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
This role:
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.
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
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.
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
Aiwyn is an equal opportunity employer. All qualified applicants will receive consideration for employment without regard to age, ancestry, color, family or medical care leave, gender identity or expression, genetic information, marital status, medical condition, national origin, physical or mental disability, political affiliation, protected veteran status, race, religion, sex (including pregnancy), sexual orientation, or any other characteristic protected by applicable laws, regulations and ordinances.
Candidate information will be treated in accordance with our CCPA privacy notice which can be found here:
https://www.aiwyn.ai/ccpa
