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.
If you are an AE that is passionate about the art and science of sales, love living on your “growth edge”, are looking to be one of the very best in the world at your craft, and thrive on building things that will stand the test of time, we want to meet you.
To learn more, visit our website
About the Role
We’re building a team of elite account executives to help the most innovative accounting firms on the planet accelerate their time to revenue and provide their clients/partners with world class customer experiences.
We are seeking proven high performers to over-achieve sales & pipeline objectives while establishing long-term relationships within assigned net new logo named accounts.
In partnership with a dedicated SDR and Solution Engineer, and reporting to the Senior Director of Sales, you’ll own the entire sales cycle from the first conversation and be part of a seamless post-sales transition. You’ll focus on creative prospecting, strategic account prioritization, multi-threading, whitespace identification, pipeline generation, and executing a modern and thoughtful sales process.
Success in this role requires the ability to flex between faster-moving cycles and more complex, consultative sales motions. You’ll know when to move quickly and when to step back and guide a buyer through longer-term decision-making. The best AEs at Aiwyn understand how to meet buyers where they are while staying aligned to shared outcomes.
This role can be worked from any location in the US.
What You'll Impact:
- 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
What You'll Bring From Past Experience:
- 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
Bonus: Experience selling into top 500 accounting firms or professional services
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.
- 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
Other benefits include:
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
Top Skills
What We Do
Aiwyn helps leading accounting firms automate and optimize critical revenue processes by unlocking client data from existing practice management and CRM systems with our Practice Automation platform.
With Aiwyn's Practice Automation platform, high-value firm executives, partners, and staff are liberated to deliver more value to clients and work at the highest end of their professional expertise.
Benefits of Practice Automation to accounting firms include:
- save time, bill faster
- eliminate tedious back office tasks
- reduce days-in-WIP and days-in-AR,
- speed up client payments
- smooth out cash flow
- protect financial health with predictive insights and controls
- offer a best-in-class experience to both employees and clients
