Director of Sales

What You'll Impact:

• Sales Leadership & Team Development
• Recruit, onboard, and develop a team of elite sellers that want to be the very best at their craft in the world
• Set the bar at remarkable for your team and foster a culture that multiplies their individual super powers to get there
• Build out additional management layers over time, supporting the professional growth and career paths of all team members


Sales Strategy & Execution
• 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


Commercial Creativity & Critical Thinking
• 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


Executive-Level Engagement
• 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


Culture & Continuous Improvement
• 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


Metrics & Accountability
• 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

What You'll Bring From Past Experience:

• Sales Mastery
• 6+ years of B2B software sales experience with at least 3+ 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.


Talent Sourcing & Development
• 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


Analytical & Creative Mindset
• 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


Familiarity with Modern GTM Tech Stacks
• Hands-on experience with platforms such as Salesforce.com, Clari, Highspot, Gong, Outreach, or other leading GTM technologies 


Executive Presence
• Confident and credible in front of CXOs; adept at navigating complex organizations and high-level business discussions
• Exceptional executive level written & verbal communication


Key Personal Attributes
• 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 and Perks:

• 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.


Other benefits include:
• 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

Our Values:

• Trust - We champion transparency, welcome differing perspectives, uphold accountability, and trust that others have good intentions
• Courage - We have the courage to take calculated risks and embrace change, knowing what worked in the past won’t always work in the future
• Impact - Rooted in determination and innovation, we chase extraordinary outcomes and impactful results
• Relentlessness - We approach challenges with an unwavering resolve, never settling for mediocrity, and always striving to surpass expectations

Learn more about Aiwyn:

• About us
• Why Aiwyn
• YouTube page