We are not here to blend in. We are here to redefine what observability means and how it is delivered.
groundcover has built a radically different approach to cloud-native observability that competitors can’t match. As a part of our Sales team, you won’t just sell a product, you’ll help reshape the narrative of the category so the world understands why groundcover is the clear, modern choice for engineering and operations teams.
About groundcover
groundcover is a fast-growing Series B startup delivering the industry’s most modern observability platform for cloud-native environments. Powered by BYOC and eBPF and designed for Kubernetes from day one, our platform delivers full stack observability with dramatically lower cost, operational overhead, and complexity.
As systems evolve toward AI powered services and LLM based applications, observability must evolve with them. groundcover is built for this reality, enabling teams to understand performance, reliability, and behavior across microservices, infrastructure, and AI workloads.
We are looking for our first Regional Sales Director to join our Boston Office (3 days a week onsite)
What You’ll Do
- Lead & Develop: Mentor, coach, and motivate a team of Account Executives. Support hiring, onboarding, and ongoing development.
- Drive Sales: Own the strategy and execution for your region. Track pipeline, forecast revenue, and ensure targets are met.
- Customer Engagement: Build strong relationships with key clients. Support AEs in closing complex deals.
- Market Insight: Stay ahead of market trends and competitive landscape to inform strategy.
- Collaboration: Partner with Marketing, Product, and Customer Success teams to amplify impact.
Who You Are
- 5+ years in sales, with at least 2 years managing a team.
- Proven track record of driving team revenue and hitting sales targets.
- Experience in B2D, SaaS, or developer-focused tech preferred.
- Strong communication, coaching, and leadership skills.
- Analytical and data-driven with experience leveraging CRM tools.
- Comfortable in a fast-paced, high-growth environment.
Similar Jobs
What you need to know about the Chicago Tech Scene
Key Facts About Chicago Tech
- Number of Tech Workers: 245,800; 5.2% of overall workforce (2024 CompTIA survey)
- Major Tech Employers: McDonald’s, John Deere, Boeing, Morningstar
- Key Industries: Artificial intelligence, biotechnology, fintech, software, logistics technology
- Funding Landscape: $2.5 billion in venture capital funding in 2024 (Pitchbook)
- Notable Investors: Pritzker Group Venture Capital, Arch Venture Partners, MATH Venture Partners, Jump Capital, Hyde Park Venture Partners
- Research Centers and Universities: Northwestern University, University of Chicago, University of Illinois Urbana-Champaign, Illinois Institute of Technology, Argonne National Laboratory, Fermi National Accelerator Laboratory
