Regional Sales Director, Midwest

About the role

This opportunity centers on leading a specialized sales function within a high-growth technology organization. The position focuses on directing sales operations for a defined geographic region. Success in this role requires a combination of strategic planning and hands-on leadership.

Cribl operates at the intersection of telemetry and AI, providing infrastructure for major global enterprises. The company serves a significant portion of the Fortune 100, emphasizing a remote-first work model. This role reports to the VP of Sales and contributes directly to the go-to-market strategy.

Position Overview

You will own the entire sales cycle for a specific region, driving both new customer acquisition and existing account expansion. Your primary responsibility is to lead a small, focused team of sales professionals. You will set the vision and direction for this group, ensuring alignment with broader company objectives.

The role involves coaching team members to handle complex sales scenarios. You will be expected to exceed demanding quarterly and annual performance targets. A critical part of this position is architecting and executing a business plan that identifies new opportunities and grows current accounts.

You will manage the full spectrum of the sales ecosystem, from initial lead generation to final deal closure. This includes navigating long and intricate sales cycles typical of enterprise technology. You will work closely with a proven leadership team to shape the overall go-to-market approach.

This is a remote position based in the Midwest region. The role requires occasional work outside standard hours to accommodate global time zones. The company operates across multiple time zones, so consistent sales momentum is essential.

Core Requirements

Candidates must possess a minimum of five years of experience leading strategic sales teams. A proven track record of overachieving annual sales goals is mandatory. Experience managing sales teams that engage with security channel partners is highly valued.

You must be adept at handling complex sales cycles and have deep experience with SaaS sales models. This includes familiarity with cloud, logs, metrics, and IT operations concepts. A history of selling large-scale deals to Fortune 1000 companies is required.

Proficiency with the MEDDIC sales methodology is a strict requirement. You must have direct experience in developing sales pipelines and opening new accounts. The ability to operate effectively in a remote-first environment is non-negotiable.

Preferred Qualifications

While not mandatory, experience within cloud, security, or machine learning domains is a significant advantage. These specific knowledge areas provide a deeper understanding of the customer's technical environment. Such a background allows for more effective communication with technical stakeholders.

Compensation and Benefits

The base salary for this position is competitive and falls within a specific range. The total compensation package includes base salary and potential incentive compensation. Employees are eligible for the corporate bonus program, in addition to comprehensive benefits. These benefits include health, dental, and vision insurance, as well as paid time off and holidays.

What you'll do

• Architect and execute a business plan that identifies new opportunities and grows current accounts within the designated Midwest territory.
• Lead, coach, and develop a small, focused team of sales professionals, providing guidance to navigate complex enterprise sales scenarios.
• Own the entire sales cycle for the region, driving new customer acquisition and maximizing expansion within existing accounts.
• Set the vision and direction for the sales team, ensuring strict alignment with the broader company objectives and go-to-market strategy.
• Exceed demanding quarterly and annual performance targets through consistent pipeline generation and meticulous deal execution.
• Manage the full spectrum of the sales ecosystem, from initial lead generation to final deal closure, ensuring no opportunities fall through the cracks.
• Navigate long and intricate sales cycles typical of enterprise technology, demonstrating resilience and strategic persistence.
• Utilize the MEDDIC sales methodology to structure complex deals, identify stakeholders, and secure stakeholder buy-in.
• Develop and maintain deep relationships with key decision-makers, influencing outcomes for large-scale deals within the Fortune 1000.
• Work closely with the leadership team to analyze market trends, refine the positioning, and adapt the sales approach for maximum impact.
• Operate effectively within a remote-first environment, managing your schedule and communication to maintain consistent sales momentum across multiple time zones.
• Occasionally adjust working hours to accommodate global time zones, ensuring critical meetings and opportunities are secured without delay.
• Leverage data and insights to prioritize high-value opportunities, forecast accurately, and drive predictable revenue growth for the region.
• Act as a strategic partner to customers, helping them solve critical challenges related to telemetry, logs, metrics, and IT operations through the Cribl platform.
• Build and maintain a robust sales pipeline, ensuring a constant flow of qualified leads and a healthy conversion rate at every stage.

Requirements

• Must possess a minimum of five years of experience leading strategic sales teams in a technology environment.
• Must have a proven track record of overachieving annual sales goals and consistently exceeding quotas.
• Must have direct experience managing sales teams that engage with security channel partners and navigate partner-led sales motions.
• Must be adept at handling complex sales cycles that involve multiple stakeholders and lengthy decision-making processes.
• Must possess deep experience with SaaS sales models and a comprehensive understanding of cloud infrastructure concepts.
• Must have familiarity with logs, metrics, and IT operations concepts to effectively communicate value to technical audiences.
• Must have a history of selling large-scale, complex deals to Fortune 1000 companies and enterprise-level organizations.
• Must be proficient in the MEDDIC sales methodology, applying its principles to structure, validate, and win complex opportunities.
• Must have direct experience developing sales pipelines from scratch and opening new enterprise accounts in a scalable manner.
• Must demonstrate the ability to operate effectively in a remote-first work environment, thriving without direct supervision.
• Must be comfortable using CRM tools to maintain accurate forecasting, report progress, and manage key account strategies.
• Must possess strong written and verbal communication skills, capable of articulating complex technical concepts to diverse audiences.
• Must be a self-motivated individual with a high degree of integrity, resilience, and a relentless focus on achieving results.
• Must be legally authorized to work in the United States without sponsorship requirements for this position.

Nice to have

• While not mandatory, prior experience within cloud, security, or machine learning domains is a significant advantage.
• Experience selling to Fortune 1000 companies in a direct or indirect capacity is highly valued.
• Familiarity with observability pipelines, logging platforms, and modern data stack concepts provides a distinct edge in this role.
• Understanding of AI-driven security operations and log analysis enhances the ability to engage technical stakeholders.
• Previous experience coaching and developing high-performing sales teams is a preferred qualification.
• Knowledge of the security channel partner ecosystem and how to leverage it for growth is advantageous.

Practical notes

• This is a remote position based in the Midwest region of the United States.
• The role reports directly to the Vice President of Sales.
• The position requires occasional work outside standard hours to accommodate global time zones.
• The company operates across multiple time zones, necessitating consistent sales momentum and availability for critical meetings.
• Employment is contingent upon the successful completion of background checks and verification of employment eligibility in the United States.