Strategic Sales Representative

Position Overview

Cribl is seeking a Strategic Sales Representative who is a self-starter, naturally curious, and thrives in fast-paced, dynamic environments. A successful Strategic Rep at Cribl consistently generates their own pipeline, runs a disciplined sales process, and executes complex multi-product sales. You'll thrive here if you're someone who knows how to win on value—especially when you're not backed by a household name. You bring energy, accountability, and grit, and you build trust across large enterprise organizations. Most importantly, you drive urgency with your customers by connecting technical pain to business impact.

Location Type: Remote (based out of Chicago) Employment Type: Full-time

Why You’ll Love This Role

Cribl is a serious company that doesn’t take itself too seriously, looking for people who love to get stuff done and laugh along the way. As a remote-first company, we empower our employees to do their best work wherever they are. Cribl is the data engine for IT and Security, trusted by major names in demanding industries to solve pressing data needs.

Responsibilities

• Build and execute a territory plan to consistently exceed quota.
• Own the entire sales cycle—from outbound prospecting to closing strategic, multi-stakeholder deals.
• Develop and nurture relationships across multiple buying centers within large, multinational enterprises.
• Drive opportunities using structured sales methodologies like MEDDICC/MEDDPIC to ensure qualification, process rigor, and forecast accuracy.
• Clearly articulate Cribl’s value proposition from engineers to C-level executives.
• Prioritize customer outcomes and act as a trusted advisor throughout the sales process.
• Collaborate cross-functionally with pre-sales, product, and marketing to win high-value opportunities.
• Occasionally perform duties outside standard working hours, as we are a remote-first team operating across time zones.

Requirements

• 7+ years of success in strategic, complex sales (ideally in high-growth or early-stage companies).
• Proven ability to prospect, build pipeline, and self-source enterprise opportunities.
• Track record of landing and expanding 7-figure deals with Fortune 1000 / G2K accounts.
• Experience navigating long sales cycles with multiple buying centers and executive stakeholders.
• Comfortable selling multi-product, complex tech to various personas—technical and non-technical.
• Familiarity and experience with MEDDICC/MEDDPIC or similar structured sales methodologies.
• Ability to craft and deliver a compelling business case, not just sell on pain or features.
• Success selling un-budgeted solutions and winning based on value—not brand recognition.
• Experience selling through partners or a channel-led motion is a plus.
• A demonstrated commitment to excellence, ownership, and long-term success (2+ years average tenure in recent roles).
• Must be based in the Chicago region with a strong history of selling into this territory.

Compensation & Benefits

• Salary Range: $150,000 – $165,000 USD (dependent on geographic location and candidate qualifications).
• Commission/Incentive Plan: Included.
• Benefits Package: Health, dental, vision, life insurance, paid holidays, PTO, fertility benefits, 401(k), and equity.

Company Information

Cribl is a remote-first company committed to fostering a culture where differences are valued and welcomed. We believe diversity drives innovation, enables better decisions, and inspires positive change. We work together to bring out the best in each other.