and data collection AI agents. Over 70 customers are now paying for generative AI features, with AI-powered conversations growing 165% quarter-over-quarter. The company has also expanded its AI capabilities to include voice integration, launching Agent Workspace for Voice to provide omnichannel customer service capabilities. LivePerson has implemented a simplified pricing and packaging strategy to improve sales effectiveness and customer acquisition. The new bronze, silver, and gold packaging approach reduces complexity for customers and sales teams while creating clearer upgrade paths. The company has also installed new go-to-market leadership, including a new Chief Revenue Officer, and is targeting a 35% partner attachment rate to leverage third-party sales channels. Strategic partnerships have become increasingly important, with deepening relationships with Avaya, Amazon Connect, and Cisco to integrate LivePerson's conversational AI capabilities with popular contact center platforms. These partnerships are designed to make LivePerson's solutions more accessible to customers who want to enhance their existing technology investments rather than replace them entirely. The company expects these integrations to drive customer acquisition and reduce sales cycle complexity.
LPSN company profile · for informational purposes only — not investment advice.
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