Head of Revenue

Join us in redefining organizational administrative burden

Webware is on a mission to reshape how complex organizations are managed and run. We are administration infrastructure for complex, often highly regulated organizations. Helping people dramatically reduce time for compliance, processes, document management and regulation. With our powerful SaaS platform, Webware automates workflows and is driving real business results. 

Founded 23 years ago, we are in organizational transformation from a locally focused company to international scaleup - making this the perfect time to join as our new Head of Revenue and Growth. 

This role is for a
hands-on commercial leader

who is equally comfortable driving day-to-day sales execution and setting the strategic direction. You'll lead from the front, coach by example, and scale a high-performing sales organization. You and your team will be striving towards a 30% ARR/Revenue growth target. 

What you will own:

• Sales Strategy & Execution:

Define and implement a clear go-to-market and sales strategy across our core markets (Europe) and new potential markets (Africa).
- Team Leadership & Coaching:

Build, lead, and continuously develop a team of key account managers, sales professionals and customer success managers.
- Operational Excellence:

Introduce scalable processes, forecasting, CRM (Pipedrive/Hubspot), peer learning, KPIs, and review rhythms.
- International Expansion:

Guide our entry into new markets, adapting our model to diverse customer profiles and cultures.
- Marketing Coordination:

Define and coordinate a Marketing strategy to support our Revenue growth target, for example through event marketing and product marketing efforts.

What we are looking for:

We believe great sales leaders share a set of foundational strengths. To succeed in this role, you must have:

• 5+ years of experience

in B2B SaaS/software sales.
- A
track record of setting up, coaching and scaling sales teams

in multi-market contexts (ideally including international, multi-lingual teams).
- Experience overseeing demand generation and aligning marketing efforts with sales pipeline targets.
- A balance of
strategic thinking and hands-on execution
- Experience with both
mid-market and enterprise sales

.
- Exceptional communication and coaching skills - you grow people through clarity, structure, and feedback.

The 5 core competencies we look for:

1. Sales Team Leadership

– You've built and led high-performing teams.
2. International GTM Experience –

You've successfully worked across borders and cultures.
3. Commercial Rigor

– You bring structure, forecasting discipline, and accountability.
4. Coaching & Development

– You invest in people and build learning organizations.
5. Energy & Drive

– You inspire action and move things forward.

How you work

We care as much about
how

you lead as
what

you've achieved. At your core:

• You lead with purpose and principles - balancing performance with people.
• You're committed to clarity and structure but remain adaptable.
• You're optimistic and ambitious.
• You know that great leadership is about listening, enabling, and growing others.

Why Webware?

• You will be part of the management team and shaping our commercial journey
• Trust and support to build something big across Europe and other markets
• A transparent and performance-driven culture in transformation

About us

We are the team of 25 professionals and we have from 2002 developing market-leading information and document management platform designed to help organizations with 100+ employees manage their information and document lifecycle, digital signatures, internal communication, and workflows - securely and all on one platform.

Our work culture is built on four key values: Collaboration, Getting Things Done, Growth Mindset, Accountability and Trustworthiness. We have an informal team atmosphere and organize various team events. Our offices are in Tallinn, Telliskivi area and Tartu, city center.

The interview process

We like to involve relevant colleagues in our hiring process to get input and feedback: 

• Online introduction to Webware with our CEO
• Interview with management team
• Case-based interview with management team
• Closing talk including compensation, starting date, and all other practical details