Cribl

Regional Sales Manager, Chicago (Strategic)

Chicago, Illinois, United States

Not SpecifiedCompensation
Senior (5 to 8 years), Expert & Leadership (9+ years)Experience Level
Full TimeJob Type
UnknownVisa
Data Engine for IT and SecurityIndustries

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.

Skills

Sales
Pipeline Generation
Sales Process
Enterprise Sales
MEDDICC
MEDDPIC
Relationship Building
Territory Planning
Outbound Prospecting
Closing Deals

Cribl

Data observability solutions for tech businesses

About Cribl

Cribl operates in the data observability market, helping tech businesses monitor, analyze, and visualize their data for better operational and security insights. The company offers two main products: Cribl Stream and Cribl Edge. Cribl Stream enables businesses to efficiently route and transform logs and metrics, either on their own infrastructure or through cloud services, ensuring timely data delivery. Cribl Edge focuses on collecting and processing real-time observability data from edge devices, which can then be sent to Cribl Stream or other destinations. Cribl distinguishes itself by integrating seamlessly with platforms like Office 365 and Microsoft Azure, allowing clients to enhance their data management capabilities. The company's goal is to create effective data ecosystems that empower organizations to make sense of their data.

San Francisco, CaliforniaHeadquarters
2018Year Founded
$576.3MTotal Funding
SERIES_ECompany Stage
Data & Analytics, Enterprise SoftwareIndustries
501-1,000Employees

Benefits

Competitive Salary
Stock Options
Medical, dental, and vision insurance
Flexible spending account (FSA)
401(k) plan offered (US)
Parental Leave
Professional Development and Career Growth
Generous Vacation and Holiday Policy, including 2 Floating Holidays for holidays you observe
Employee Resource Groups that reflect our values driven company culture

Risks

Emerging data observability startups could threaten Cribl's market share with competitive pricing.
Rapid AI advancements may outpace Cribl's offerings if not updated timely.
Economic downturns could impact Cribl's ability to maintain its high valuation.

Differentiation

Cribl offers unique data routing and transformation with Cribl Stream and Cribl Edge.
The company integrates seamlessly with major platforms like Office 365 and Microsoft Azure.
Cribl's focus on real-time data processing sets it apart in the data observability market.

Upsides

Cribl raised $319M in Series E funding, boosting its valuation to $3.5 billion.
The rise of multi-cloud strategies enhances Cribl's integration capabilities across cloud environments.
Increased demand for edge computing solutions positions Cribl Edge for significant growth.

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