Regional Director of Sales - Mid-Market

Regional Director of Sales — Boston

Series B · Cloud-Native Observability · Boston, MA (Hybrid)

The Opportunity

We are a fast-growing Series B company redefining what observability means for cloud-native environments. Our platform is built for Kubernetes from the ground up — powered by eBPF and BYOC architecture — and it delivers full-stack observability at dramatically lower cost and complexity than anything else in the market.

We are hiring our first Regional Sales Director in Boston. This is not a "manage the process" role. You will build the team, install the structure, and own the region.

What You Will Do

Lead a Team of Account Executives

• Inherit a group of high-performing AEs and build the team from there — you will hire, onboard, and develop the people around you
• Coach deals, run pipeline reviews, and be in the trenches with your reps on the complex, multi-threaded cycles that define this space
• Create the structure and processes that do not yet exist — this company has grown fast without a management layer, and you are here to change that

Own the Region

• Accountable for pipeline generation, forecast accuracy, and revenue target attainment across the Boston team
• Build deep relationships with key enterprise accounts and show up when it matters to help your AEs close
• Stay close to the developer and engineering buyer — understand the ecosystem, the workflows, and the competitive landscape well enough to coach your team through any situation

Partner Cross-Functionally

• Work closely with Marketing, Product, and Customer Success to sharpen the message and amplify what is working
• Feed real market and competitive intelligence back into the business to inform how we evolve the GTM motion

What We Are Looking For

• 5 to 7 years of closing experience in B2B SaaS or developer-focused technology — you have done this, not just managed people who have done it
• At least 1 to 2 years of first-line sales management — you know how to coach and develop sellers, not just sell yourself
• Experience in DevTools, infrastructure, observability, or security — you can speak credibly to developers, DevOps teams, and engineering leaders without needing a script
• Comfortable with complex, technical sales cycles — multi-threaded deals with $50K to $750K in value that require patience, strategy, and strong executive engagement
• Builder mentality — you are energized by ambiguity, you create structure where there is none, and you do not wait to be told what to build next
• High energy, in-office culture fit — this is a hands-on, collaborative environment and you will be in the Boston office three days a week
• Analytical and data-driven — you live in your CRM, you trust the numbers, and you hold your team to the same standard

Why This Role

• You are joining at an inflection point — the company just raised its Series B and is building its management layer for the first time. The people coming in now will define how this scales.
• You will build your own team from scratch — real autonomy over hiring, structure, and process. No inherited playbook to follow.
• The product is genuinely differentiated — eBPF-powered, BYOC architecture, built for Kubernetes from day one. It wins in POVs against larger, legacy competitors.
• The trajectory is real — the customer list speaks for itself and the momentum is there. This is not a bet on a future that has not arrived.

Compensation

OTE: up to $350K (base variable, 50/50 split)

Equity: included

Location: Boston, MA — hybrid, 3 days per week in office

If you have built and led technical sales teams in the developer or infrastructure space and you are looking for a role where you actually own something — let's talk.