SkyLink is building the corporate travel chatbot that allows travelers and arrangers to book and manage travel in enterprise chat channels, Slack & Teams, as if they're speaking to a corporate travel agent. Leveraging the latest in LLMs and generative AI, SkyLink’s workflows can handle simple or complex travel itineraries and changes using natural language. We serve enterprises and Travel Management Companies to save millions in excess corporate travel costs, increase online booking throughput, and delight users who have been stuck with decade old booking tools.

We are backed by Y Combinator, Menlo Ventures, Human Capital, and Fortune 50 CEOs. Our board of advisors includes former CEOs of Global Travel companies.

Why We’re Hiring

Enterprise travel environments are complex—different regions use different GDSs, TMC partners, policies, and user flows. Each new customer needs a tailored deployment. We’re looking for a Deployment Manager to own that process: working directly with enterprise customers, translating their needs into actionable plans, and coordinating with SkyLink engineers to make implementation seamless.

The Role

As our first FDE Manager, you’ll be the primary point of contact for enterprise customers as they roll out SkyLink globally. You’ll act as the connective tissue between clients, engineering, and product—scoping requirements, managing implementation timelines, and guiding deployments from kickoff to go-live.

What You’ll Do

• Own deployment success – Serve as the project owner for customer onboarding, coordinating across stakeholders and ensuring a smooth rollout across regions.
• Manage customer relationships – Act as the trusted technical advisor for client IT and travel teams, building confidence and providing regular updates.
• Translate needs into action – Turn customer requirements into internal implementation plans, and ensure engineers have the clarity they need to execute.
• Lead implementation projects – Manage the technical configuration of GDSs, travel policies, approval flows, and integrations with tools like HRIS and expense systems.
• Support launches & troubleshoot – Help debug deployment blockers and ensure smooth transitions to post-launch support.
• Communicate clearly – Run workshops, demos, and QBRs with customer stakeholders, and coordinate internal updates with product and leadership.

You Might Be a Fit If You

• Have at least 5 years of experience in deployment/project management, solutions engineering, or implementation consulting at a B2B SaaS or travel-tech company.
• Can translate ambiguous customer needs into structured project plans.
• Know how to collaborate cross-functionally with engineers, execs, and external stakeholders.
• Have some technical fluency—you may not write production code daily, but you can read Python, write basic SQL, and hold your own in technical discussions.
• Are energized by problem-solving, customer relationships, and building new systems from scratch.

Nice to Have

• Experience as a manager leading an implementation team.
• Experience with corporate travel tools or working with GDSs, TMCs, or expense platforms.
• Familiarity with Slack/Teams app environments.
• Background in backend or infrastructure engineering (Python, Django, AWS, etc.)

Tech Stack

Python, Django, Celery, Postgres, Redis · React/TypeScript front‑end · AWS, Docker, Terraform · LLM integrations (OpenAI, Anthropic)

Benefits

• Competitive salary & early‑stage equity
• Medical, dental, vision
• New‑hire laptop of your choice
• 401(k) with match
• Unlimited PTO & company recharge days
• Hybrid NYC schedule (Williamsburg HQ)

About the interview

Introduction zoom chat with a cofounder

You’ll meet one of our cofounders to talk about your past projects and experience leading deployments. We’ll discuss your technical background, communication style, and interest in joining an early-stage team.

Project & Technical Interview

We’ll walk through a real-world implementation scenario. You’ll show us how you’d scope a deployment, manage cross-functional dependencies, and navigate technical/organizational challenges with a customer.

• Backend Tech Stack: Python, Django, Celery, Redis, Postgres
• Frontend Tech Stack: React, Typescript
• Infrastructure: AWS, Docker