Senior Director of Sales

February 10

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Aiwyn

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Aiwyn is a company that specializes in practice management solutions for accounting firms. Its flagship product, PracticeOS, helps optimize firm operations by automating administrative tasks such as billing, collections, engagement letters, and revenue cycle management. Aiwyn aims to enhance client satisfaction and improve cash flow for accounting firms through integrated and streamlined processes. By partnering with top accounting alliances, Aiwyn offers a platform that unifies tech stacks and allows firms to integrate third-party solutions, minimizing administrative burdens and maximizing efficiency.

artificial intelligence • accounts receivable • accounting firms • billing • collections

11 - 50 employees

💸 Finance

💳 Fintech

☁️ SaaS

📋 Description

• Who is Aiwyn and what do we do? • Aiwyn is transforming the way accounting firms streamline the entire revenue management lifecycle. Backed by top-tier investors (Bessemer, KKR & Revolution), we’re one of the fastest-growing scale-up software companies globally—delivering innovative technology and consistently raising the bar with world-class people, processes, and products. • We’re seeking a Senior Director of Sales who will be the CRO’s right hand in leading and scaling our Account Executive (AE) organization. This is a pivotal leadership role responsible for building a high-performance team, creating a thriving sales culture, and driving sustained, efficient revenue growth. • If you are passionate about the art and science of selling, thrive on developing elite talent, and excel in partnering with executive stakeholders to solve complex challenges, we want to meet you. • To learn more, visit our website • As the Senior Director of Sales, you will own all aspects of sales execution and strategy for our growing team of Account Executives, eventually building out layers of management as we scale. You’ll combine a deep understanding of sales best practices with creative, critical thinking to shape commercial strategy and win the hearts & minds of C-level executives at our clients and prospects. • This role requires a balance of strategic leadership and hands-on coaching, alongside a commitment to building a culture of autonomy, mastery, and purpose. Your success will ensure Aiwyn continues to deliver top quartile YoY growth as we transform the way accounting firms manage their revenue lifecycle.

🎯 Requirements

• 8+ years of B2B software sales experience with at least 4+ years in a managerial/leadership capacity. • Expertise in both the art and science of selling • Proven track record of driving significant revenue growth and leading high-performing teams in a fast-paced, scale-up environment. • Preferred experience with ASPs at $30K-200K, and average cycle lengths of 30-250 days. • Vertical SaaS experience is a plus. Ideally with AE territories containing 20-75 accounts. • Experience hiring elite commercial/mid-market AEs and building/maintaining a strong bench of both internal and external talent • Demonstrated success in coaching, mentoring, and inspiring world class execution • Ability to rigorously apply data-driven insights to shape GTM strategy for the team • Comfort with developing new programs or approaches that challenge the status quo and spark ongoing improvement • Hands-on experience with platforms such as Salesforce.com, Clari, Highspot, Gong, Outreach, or other leading GTM technologies • Confident and credible in front of CXOs; adept at navigating complex organizations and high-level business discussions • Exceptional executive level written & verbal communication • Intellectual Horsepower: You quickly grasp complex concepts and distill them into practical insights • Empathy, Integrity & Positive Attitude that all rub off on those around you • Curiosity & Lifelong Learning: You actively seek knowledge, staying ahead of evolving industry (Accounting) and domain (SaaS Sales) trends • Collaboration & Follow-Through: You thrive in cross functional environments and have elite follow through • Entrepreneurial Agility & Grit: You embrace challenges, remain resilient under pressure, and adapt to rapidly changing environments

🏖️ Benefits

• The big-picture value proposition of this role is simple: join us, and you'll be paid competitively to have freedom in solving worthwhile, challenging problems alongside other A-players at a fast growing SaaS startup led by an experienced and successful co-founding team with industry experience. • Adventure travel stipend - you receive a $1,000 travel reimbursement on your work anniversary each year. We encourage our team to recharge and explore the world beyond their home office walls. • Remote, work-from-anywhere culture • Flexible PTO • World Class health benefits - we believe in fostering flourishing teams by providing benefits that go beyond the usual standards - Health, vision, dental, HSA/FSA, and mental health support. • Stock options - every Full Time Employee has ownership in Aiwyn's future and success. • 401(k) matching