Regional Director

Location

Employment Type

Location Type

Department

About this role

We’re hiring a Regional Director to lead our Enterprise AE team in the Midwest, centered on the greater Chicago area. This is a first-line leadership role where you’ll guide a team of talented sellers through complex, multi-stakeholder platform deals with enterprise accounts. The role is critical to Astronomer’s next stage of growth, shaping territory strategy, strengthening team performance, and turning our product strength into repeatable, high-quality revenue.

You’ll be hands-on as a coach and builder: mentoring Enterprise AEs, developing rising talent, and creating a culture where collaboration, resilience, and execution go hand in hand. The ideal candidate has either led enterprise sellers or been a successful enterprise seller themselves in recent years, with experience in high-growth environments and the confidence to navigate multi-threaded, complex evaluations.

Impact in this seat is clear: build a healthy, scalable enterprise motion in the Midwest, raise our win rates, shorten cycles, and set the standard for how we engage enterprise customers.

What you get to do:

• Lead, coach, and develop a high-performing team of Enterprise AEs in the Midwest.
• Shape go-to-market strategy: territory planning, outbound and ABM campaigns, multi-threaded exec alignment, value articulation, and close plans.
• Run a disciplined operating rhythm: 1:1s, pipeline reviews, forecast calls, quarterly business reviews, and consistent coaching moments.
• Design and execute winning strategies for complex platform sales, aligning SE, Product, and Partnerships to accelerate deals.
• Hire top talent, keep a strong bench in play, and partner with Recruiting to build a diverse, inclusive, and high-performing team.
• Drive pipeline standards and forecast accuracy, ensuring coverage, velocity, and reliable outcomes.
• Collaborate with Marketing on targeted programs and with CS on expansion strategies to grow NRR and land-and-expand impact.
• Represent the Midwest business to executive leadership with data-backed insights, risks, and recommendations.

What you bring to the role:

• 2+ years leading first-line Enterprise AE teams with consistent quota attainment.
• Mastery of enterprise methodologies such as MEDDIC, Command of the Message, or similar.
• A builder mindset, with experience thriving in high-growth and smaller company settings, not only large incumbents.
• Strength in executive storytelling, platform selling, and orchestrating technical + business stakeholders.
• A coaching-first leadership style, with a track record of helping sellers grow through feedback, mentorship, and clear standards.
• A data-driven approach to pipeline management and forecasting, with rigor around hygiene, coverage, and stage progression.
• Strong judgment on talent and culture fit, consistently raising the bar while supporting team stability.
• Excellent cross-functional collaboration skills and communication across customers, peers, and executives.

Bonus points if you have:

• Experience selling complex platforms in data, DevOps, infra, or adjacent enterprise SaaS categories.
• A mix of startup or scaleup and larger-company experience, with small-org exposure in the last two roles.
• Experience building regional playbooks, including territory design and ABM co-motion with Marketing.
• A track record of hiring and onboarding diverse enterprise sellers, fostering inclusion, and building a performance-driven, supportive culture.

The estimated total compensation for this role ranges from $390,000 - $420,000, along with an equity component. This range is merely an estimate, and the width of the range reflects willingness to consider candidates with broad prior seniority. Actual compensation may deviate from this range based on skills, experience, and qualifications.

#LI-Hybrid

At Astronomer, we value diversity. We are an equal opportunity employer: we do not discriminate on the basis of race, religion, color, national origin, gender, sexual orientation, age, marital status, veteran status, or disability status. Astronomer is a remote-first company.