Outbound Marketing & Automation Specialist (Mid-Market & Enterprise)

We are seeking an innovative, highly technical Outbound Marketing & Automation Specialist to own our outbound lead generation motion. Your primary objective will be to connect with and book meetings with HR Leaders at mid-market and enterprise companies (500-5000+ employees).

We believe in a lean, highly customized tech stack. Instead of relying on expensive, off-the-shelf outreach tools, you will use your expertise in Make.com/Zapier and Claude to engineer bespoke automation workflows. If you excel at prompt engineering, deeply understand email deliverability, and know how to seamlessly hand off qualified leads to Sales, we want you in the driver's seat of our pipeline generation.

You will be working remotely as an independent contractor.

Moving to a new country is as easy as booking a flight!

Jobbatical is using AI and automation to make the employee visa and relocation process faster and less expensive, so businesses can hire whoever they want, from wherever they want. Jobbatical today is the go-to immigration and relocation partner for tech startups and traditional companies alike. Our team is on a mission to make moving to a new country as easy as booking a flight. The best way to do that is by making the hardest part of relocating to another country – immigration – ridiculously easy. 

We help clients like N26, Pipedrive, and Travelperk to relocate people to 30+ countries and are backed by some of the best investors in the world including Union Square Ventures, Inventure, Karma VC, Swiss Post Ventures, et al.

Your key responsibilities

• Own the Enterprise HR Outbound Motion: Design and lead outbound campaigns targeting HR executives and decision-makers in companies with 500-5000 employees, ensuring messaging is empathetic, highly relevant, and value-driven.

• Lean Workflow Automation: Act as the chief architect of our outbound engine. Use Make.com and Zapier to connect data sources, orchestrate multi-channel touches (Email/LinkedIn), and run campaigns without relying on bloated software stacks.

• Advanced Prompt Engineering: Masterfully utilize Claude (and other LLMs when necessary) via API to generate hyper-personalized, context-aware, and natural-sounding outreach at scale.

• Email Infrastructure & Deliverability: Take complete ownership of our sender reputation. Manage domain setup, inbox warming, and compliance to ensure our carefully crafted messages land in the primary inbox, not the spam folder.

• CRM Integration & Sales Handoff: Build automated routing systems to push engaged leads seamlessly into our CRM, providing the Sales team with full context for a smooth handoff.

• KPI Ownership: Treat the outbound motion like a science.  You will own and be measured against core metrics:

  • Primary:  Pipeline Generated

  • Secondary : Open Rates, Reply Rates and Meetings Booked

What helps you to succeed in this role

• Proven, hands-on experience building complex, reliable workflows from scratch using Make.com and/or Zapier. You should be highly comfortable working with Webhooks and APIs.

• Deep understanding of how to prompt LLMs - specifically Claude - to write non-robotic, highly persuasive B2B copy.

• Experience selling into or marketing to Mid-Market/Enterprise HR leaders is a massive plus. You understand their pain points and how to capture their attention.

• Strong understanding of technical email infrastructure (SPF, DKIM, DMARC) and the mechanics of safe, high-volume sending.

• Ability to run A/B tests, analyze campaign data, and pivot strategies based on hard metrics rather than gut feelings.

• A builder's mentality. You prefer to construct a custom, elegant solution with APIs and automation rather than just requesting budget for a new tool.

Who you are

• You "start with why" and define the problem before jumping into a solution.

• You are an early adopter of AI, using it to 10x your output without losing quality.

• You naturally consider security and safety as a core part of the process.

• You are a team player who knows we succeed or fail together.

Why Join Jobbatical?

We are a diverse and growing team of 40 people, currently delivering in-house immigration across Europe.

Innovative Environment: Be part of a forward-thinking team that's redefining global mobility Growth Opportunities: Expand your skills and grow with a company that's scaling rapidly Impactful Work: Play a key role in shaping global mobility processes and contributing to our success

You can learn more about the company and the team here: https://jobbatical.com/about 

Our offer to you includes

• Solid compensation package
• YOLO days on top of generous annual holiday days
• Any hardware you need: Mac, headphones, etc
• Flexible working time
• Possibility to work among passionate professionals who change the world of immigration
• A lot of international challenges to help you grow and thrive

We’re an equal-opportunity employer that values diversity and positively encourage applications from suitably qualified and eligible candidates regardless of race, religion, sex, national origin, gender, sexual orientation, age, marital status, veteran status, disability status, pregnancy or maternity or other applicable legally protected characteristics.