Senior Director of Sales

Summary

Join Aiwyn as a Senior Director of Sales and become the CRO's right hand in leading and scaling the Account Executive organization. This pivotal leadership role involves building a high-performance team, fostering a thriving sales culture, and driving sustainable revenue growth. You will own all aspects of sales execution and strategy, combining sales best practices with creative thinking to shape commercial strategy. The role requires strategic leadership, hands-on coaching, and building a culture of autonomy, mastery, and purpose. Success in this position will ensure Aiwyn's continued top-quartile YoY growth. Aiwyn offers competitive compensation and a range of benefits, including a remote work culture, flexible PTO, and comprehensive health benefits.

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
• 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

Responsibilities

• Recruit, onboard, and develop a team of elite sellers
• Set the bar at remarkable for your team and foster a culture that multiplies their individual super powers
• Build out additional management layers over time, supporting the professional growth and career paths of all team members
• Partner with the CRO to define, refine, and execute our go-to-market strategy
• Drive predictable, scalable revenue growth by running world class processes around territory, pipeline, and forecast management
• Collaborate cross-functionally with Marketing, Post-Sales, Product, and Revenue Operations to ensure we’re running a best in class revenue motion end to end
• Bring a GM mindset—owning both top-line growth and cost-effectiveness to deliver maximum ROI
• Partner with your team to develop innovative sales plays, commercial structures, and value engineering tailored to our growing solution offering
• Experiment with new approaches (leveraging AI, new tech, or novel techniques) to push the boundaries of modern selling
• Regularly engage with C-level and VP-level executives at prospect and customer organizations, becoming a student of their businesses, and building trust/credibility alongside your team
• Promote a sales culture centered on autonomy, mastery, and purpose— inspiring the team through empowerment and the desire/ability to have massive impact on Aiwyn, our team, & our customers
• Partner with the Revenue Excellence team to build training programs, playbooks, and ongoing enablement efforts that derisk the GTM strategy and continuously elevate how our team executes
• Track, analyze, and report on sales performance metrics (e.g., pipeline coverage, win rates, cycle time, territory penetration, etc), leveraging modern GTM tools like Salesforce, Clari, and conversational intelligence
• Be a student of the “science of sales”. Use data to identify trends, opportunities, and gaps, then recommend approaches to iterate & improve

Preferred Qualifications

• 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

Benefits

• Adventure travel stipend - you receive a $1,000 travel reimbursement on your work anniversary each year
• 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