Founding Enterprise Account Executive

OllyGarden, Inc.; Northern (KY); Hybrid; USD 150,000 - 220,000; Full time

Job summary

OllyGarden, Inc. is seeking a founding enterprise sales leader in the United States to drive the entire sales cycle from prospecting to close.

You will directly access the CEO and shape the motion before scaling it, owning discovery, technical evaluations, negotiations, and procurement. You will refine ICPs, messaging, qualification criteria, and the forecast with the founders, build repeatable playbooks, and hand off wins to Customer Success while engineering owns implementation.

Qualifications

• Proven record sourcing and closing complex B2B infrastructure or developer-tools deals.
• Credibility with observability, SRE, platform and engineering buyers.
• Experience building pipeline without reliance on mature SDR/RevOps.
• US-based with access to buyers and observability/infra communities.
• OpenTelemetry familiarity and connections to observability or infra buyers.
• Experience working directly with a technical founder.

Responsibilities

• Own prospecting, discovery, technical evaluations, proof-of-value, negotiation, procurement, and closing.
• Refine ICP, messaging, qualification criteria, forecasting, and objection handling with the founders.
• Build lightweight systems and operating rhythm that future sellers can reuse.
• Hand closed customers to Customer Success while engineering owns deep technical implementation.
• Lead technical discovery and evaluations connecting telemetry quality to measurable customer outcomes.
• Close initial enterprise customers and document a repeatable, evidence-based sales playbook.

Skills

Sourcing and closing complex deals

Credibility with observability buyers

Pipeline-building without mature SDR/

US-based with access to observability/

OpenTelemetry familiarity and network

Job description

This is a founding role with direct access to the CEO and broad ownership across the entire enterprise sales cycle. You will prove the motion yourself before helping us scale it.

What you’ll own

• Own prospecting, discovery, technical evaluations, proof-of-value conversion, negotiation, procurement, and closing
• Refine our ICP, messaging, qualification criteria, forecasting, and objection handling with the founders
• Build the lightweight systems and operating rhythm that future sellers can reuse
• Hand closed customers cleanly to Customer Success while engineering owns deep technical implementation

Outcomes that matter

• Build qualified pipeline with US observability, platform, SRE, and engineering leaders
• Lead technical discovery and evaluations that connect telemetry quality to measurable customer outcomes
• Close initial enterprise customers and document a repeatable, evidence-based sales playbook
• Establish trustworthy qualification, forecasting, procurement, and founder collaboration rhythms

What we’re looking for

• A quantified record of personally sourcing and closing complex B2B infrastructure or developer-tool deals
• Credibility with observability, SRE, platform, and engineering buyers
• Experience building pipeline without depending on a mature SDR, marketing, or RevOps organization
• US-based, with practical access to buyers and relevant observability and infrastructure communities
• OpenTelemetry familiarity and an existing network among observability or infrastructure buyers
• Experience working directly with a technical founder

Show us how you sell

The process is practical and evidence-led. We want to understand how you create demand, earn technical trust, move complex deals, and learn with a small founding team.

• 01

  A conversation about the markets you know, the deals you personally sourced and closed, and why OllyGarden interests you

• 02

  A practical working session using a real account to show how you research, qualify, and open a technical enterprise opportunity

• 03

  A discovery and deal-strategy exercise with the founders, including how you handle technical proof, objections, and procurement

• 04

  Reference conversations focused on ownership, forecast accuracy, collaboration, and customer trust