Everyone at Checkpoint has the option of a 4-day work week for 5-day pay. We value work-life balance and the promotion of your creative endeavours outside the office.
- Pay
- €50,000 to €90,000 a year, depending on billings and sales
- Job type
- Full-time
- Location
- Must be based in Berlin
- Apply by
- 9 November 2026
Also for every role: flexible working hours, home office, company-paid training and a mentoring program.
As Chief of Staff, you'll work closely with the founder and keep projects moving, both with our clients and inside Checkpoint GTM. We're a small, senior team building revenue systems for B2B SaaS companies, and strong project management is what turns that work into results.
The role is a hybrid. On the client side, you'll run projects end to end: scoping, timelines, budgets, stakeholder communication and making sure we deliver what we promised. Internally, you'll coordinate the founder's projects and priorities and keep our own planning and delivery organized.
Full-time and based in Berlin, working in person with the team and with clients on a regular basis.
What you'll do
- Support the delivery of all Checkpoint GTM services. Explore our service offerings
- Run client projects end to end: scoping, plans, timelines, budgets and status reporting
- Be the day-to-day contact for client stakeholders and keep communication clear and on time
- Coordinate our consultants and engineers across several projects at once
- Spot risks early, manage scope changes and keep projects on time and within budget
- Coordinate the founder's internal projects and keep priorities, owners and deadlines on track
- Prepare meetings, proposals and the numbers behind decisions
- Keep our project tooling, documentation and HubSpot setup in shape
- Improve how we plan and deliver projects as the team grows
What we're looking for
- Proven project management experience: you've run several projects at once and delivered on time and within budget
- Experience in a client-facing role at a consultancy, an agency or a B2B SaaS company
- Highly organized, with a structured way of planning, tracking and following up
- Clear, confident communication with clients and with the team
- Calm under pressure and good at prioritizing
- Comfortable with numbers: budgets, hours, forecasts and reporting
- Hands-on with tools: project management software, CRMs and automation
- Fluent in English; German preferred
- Based in Berlin
Bonus points if you've
- Earned a project management certification (PMP, PRINCE2, Scrum or similar)
- Worked on CRM, RevOps or GTM projects
- Used HubSpot, Salesforce or another CRM beyond the basics
- Built automations with n8n, Zapier, Make or AI tools
- Worked at a startup or in a small, fast-moving team
You'll love this role if you
- Like keeping many moving parts on track
- Enjoy working with clients as much as with your own team
- Get energy from turning chaos into a clear plan
- Care about both the big picture and the details
- Want to grow with a young company
What you'll get
- Ownership of client projects from week one
- Close work with the founder and the senior team
- Exposure to a wide range of B2B SaaS companies and GTM projects
- Room to shape how we plan and deliver as we grow
- Mentorship from operators with 80+ implementations behind them
- Regular Berlin team days for strategy and team time
You'll leave with deep experience running GTM and RevOps projects with clients, and a clear view of how a consultancy works from the inside. If that sounds like your kind of challenge, we'd love to hear from you!
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