Astronomer-posted 3 months ago
$390,000 - $420,000/Yr
Full-time • Manager
Hybrid • Chicago, IL
251-500 employees
Publishing Industries

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.

  • 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.
  • 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.
  • 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.
  • Estimated total compensation for this role ranges from $390,000 - $420,000, along with an equity component.
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