Founder-Led Sales: He Learned to Sell and Closed 50 Customers

Summary

This The SaaS Podcast episode features Omer Khan interviewing Shahar Azulay about building Groundcover into an observability company that he says has approximately $20 million in ARR, 250 customers, and 150 employees. The case joins eBPF Observability and Observability Cost Architecture to Founder-Led Sales: a kernel-level sensor and bring-your-own-cloud data plane support infrastructure-based pricing, while direct founder ownership of prospecting, demos, proofs of concept, negotiation, and customer feedback helped the company learn how to sell. It also adds an Incumbent Replacement Migration boundary: displacing Datadog or New Relic required product maturity, positioning, migration support, and verification that customers actually retired the incumbent.

Key Claims

• Groundcover provides full-stack observability for cloud applications and infrastructure, with product and R&D in Tel Aviv and its main go-to-market organization in the United States.
• Shahar Azulay reports that Groundcover had approximately $20 million in ARR, 250 customers, and 150 employees at the time of the interview.
• The product combines an eBPF-based sensor with a managed backend whose data plane runs in the customer’s environment.
• Groundcover charges mainly according to monitored infrastructure, such as host count, instead of log, metric, and trace volume; the architecture is meant to reduce incentives to sample or disable telemetry because of ingestion cost.
• The founders began experimenting with eBPF near the end of 2021 and deployed a self-hosted early system to their first customer roughly three months later.
• The first product lacked its own user interface and used Grafana dashboards; the first buyer initially treated it as a complementary tool for specialized visibility rather than a Datadog replacement.
• Shahar proposed $100,000 to the first customer, accepted a three-year agreement at $10,000 per year, and treats the underpriced deal as paid organizational learning about procurement, security, legal review, value, and negotiation.
• Groundcover needed roughly 50 customers to reach its first $1 million in ARR; Shahar personally handled prospecting, discovery, demos, proofs of concept, pricing, and closing.
• He estimates that early prospecting consumed 30%-40% of his time and often involved 10-15 personalized contacts per productive day through LinkedIn, email, personal networks, events, and product engagement.
• The company struggled to convert the founder’s intuitive motion into repeatable recruiting, training, evaluation, and management for account executives, sales engineers, and SDRs.
• Groundcover’s first 20-30 customers generally used it in greenfield or complementary roles; by late 2024 or early 2025, product maturity and positioning supported more full-replacement evaluations.
• Replacement selling required a migration and post-sales process: a signed contract was not enough when customers continued using Datadog for unresolved use cases.
• By 2025 the company sold closer to list price, and by early 2026 it had pricing approaches that let customers begin migration before incumbent contract renewal.

Key Quotes

“X-ray of software” - Shahar’s analogy for the visibility eBPF can provide into applications and infrastructure.

“almost any price” - the episode’s framing of Shahar’s advice to prioritize learning and customer closure in the first dozen opportunities.

Connections

• Shahar Azulay - Groundcover co-founder and CEO describing the product, first customers, and sales-learning process.
• Groundcover - observability company at the center of the episode.
• The SaaS Podcast and Omer Khan - show and interviewer context.
• eBPF Observability - kernel-level telemetry approach behind Groundcover’s sensor.
• Observability Cost Architecture - connection among data-plane location, telemetry volume, pricing unit, and customer coverage decisions.
• Observability - broader operating discipline that Groundcover sells into.
• Founder-Led Sales and Sales As Learnable Skill - direct customer work and repeated practice through which Shahar learned selling.
• Enterprise POC Discipline - adjacent proof-of-concept discipline for technical enterprise evaluations.
• Incumbent Replacement Migration - requirement to make migration, expectation alignment, and incumbent retirement part of the sale.
• Stage-Appropriate Hiring - constraint exposed when Groundcover tried to build a repeatable sales organization.

Contradictions

• No settled contradiction with existing wiki content. The source strengthens Founder-Led Sales as a learning loop while showing that early willingness to accept weak pricing should change as product maturity, references, replacement scope, and leverage grow.
• The episode qualifies a simple “better technology wins” account: eBPF and bring-your-own-cloud created differentiation, but full incumbent displacement still depended on feature coverage, messaging, migration execution, and post-sales verification.
• ARR, customer, employee, contract, timing, pricing, outreach, and migration figures are retained as source-scoped statements from Shahar and the episode framing.