Regional Vice President, Central | Enterprise Observability & AIOps Sales

Location: Chicago, Dallas, Minnesota, or Ohio
Compensation: $420,000 OTE, 50/50 split
Team: 5 Enterprise Sales Reps

The Opportunity

A high-performing enterprise sales region is looking for its next leader.

This Regional Vice President will inherit a 5-person enterprise sales team across the Central U.S. , including 3 reps with 4+ years of tenure and 2 newer team members.

This is not a turnaround assignment.

The Central region has been the #1 performing region in 2 of the last 3 years , giving the incoming RVP an established team, experienced sellers, and a strong foundation to build on.

The opportunity is to take a good situation and make it even better.

The company operates in AIOps / Event Intelligence , a specialized area within the broader observability ecosystem. Its technology uses machine learning to correlate massive volumes of IT alerts from fragmented monitoring environments into a much smaller number of actionable incidents.

Rather than replacing an enterprise's existing monitoring stack, the platform sits above it, helping complex organizations reduce noise, understand incidents faster, and improve IT operations.

For a sales leader coming from observability, APM, infrastructure monitoring, or an adjacent technical market, this is an opportunity to lead an established enterprise team while staying close to customers, reps, and strategic deals.

What You'll Own

You'll lead, coach, and develop 5 enterprise sellers across the Central region.

This is a hands-on leadership position. The expectation is not to manage exclusively through dashboards, forecasts, and pipeline calls.

You'll be expected to:

• Get directly involved in strategic enterprise opportunities
• Coach reps individually based on their strengths and development areas
• Raise the performance of the team collectively
• Help reps identify and develop genuine Champions
• Ensure customer Pain is understood and connected to business impact
• Strengthen deal strategy and execution throughout complex sales cycles
• Maintain high standards around qualification and forecasting
• Partner effectively with Sales Engineering and other internal teams
• Push experienced reps to continue improving while accelerating newer team members

The core question for this hire is simple:

How do you take an already successful enterprise sales organization and raise its ceiling?

What We're Looking For

The strongest candidates will bring:

• 3-5+ years of sales leadership experience , with approximately 7+ years likely to be particularly competitive
• Meaningful experience in observability or a closely adjacent technology market
• A track record selling and leading within complex enterprise environments
• Experience operating at a smaller or mid-sized technology company , rather than a career spent exclusively inside very large technology organizations
• A demonstrated willingness to get actively involved in deals alongside reps
• Strong individual and team coaching ability
• Experience with MEDDPICC and/or Command of the Message
• Strong understanding of Champions and Pain within complex enterprise sales processes
• A clearly documented 5-year performance history , including quota attainment
• Evidence of improving seller performance rather than simply managing established teams

Relevant backgrounds may include:

Observability, AIOps, APM, Event Intelligence, infrastructure monitoring, cloud monitoring, IT operations, incident management, telemetry, log management, and related enterprise infrastructure software.

Experience from organizations in the Datadog, Dynatrace, Splunk, New Relic, Elastic, Moogsoft, and similar ecosystems may translate particularly well.

Candidates whose backgrounds are exclusively within large "big box" technology companies, VARs, IBM, or ServiceNow are unlikely to align with what the team needs.

The Team You're Inheriting

You'll manage 5 enterprise sales reps :

• 3 have been with the organization for 4+ years
• 2 are newer to the team
• The region has finished as the company's top-performing region in 2 of the last 3 years

You're walking into a strong situation.

That also raises the bar for leadership.

The team needs someone who can earn credibility with experienced enterprise sellers, contribute meaningfully to deals from day 1, coach different personalities and experience levels, and continue pushing successful reps to improve.

Compensation & Benefits

$420,000 OTE with a 50/50 split

Approximately:

$210,000 base salary
$210,000 variable compensation

The package also includes:

• Full health benefits
• Generous PTO
• 401(k) match
• RSUs

Interview Process

The interview process is expected to include conversations with:

• Area VP
• VP of Sales
• CRO
• Sales Engineering leadership, if the candidate would like that additional conversation

Why This Role?

Many RVP opportunities begin with a broken territory, significant rep turnover, or a team that needs to be rebuilt.

This one doesn't.

You're inheriting a region that has been #1 in 2 of the past 3 years , including experienced sellers with meaningful tenure.

The challenge is different: preserve what's working, identify where the team can become better, and personally help enterprise sellers win more complex opportunities.

For a hands-on sales leader with credibility in observability and a history of developing enterprise sellers, this is an opportunity to step into an established region with significant responsibility, strong compensation, and equity participation.