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.

What you will be doing:

• 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.

What you’ll bring:

• 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.

What's in it for you: ▪️Innovation is at our core. We work with cutting-edge technology in accounting and financial reporting, constantly pushing the boundaries to create impactful software solutions. ▪️We are committed to a collaborative culture, where your ideas are valued, and knowledge sharing is encouraged within a supportive, inclusive team. ▪️Work-life balance is important to us. We offer flexible work options, remote opportunities, and generous time-off policies to ensure a healthy work-life balance. ▪️We offer competitive compensation, including a competitive salary and comprehensive benefits ▪️We are driven by impactful work. Your contributions directly affect how our clients manage financial processes and drive their success. ▪️Recognition and rewards matter to us. We celebrate hard work through recognition programs, performance bonuses, and opportunities for career growth. ▪️We embrace global opportunities. Work on international projects and collaborate with a diverse, global team. About Caseware: Caseware's cutting-edge software products are meticulously designed for accounting firms, corporations, and governments. Our teams are continually collaborating, innovating, and building upon our existing suite of products. With a customer-focused mindset, we are building technology that is shaping what the future of audits, financial reporting, and financial data analytics will look like. With a recent strategic investment from Hg Capital in 2020, Caseware is now in its next major growth phase as we double down on the people and products that have made Caseware so successful to date. One of Caseware's core values is Many Voices, One Team and with that in mind, we're dedicated to building teams as diverse as our customers in an equitable and inclusive way. We welcome and encourage candidates of all backgrounds to apply. Should you require accommodations or have any questions at any point during the application or interview process, please e-mail our People Operations team at talent@caseware.com. Background Check: Any candidates successful in obtaining an offer for a position will need to successfully complete a background check through Certn.co which typically includes an Identity Verification and Criminal Record Check. Executives and Senior Managers will undergo a Soft Credit Check as well. Candidates residing in the Netherlands and Germany are excluded from undergoing background checks via Certn.co Security and Fraud: Caseware takes the security of candidates seriously. All legitimate communication from us will come from email addresses ending in @caseware.com and our open positions are always listed on reputable job boards and on our website https://jobs.lever.co/caseware. We will NEVER ask for payment or financial information from you. If you receive an unsolicited job offer, proceed with extreme caution.