Top Tech Jobs & Startup Jobs in Boston, MA

The Head of Leadership Search will lead global leadership hiring, establish hiring strategies, manage an executive search team, and partner with executive leadership.

Serve as a technical expert for Datadog’s Service Management products, advising enterprise customers and Field teams on incident response, on-call, event correlation, workflow automation, and App Builder architectures. Build proofs of concept, small-scale deployments, reusable technical collateral, and best practices. Provide product feedback based on customer engagements to influence roadmap development. The role requires engineering expertise, production incident response or automation experience, observability knowledge, coding ability, consultative customer skills, and travel up to 40%.

Drive product attachment and adoption for large enterprise customers through relationship management, onboarding, usage analysis, renewal risk mitigation, and cross-functional collaboration. Act as trusted advisor aligning customers' technical and business objectives to Datadog's observability and security offerings.

Manage semi-monthly US payroll for 3,000+ employees using Workday; process hires/terminations/status changes, garnishments, 401(k) feeds, equity transactions, and resolve payroll discrepancies. Support Canada and Latin America administratively, collaborate with Finance, SOX and 401(k) auditors, maintain payroll records, run audits, and respond to payroll/tax inquiries.

Sets application security direction and standards across engineering teams. Builds scalable security tooling, automation, and observability; leads threat modeling, risk assessments, code reviews, and multi-team remediation. Develops strategies for AI-powered systems and agentic development risks, API security, and software supply chain security. Partners with engineering and security teams, prioritizes investments, communicates risk to leadership, and mentors AppSec engineers.

Prospect and qualify potential customers through outbound cold calling and email outreach. Schedule discovery meetings, develop new-business acquisition strategies, and identify customer needs using Datadog’s sales methodology. Collaborate with internal teams while helping technology innovators understand Datadog’s value in digital transformation and cloud migration. The role offers sales training, mentorship, professional development, and career growth opportunities.

Lead product vision and roadmap for a unified fleet and lifecycle management platform that manages observability agents and collectors across hosts and Kubernetes. Coordinate cross-functional engineering teams to expand supported components, define "managed" behaviors, sequence rollout, set success metrics, and represent customer needs for both human operators and AI agents. Build business cases, validate with customers, and communicate trade-offs to stakeholders.

Partner with sales to qualify and close opportunities by delivering technical presentations, demos, and POCs. Support onboarding, resolve customer issues, escalate bugs, gather product feedback, and collaborate with product and cross-functional teams. Hybrid role based in Boston with some travel.

Serve as a trusted technical advisor to enterprise customers, driving product adoption, providing hands-on IT operations guidance, performing environment analysis, conducting business reviews, collaborating with product and engineering teams, and improving best practices to maximize Datadog value.

Leads regional Enterprise Sales Engineering through frontline leader management, strategic deal execution, technical customer engagement, capacity planning, forecasting, hiring, coaching, and operational excellence. Partners with Sales, Product, Marketing, Enablement, and Support to scale go-to-market execution and customer outcomes. The role requires deep experience in sales engineering leadership, cloud and observability technologies, security, cross-functional influence, executive communication, sales methodologies, and AI tooling. Travel is required as needed.