Regional Sales Manager, Chicago (Strategic)

Company shown to members 🔒 · Remote · US only

US only7+ years required$160K–175K/yrPublished 7 October 2026Looks fresh

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First recorded by Psst: 12 October 2026. Your first 3 jobs are free to apply to (the first right away, 2 more with your email). After that, the company and the apply link are for Psst members, from $4.99 for 7 days.

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The 20-second read

Experience
7+ years required
Where you can live
US only
Skills and tools
forecasting

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Job details

Where you can work
United States
Employment type
Not stated by the employer
Advertised pay
$160K–175K/yr
Experience
7+ years required
Employer publication date
7 October 2026
First recorded by Psst
12 October 2026
Last checked at the source
10 November 2026

About the job

Join the company that’s building the telemetry infrastructure for the AI era. At the company, we partner with IT and Security teams at many of the world’s biggest enterprises, including half of the Fortune 100, to bridge the gap between AI ambition and infrastructure reality. As the AI Platform for Telemetry, we give customers the choice, control, and flexibility to manage and analyze telemetry for both humans and agents, so they can build what’s next.

We’re one of the fastest‑growing private companies and a leading player in a massive, fast‑moving market. With a global workforce, we’re remote‑first and grounded in a simple idea: software is a people business. The company is the place where curious, collaborative people can do their best work, grow fast, and bring their full selves to the herd.

Why You’ll Love This Role

We are seeking a Strategic Sales Representative who is ambitious, adaptable, and enthusiastic. A successful Strategic Sales Rep at the company will clearly articulate our value proposition and execute on proven sales processes. This rep will come with accountability and ownership, specifically in meeting leading indicators. Most importantly, we put our customers first, always. We are looking for a rep who will do just that. The ideal candidate will come with expertise in creating customer centric solutions, and be able to build strong enduring relationships with our customers.

Please note, this is a remote position based out of Chicago . We are looking for candidates to live local to the territory, and with a track record of successfully selling into the region.

As An Active Member Of Our Team, You Will…

  • Develop a business plan to overachieve sales goals
  • Manage and maintain the entire sales ecosystem from generating leads through closing
  • Help customers understand the value of the company during the sales process
  • Articulate our value proposition up and down the organization, from engineer up to CxO
  • Forecasting predictably and hitting sales targets
  • We are a remote-first company and work happens across many time-zones – you may be required to occasionally perform duties outside your standard working hours

If You’ve Got It - We Want It

  • 7+ years of Strategic Security Sales experience selling into Fortune Level Organizations calling on Security (SIEM & Observability) & IT Personsas (CISCO/CIO’s)
  • Experience working with at least one earlier stage start-up organization <1000 employees or has demonstrated entrepreneurial skills throughout their career
  • Proven Track record of landing and expanding 7 figure deals
  • Success selling to G2K companies, and developed at least one new logo from scratch
  • Experience selling through a channel led motion
  • Able to create demand in a territory and selling un-budgeted solutions
  • Background using MEDDIC

#LI-SP1

#LI-Remote

The salary for this role is dependent on geographic location and will be based on the individual candidate's job-related knowledge, skills, and experience.

In addition to base salary, for sales and some sales-adjacent roles, employees are eligible to earn incentive compensation (commission). For all other roles, employees are eligible to participate in the company Corporate Bonus Program.

In addition to a competitive salary, the company also offers a generous benefits package which includes health, dental, vision, short-term disability, and life insurance, paid holidays and paid time off, a fertility treatment benefit, 401(k), and equity.

Base Salary Range

$160,000 — $175,000 USD

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 company herd? Learn more about the smartest, funniest, most passionate goats you’ll ever meet at the company .

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