Shai Stern
About Shai Stern
Shai Stern founded CheckAlt, a payment processing company based in Los Angeles. Public profiles describe it as providing item processing, lockbox and treasury management services to financial institutions and corporate clients. He has been CEO and Co-Chairman there since 2010, and Crunchbase lists his primary organization as CheckAlt.
Before CheckAlt he began his career at American Stock Transfer Company. In 2002 he co-founded Vintage Filings, an EDGAR filing and financial print firm that PR Newswire acquired in 2007. He also co-founded Vcorp Services and Vcheck Global, and Vcheck Global was later sold to affiliates of Sunstone Partners. According to a 2025 press release, he has also served tens of thousands of clients across financial, legal and professional-services sectors through these companies.
In December 2025 he announced Gotavi with co-founders Elishah Herman and Michelle Miklosey. Gotavi is a business orchestration platform for entrepreneurs starting and running companies. Crunchbase places him in Los Angeles. A 2025 Jewish Link profile says he moved back to the Monsey, New York area in recent years after nearly two decades in Los Angeles. Crunchbase and his LinkedIn mention Yeshiva University. In an April 2026 LinkedIn article he says he dropped out of Yeshiva University about 30 years ago.
Data providers disagree on how many investments he has made. Crunchbase counts 5 investments, 4 portfolio companies, 1 lead investment and 0 exits. PitchBook, CB Insights and Tracxn each list 3 investments and classify him as an individual angel investor.
The dated rounds in those databases are Biller Genie (seed, March 2021), Scrypt AI (seed, April 2021), Finexio (August 2021) and Lama AI (seed, October 2022). He led the Scrypt AI seed round. Crunchbase also lists him as Chairman of DoubleBeam and an advisor to LocaLyfe. DoubleBeam, which also appears as GoPago, was acquired by Verifone in February 2015 according to one profile aggregator.
He is also listed on boards or advisory roles at Street Invoice, Zipmark, Bankjoy, VStock Transfer and S2 Filings. These are board and operating roles, and the sources do not say whether each was an investment.
His best-documented AI involvement is Scrypt AI. CheckAlt launched Scrypt with Composable Analytics to add machine-learning document processing and payment data capture to its services. Scrypt AI closed its first funding round in April 2021, led by Stern, with participation from Cross River Bank and several fintech executives. Preqin describes the company as using machine learning for invoice coding, digital payments and account reconciliation. It lists him as Co-Chairman alongside CEO Andy Vidan.
He also appears as an investor in Lama AI, which Startup Nation Central describes as an AI-powered lending exchange for small businesses. Its seed round in October 2022 is listed at $9M. That figure is the size of the round, not his check. His LinkedIn post about Scrypt AI says he was focusing on fintech, including payments, banks, credit unions and invoice processing.
Public data points to early-stage B2B fintech. Angel databases list his markets as B2B, information services, information technology and payments. ConnectSafely lists Seed as his stage and the United States as his geography, and Tracxn shows US portfolio companies only. These are aggregator tags, not statements from Stern.
He has not published a check size or investment thesis that we could find. Founders should not assume a range from the round sizes above, because those are totals across all investors. His operating background is in payments, check processing, invoice processing and filings, so pitches in those areas fit best with his experience.
- Scrypt AI: machine learning for invoice coding, payments and reconciliation. He led the seed round in April 2021 and is Co-Chairman.
- Lama AI: AI-powered lending exchange for small businesses. Seed round in October 2022, listed as his latest investment on Crunchbase and PitchBook.
- Finexio: B2B payments company. Tracxn lists his participation in an $8M round in August 2021.
- Biller Genie: billing and payments software. Seed round in March 2021, listed at $3.5M in total.
- CheckAlt: payment processing company he founded in 2004 (per MarketScreener) and has led as CEO since 2010.
- Gotavi: business orchestration platform for founders, which he announced in December 2025 with two co-founders.
- crunchbase.com/person/shai-stern
- marketscreener.com/insider/SHAI-STERN-A0PLQP
- worth.com/person/shai-stern
- finance.yahoo.com/news/shai-stern-elishah-herman-michelle-130000845.ht
- jewishlink.news/how-shai-stern-is-redefining-the-pipes-of-business-wit
- vcnewsdaily.com/access/getarticle.php?aid=ttshsyymbj
- preqin.com/data/profile/asset/scrypt-ai-llc/432594
- composable.ai/checkalt-and-composable-analytics-launch-scrypt-ai-data-
Investing activity
Shai Stern has made 5 investments according to Crunchbase across 4 portfolio companies, and has led 1 round.
Deals
Frequently asked questions about Shai Stern
Is Shai Stern an angel investor in AI startups?
Yes. He led the April 2021 seed round of Scrypt AI, where he is Co-Chairman. Databases also list a seed investment in Lama AI in October 2022.
What stage does Shai Stern invest in?
Public data points to seed. His dated investments are seed rounds in Biller Genie, Scrypt AI and Lama AI, plus Finexio in August 2021. He has not published a stage preference.
What sectors does Shai Stern back?
Databases list payments, B2B, information services and information technology. His portfolio is mostly fintech, including invoice automation, billing, B2B payments and lending.
What is Shai Stern's check size?
No check size is public. The $9M figure for Lama AI and the other round sizes in databases are totals across investors, not his own investment.
What companies has Shai Stern founded?
He co-founded Vintage Filings, Vcorp Services and Vcheck Global, and he founded CheckAlt. In December 2025 he announced Gotavi with two co-founders.
Where is Shai Stern based?
Crunchbase lists Los Angeles, California. A 2025 Jewish Link profile says he moved back to the Monsey, New York area in recent years.
Is Shai Stern an angel investor?
Yes. Shai Stern invests personally as an angel and is Founder at CheckAlt. Crunchbase counts 5 investments.
How can founders reach Shai Stern?
Founders on Lounge can see Shai Stern's contact details in AI Investor Contacts (paid plans), check for a warm introduction through members who worked with them under Warm Paths, and add Shai Stern to their Investor Pipeline to track the conversation.