Regional Sales Manager, Chicago (Strategic)

Remote - Chicago, Illinois

Cribl does differently. 

What does that mean? It means we are a serious company that doesn’t take itself too seriously; and we’re looking for people who love to get stuff done, and laugh a bit along the way. We’re growing rapidly - looking for collaborative, curious, and motivated team members who are passionate about putting customers first. As a remote-first company we believe in empowering our employees to do their best work, wherever they are. 

As the data engine for IT and Security many of the biggest names in the most demanding industries trust Cribl to solve their most pressing data needs. Ready to do the best work of your career? Join the herd and unlock your opportunity.

Why You’ll Love This Role

We are 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.

Please note, this is a remote position based out of Chicago. We are looking for candidates based in the region, with a strong history of selling into this territory.


As An Active Member Of Our Team, You Will…

  • Build and execute a territory plan to consistently exceed quota
  • Own your 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 your standard working hours, as we are a remote-first team operating across time zones


If You’ve Got It – We Want It

  • 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)


Salary Range ($150k–165k USD)
The salary for this role depends on geographic location and the candidate’s qualifications. In addition to a competitive base salary, Cribl offers a robust benefits package including health, dental, vision, life insurance, paid holidays, PTO, fertility benefits, 401(k), and equity. This role also includes a commission/incentive plan.

 

Bring Your Whole Self
Diversity drives innovation, enables better decisions to support our customers, and inspires change for the better. We’re building a culture where differences are valued and welcomed, and we work together to bring out the best in each other. All qualified applicants will receive consideration for employment without regard to race, color, religion, sex, sexual orientation, gender identity, national origin, or any other applicable legally protected characteristics in the location in which the candidate is applying.

Interested in joining the Cribl herd? Learn more about the smartest, funniest, most passionate goats you’ll ever meet at cribl.io/about-us. 

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