Commercial Account Executive

Summary

Join Aiwyn, a fast-growing software company, as an Account Executive and help innovative accounting firms accelerate their revenue. You will manage the entire sales cycle, from initial contact to post-sales transition, focusing on new logo accounts. This role requires proven sales performance, strategic account management, and strong communication skills. You will work closely with SDRs and Solution Engineers to achieve sales targets and build long-term client relationships. The position offers remote work flexibility and a competitive compensation package, including benefits and perks. Aiwyn values trust, courage, impact, and relentlessness.

Requirements

• 2 to 3 years of SaaS field selling experience
• A buyer-first mindset and commitment to delivering a seamless, value-driven experience at every stage
• Experience working in a multi-product or platform environment where deals require strategic packaging and positioning
• A proven ability to lead sales cycles between $25K and $250K with multi-stakeholder buying groups
• Advanced prospecting skills, with a desire to keep improving as the AI toolset evolves
• An entrepreneurial approach to running your territory like a business
• Student of Business Strategy - the ability to identify quickly and mold your sales strategy around strategic business initiatives within your target accounts
• Dynamic Presentation Skills - Ability to engage & hold the attention of C-level executives for 30-90 minutes both virtually and in-person
• Clear, confident, and concise communication, particularly in written form
• Familiarity with AI tools that support outreach, messaging, and productivity
• A passion for growth and learning
• A combination of humility, confidence, and hunger to become world-class at your craft

Responsibilities

• Identify, open, and close new logo-named accounts across the top 500 accounting firms in North America
• Manage $25K to $250K deals from first call to close, rooted in deep understanding of each firm’s strategic goals and business context
• Build and share a clear point of view on each account’s key drivers, and use that lens to guide messaging, discovery, and deal strategy
• Deliver compelling product demos and executive presentations that speak directly to the buyer’s priorities and needs, working with personas including Firm Partners, COOs, and CIOs all the way to tactical Operations teams
• Partner with your SDR to develop thoughtful outbound plays (emails, campaigns, calls, videos, LinkedIn) and respond to inbound leads with urgency and intent
• Collaborate with Marketing on account-based campaigns and in-person or virtual events tailored to your territory
• Align closely with the SDR to build coordinated account strategies and prioritize high-potential firms
• Ensure seamless transitions by partnering with Implementation and Customer Success to drive a smooth handoff and successful onboarding
• Earn trust as a strategic advisor through genuine curiosity, clear communication, consistent follow-up, and demonstrated expertise
• Stay sharp on industry shifts, buyer pain points, and competitive trends so you can guide conversations with relevant insights

Preferred Qualifications

Experience selling into top 500 accounting firms or professional services

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