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Chief of Staff

€50K–€90K Full-time Berlin Apply by 9 Nov Apply for this role

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!

Apply

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