About Playbook

Playbook® is building the Operating Memory for regulated industries.

In life sciences and other highly regulated sectors, companies run on thousands of written procedures SOPs, work instructions, policies, manuals, and how-to guides. Employees are expected to find, understand, follow, and stay trained on the right procedure at the right moment. That system is breaking under the weight of information overload.

Playbook® turns procedural documents into structured, usable data making critical operational knowledge consumable by humans, software systems, and AI agents. This living layer of procedural knowledge is what we call Operating Memory.

We work with leading global life sciences companies and are building the foundational data model for procedural knowledge in regulated industries. We're an Series A, founder-led start-up with high ambition, high standards, and a strong bias toward execution.

The role

As our first Head of Enterprise Sales, you will own how Playbook wins enterprise customers and build the team that does it with you. You report directly to our CEO and sit at the leadership table.

This is a player-coach role. You will close our most strategic deals yourself while hiring and leading the first Enterprise AEs. You will shape our sales motion, pricing conversations and go-to-market in DACH, and your feedback from customers will directly shape the product.

What you'll do

• Own and close our most strategic enterprise deals end to end, from first conversation to signed contract

• Sell to Heads of Quality, Regulatory Affairs and Operations, and win over IT, procurement and the C-suite

• Hire, onboard and coach Playbook's first Enterprise Account Executives

• Set quotas, territories and a commission plan, and build a high-performance, low-ego sales culture

• Define our enterprise sales process and own pipeline, forecasting and reporting to the CEO and board

• Work with marketing and product on ICP, messaging and customer insight in DACH

• Run complex, multi-stakeholder deals with intense cycles and validated-system requirements

• Partner with the CEO on flagship deals, pricing and commercial terms

What you bring

• Several years in B2B SaaS sales, with at least 6+ years closing complex enterprise deals across global enterprise accounts.

• A consistent record of hitting quota and the numbers to show it

• Experience selling into regulated industries, ideally Life Sciences (pharma, medtech, biotech) or financial services

• Experience hiring, coaching or leading AEs, formally or as a lead

• Comfort with long, multi-stakeholder sales cycles involving quality, compliance, IT and procurement

• Full professional proficiency in English; German or other European language would be great plus

• A builder's mindset: happy to create the process, not just follow one

Nice to have

• Selling QMS, document management, GxP or compliance software (for example Veeva, MasterControl or similar)

• Experience in a startup, ideally as one of the early sales hires

• An existing network among quality and regulatory leaders in DACH

• Familiarity with AI or knowledge-management products

What we offer

• Competitive pay: 50/50 Split (OTE: €230–280k), with uncapped commission and accelerators above target

• A seat at the table: report to the CEO, shape strategy and help decide where Playbook goes next

• A team you build: hire your own Enterprise AEs and grow as we scale

• A product that matters: help pharma teams work safely and compliantly, with technology that is new to the market

• Flexibility: hybrid work from Munich or anywhere in Germany, with regular travel