Head of Sales

Caseware is one of Canada's original Fintech companies, having led the global audit and accounting software industry for over 30 years, with more than 500,000 users across 130 countries and available in 16 different languages. While you might not have heard of us (yet) over 36,000 accounting and audit professionals list Caseware as a skill on their LinkedIn profiles!

As Regional Sales Leader for Germany at Caseware, you lead and develop a team of sales representatives while acting as the operational backbone of the region. You bring firm, timely decision-making, a supportive and solution-oriented coaching style, and the discipline to build a sustainable, long-term sales organization for Germany.

Acting as an operational excellence driver: proactively identifying and resolving systemic bottlenecks in the regional sales operation, with particular focus on pricing and the operational processes. Help deliver annual and quarterly revenue targets for the region by building and executing a regional sales plan with clear priorities and measurable outcomes. Drive consistent pipeline creation through outbound activity and targeted prospecting, and improve win rates through strong qualification and structured deal management. Identify and prioritize high-potential segments across firms, corporates, and the public sector, and support new-business development to expand Caseware's reach in the region. Maintain accurate forecasts and transparent pipeline visibility, and support the team on complex opportunities with preparation, commercial clarity, and decision-maker alignment. Set clear expectations for day-to-day team performance, activity standards, and territory focus, and strengthen the team through ongoing coaching and consistent feedback. Run reliable operating rhythms — pipeline reviews, deal inspections, and quarterly planning — and flag performance gaps and blockers early so the team can close business efficiently. Advocate directly for the team and region, while fully committing to agreed direction once decisions are made. Maintain disciplined use of Salesforce and drive data accuracy, and help shorten sales cycles by refining qualification and removing unnecessary steps. Ensure a smooth handover to Customer Success / Consulting so the team delivers a seamless customer experience and strong retention and expansion.

Experience leading or coaching a sales team, ideally within enterprise or complex B2B software / SaaS sales. A hands-on, operational mindset, with a track record of tightening up process, pricing, or deal execution. Solid understanding of the Software as a Service (SaaS) business model and ARR-driven sales organizations. Firm, timely decision-making and a results orientation, with the ability to move quickly from plan to execution. A direct, constructive, and solution-oriented communication style. Demonstrated ability to coach, develop, and retain sales talent. Comfort working with pipeline management, forecasting, and CRM discipline (Salesforce or similar). Strong cross-functional collaboration skills, working effectively with Marketing, Product, RevOps and Customer Success. A structured, dependable, and detail-oriented approach to sales operations and long-term customer partnerships. Knowledge of audit, finance, or accounting is a plus. Fluent German and strong English communication skills, both written and spoken.