Aiwyn
Aiwyn sells accounting software that automates payments, practice management, client experience and tax workflows. It has raised $127M and serves over 175 accounting firms.
The growth story
Aiwyn grew from 30 to 168 employees between 2021 and 2026, raising $127M along the way, most recently a Series A in December 2024.
About
Aiwyn makes software for accounting firms to automate manual tasks and consolidate systems across payments, practice management, client experience and tax. Its platform aims to reduce complexity and improve service consistency.
The company raised $127M in a Series A round in December 2024, led by Bessemer Venture Partners and KKR. It employs 168 people, with engineering making up the largest function at 46 staff.
Founders and leadership
Engineering is the largest function with 46 staff, suggesting a product-focused organization. The company has a median tenure of 1 year, indicating rapid scaling or turnover.
The Aiwyn org chart
Justin Adams (Chief Executive Officer, Co-Founder, and Chairman of the Board of Directors) leads 60 mapped leaders with 6 direct reports. Click +N to expand a team; names link to the person’s public profile.
Departments, and which ones grew
Headcount by function: Engineering 55 (-2% YoY), Customer Success and Support 15 (+25% YoY), Sales 15 (+25% YoY), Operations 13 (+8% YoY), Business Development 12 (-14% YoY), Information Technology 12 (+20% YoY).
Talent flow
Aiwyn hires heavily from accounting software firms, with Column Tax, KIS Solutions and QuickFee as top sources. Alumni most often move to fintech companies like Ramp and Documo.
Most common previous employers of Aiwyn staff: Column Tax (7), KIS Solutions (5), QuickFee (4), Mango Practice Management (3), Waystar (3), Digitize.AI (3). Former Aiwyn employees most often moved to Ramp (3), Documo (2), HubSync (2), Keel (2), Raft (2), Edgefield (2).
Alumni worth knowing
The Aiwyn mafia
Nine alumni have founded companies, including Validation Cloud (28 staff), Horizon Roofing (21 staff) and Rewired Technologies (7 staff).
10Alex N., was Investor until 2022Matthew Hultquist, was Founding Investor until 2024Drew Detweiler, was Director of GTM Operations until 2024Chad Osgood, was Entrepreneur in Residence, GM of Aiwyn Connect until 2026Samantha Baker, was Senior Director, Head of Marketing until 2023Marion Newman, was Technology Consultant until 2025
Andy Schrader, was Head of Product Management, Tax Division until 2026
William LeFew, was VP of AI, Business Lead (GM) of Tax until 2026
Alexander Kenis, was Director of Solutions and Technical Services until 2026
Henrique Menegale, was Frontend Engineer until 2025Web traffic
Traffic mix: 76% direct, 12% search, 0% social, 0% paid.
What this company is made of
Most common skills at Aiwyn: Leadership (74), Microsoft Office (55), Microsoft Excel (50), Management (50), SQL (49), JavaScript (48), Customer Service (45), Java (44).
Where the team actually sits
Aiwyn people are concentrated in North Carolina, United States (15), California, United States (12), São Paulo, Brazil (9), Texas, United States (7). 3 offices on record.
Search footprint
Aiwyn attracts about 392 organic search visits a month, traffic worth roughly $5K a month if bought through ads. It gained 108 ranking keywords and lost 61 in the last period.
What employees say
- Compensation
- 3.50 / 5
- Career opportunities
- 2.60 / 5
- Senior management
- 2.50 / 5
- Work-life balance
- 2.90 / 5
Frequently asked
Aiwyn has 168 employees as of September 2026.
Aiwyn has raised $127M in total, most recently a Series A round in December 2024.
Aiwyn was founded in 2020 by Justin Adams, Tanner Fritz.
Justin Adams (Chief Executive Officer, Co-Founder, and Chairman of the Board of Directors) sits at the top of Aiwyn's reporting structure, with 6 direct reports.
The most common previous employers of current Aiwyn staff are Column Tax (7 people), KIS Solutions (5 people), QuickFee (4 people).
Former Aiwyn employees most often move to Ramp (3), Documo (2), HubSync (2).
At least 9 companies have a founder who previously worked at Aiwyn, including Validation Cloud, Horizon Roofing, Rewired Technologies.
Aiwyn attracts about 392 organic search visits a month, worth roughly $5K a month in equivalent ad spend.
The most common skills among Aiwyn staff are Leadership, Microsoft Office, Microsoft Excel, Management, SQL.
Aiwyn staff are concentrated in North Carolina, United States (15), California, United States (12), São Paulo, Brazil (9).
Aiwyn has about 55 people in Engineering, down 2% over the past year, as of September 2026.
Aiwyn has about 15 people in Customer Success and Support, up 25% over the past year, as of September 2026.
Computed from 142 current and 130 former Aiwyn profiles, as of September 2026. Source: Crustdata.
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