Your missionYour goal is to own the entire expansion engine for our existing customer base. This isn't about writing marketing copy; it’s about the sophisticated execution of commercial transitions. You will identify exactly who is ready for an upgrade, design the logic for their specific contract configuration, and automate the process so that "Expansion" happens at scale, without manual friction.You are the bridge between the Commercial Value Story and the Hard Data of our contract base.What You’ll Do
• Architect Expansion Campaigns: Own the end-to-end execution of price increases, basket transitions, and upgrades
• ARR upside analysis: Identify baselines within the installed base that can be targeted for a price increase, upsell- or cross-sell campaign based on their contract specifics. Use SQL, python and postgres as technical tools, and be comfortable with a complexe landscape of legacy contracts, varying legal environments, multiple currencies, diverse product baskets
• Automate the Lifecycle: Design and implement the logic that moves a customer from a "campaign communication" to an "automated contract renewal." You'll ensure these changes find their way into our systems without breaking the renewal process
• Design Self-Service Paths: Build the technical and logical guardrails that allow customers to expand their own contracts (upsells, cross sells) via self-service, ensuring the data syncs perfectly with our financial reporting
• Partner with BI & Finance: Serve as the technical counterpart to the BI team. You’ll ensure that every expansion action is correctly reflected in Booked ARR reporting and overall data structures
• Own the System Evolution: We currently host our data in Odoo, but a migration is on the horizon. You will be a key stakeholder in designing the data architecture for our future target system
• Measure Everything: You aren't finished until the report is in. You’ll support delivering KPIs like Churn Analysis, Expansion Targets, and Email Hit Rates, providing a clear ROI on every campaign

Your profile
• The Technical Core: You are highly proficient in SQL and Postgres. You can use Python to automate data workflows and manipulate complex data sets
• The Data Mindset: You have a profound understanding of contract and sales order data structures. You "see" the connection between a legal clause and a data field
• Commercial Sharpness: You understand the "Value Story." You know how to translate a technical upgrade into a loyalty-driving customer communication
• Hands-on Strategy: You are a "doer" who thinks like an owner. You can design a 12-month roadmap but are equally happy getting your hands dirty in a database on a Friday afternoon
• Experience: You’ve likely spent 5+ years in RevOps, SalesOps, or a Technical Finance role within a B2B SaaS environment

How We’ll Know You’re The One
In your first 90 days, you’ll have mapped our current Odoo contract structure, identified three high-value expansion cohorts, and designed an automated communication-to-renewal workflow that requires zero manual intervention from the Sales team.

Why us?This is a high-leverage position. You won’t be a cog in a machine; you will be the one building the machine. If you love the challenge of turning "messy" legacy data into a streamlined, revenue-generating engine, this is your playground.
• The chance to make a decisive impact and shape the future of a dynamic, fast growing tech company while growing with your tasks and responsibilities
• Flexible and family-friendly working conditions in a stable environment
• With the wide range of sports and wellness offers from Wellpass, you can choose from over 9.000 sports and wellness offers
• A agile team that embodies autonomy and fast decision making within flat hierarchies
• A unique corporate culture where we emphasize equity, diversity and inclusion
• A wide range of education and training opportunities
• Fully remote work or high flexibility between mobile work and an office in one of the most beautiful, central district of Munich
• An attractive salary
• Regular onsite events of all sorts (Company Outings, Team events, Checkmk Conference, Conference After Party, and more) in a familiar atmosphere

Interested? Then contact us now! You can get insights about working@checkmk at: www.kununu.com/de/checkmk

About usWe are the creators of Checkmk, a leading hybrid IT monitoring software for both cloud-native and traditional infrastructures and applications. Checkmk is available as an open-source and commercial edition. We are a strong team of software developers and DevOps, open-source enthusiasts and nerds who are passionate about helping small and large companies run their complex IT infrastructures reliably. Over the last years we have grown from 20 to over 250 employees to support our customer growth in Europe, the US and beyond. Our colleagues currently work from our Munich HQ as well as across Germany, Italy, Austria, France, Spain, Poland, USA, Singapore and Malaysia.

We are a dynamic, fast growing and easy-going company where positive collaboration is very important. We are more than just colleagues; we have a strong team and a great customer community. For us, high autonomy and flat hierarchies are not just words on paper, but everyday life. With us you don’t work as one of hundreds or on purely theoretical questions but have an immediate positive influence.

With our product, we make the lives of thousands of administrators easier and help them in coping with the increasing complexity of IT. Our customers love our product and your work helps to keep it that way!