Remote Head of Sales

Location: US (New York or East Coast) - Remote

Type: Full-time

About Kestra

Kestra is the universal orchestration platform — open source, declarative, and designed to orchestrate data pipelines, IT automation, business workflows, and AI/agentic systems.

Kestra is the fastest-growing open-source orchestration project in the world — close to 30,000 GitHub stars, hundreds of contributors, and a global community scaling rapidly across engineering, data, and IT teams.

Following a $25M Series A, we're accelerating our US expansion while already operating at scale in Europe.

Why Kestra

Every organization runs on workflows — thousands of them, mission-critical, often invisible until they fail.

Most of these workflows are trapped in legacy orchestration platforms built 15 or 20 years ago. These systems cost millions to maintain, take months to modify, create deep vendor lock-in, and were designed for a world that no longer exists. At the same time, the rise of cloud, microservices, AI agents, and multi-team architectures has created an explosion of operational complexity that these platforms were never built to handle.

Kestra was created to solve this problem. Born from a real failure — a large-scale Airflow deployment that could not meet the requirements of a 30,000-employee enterprise — we built an open-source orchestration platform that any engineer can adopt in minutes, that replaces seven-figure legacy systems in days, and that provides full visibility and control over every workflow across the organization.

We are trusted by Bloomberg, JPMorgan Chase, Deutsche Telekom, Toyota, BHP, Crédit Agricole, and FILA — all acquired without outbound sales in their respective markets.

Our ambition is to become the orchestration standard for every enterprise. Not a point solution. Not a dev tool. The execution backbone — one engine, every use case, every team.

We are not riding a hype cycle. We are solving a structural problem that grows with every layer of complexity the industry adds. Building Kestra requires persistence, adaptation, and rigorous execution over time. We are looking for people who think the same way.

The Role

We're looking for a Head of Sales to own the global revenue number, build the team, and define the motion that makes growth repeatable. Based in the US, you will lead Kestra's commercial expansion globally — starting with the US market while working in close coordination with the European team.

This is a builder-manager role. You will design the sales process, lead and grow an existing team of Sales Leads and Solution Engineers, and create the conditions for the team to perform consistently. You will be present on strategic deals as an executive sponsor — providing executive alignment, navigating procurement, and unlocking stalled cycles — but you are not the primary closer. Your job is to build a machine that scales, not to be the machine yourself.

You report directly to the CEO and work closely with Customer Operations, Product, and Marketing/PMM.

The GTM Context

Kestra starts where engineers live — open source, self-hosted, community-adopted. Thousands of organizations are already running Kestra in production before they ever talk to sales. The Head of Sales needs to understand how to build an enterprise motion on top of that reality: converting community signal into pipeline, working with technical champions, and building a compelling enterprise narrative without alienating the developer base.

This is the core challenge of the role, and the thing that makes it different from a standard enterprise SaaS sales leadership position. Experience with OSS-led or PLG-to-enterprise motions — at companies like Confluent, HashiCorp, Grafana, dbt Labs, or equivalent — is a strong differentiator.

What You'll Do

The Head of Sales is the architect of a scalable sales system. You move from selling to organizing and optimizing a system that sells at scale — defining the strategy, building repeatable processes, and assembling the team. Your primary objective is to make revenue growth predictable and data-driven.

Own the number — You own global ARR. That means owning the pipeline generation strategy, forecast accuracy, and the commercial outcomes of the team. You are the executive presence on strategic deals, not the primary closer.

Build and lead the team — You lead an existing team of AEs, Sales Leads, and SEs, and grow it deliberately. You set the bar for coaching culture, hiring standards, and execution discipline.

Define the motion — You design the playbooks, qualification framework, POC policy, and sales process that make results repeatable. You turn what works into something others can run.

Align the go-to-market — You work closely with Marketing on pipeline generation, positioning, and proof content. You partner with Customer Operations on expansion and NRR. You feed structured market signal back to Product without turning every deal into a roadmap request.

What We're Looking For

• Proven track record building and scaling a B2B enterprise sales team in developer tools, infrastructure, data/AI tooling, or open-source software

• Experience with OSS-led or PLG-to-enterprise GTM motions — you understand how to turn a technical community into a sales pipeline

• Has operated in a Series A/B environment and knows what "builder" actually means in practice: no inherited playbook, no mature SDR team, no established brand in the market

• Comfortable with complex enterprise sales: security reviews, procurement cycles, multi-stakeholder alignment, long deal cycles

• Able to define a clear wedge for a general-purpose platform and build a playbook others can run and repeat

• High standards, low ego — coaching-oriented, execution-focused, and honest about pipeline reality

Bonus points

• Background in orchestration, infrastructure automation, or workflow management

• Familiarity with technical buyers and developer communities

• Experience selling into IT, platform engineering, or data engineering personas

What You'll Be Measured On

• Global team ARR / bookings and attainment vs. target

• Pipeline coverage, generation rate, and SQL → Close conversion

• Win rate, average cycle length, ACV

• Forecast accuracy

• Rep ramp time and productivity per rep

• NRR / avoidable churn (shared with CS)

What You Get

• Real ownership in a globally distributed, technical team

• Direct line to the CEO and full visibility on company strategy

• A product already running mission-critical workloads at Fortune 500 companies

• Competitive compensation, equity, and health insurance

Location & Travel

Base: US (East Coast preferred), fully remote. Regular travel to customers, industry events, and team offsites. Close coordination with the European team across time zones.