In Sunset Harbor, a 10 person fintech team works beside a 1,000 pound bank vault its CEO says he bought on Facebook Marketplace for a few hundred dollars. A short drive west, in Wynwood, a newly formed AI services division is trying to double its headcount. Both moves surfaced on the same day, Oct. 22, 2026, and both point at the same customer: the South Florida business that is too small for a consulting firm and too busy to build its own AI team.
The first is BOB, which says on its official site that it is "your AI agent for business finances," and which announced a $5.5 million seed round. The second is Terminal, which said in a Business Wire release that it has acquired Miami based Stationed AI to launch a new division called Terminal AI. One deal is about software that acts like a finance employee. The other is about people, engineers who embed inside a company and build AI into its daily work.
For owners of roofing companies, restaurants, agencies, clinics and service shops across Miami-Dade, Broward and Palm Beach, the pair offers a useful look at where local AI money is going and what it may soon be pitching to them.
BOB's $5.5 Million Seed Round
According to Refresh Miami, BOB raised $5.5 million in seed funding in a round led by Mischief, the venture firm founded by Plaid co-founder Zach Perret. Other participants named in the report include investor Peter Thiel, entrepreneur and investor Codie Sanchez, Zynga founder Mark Pincus and Karman Ventures, along with additional investors and operators. FinSMEs reported the same lead investor, the same participants and the same $5.5 million total.
Both reports say the money will go toward expanding product capabilities, scaling customer onboarding and growing the team in Miami. Refresh Miami reported that BOB launched a private beta the month before the announcement and that 500 businesses had already signed up, with the product currently free for those users.
CEO and co-founder Adam Wininger described the goal in plain terms to Refresh Miami. "We're trying to build the most useful banking product in the world, and we think that'll feel much more like an employee in your company rather than a dashboard to log into," he said. "BOB is really an employee that's joining your company that happens to offer banking services."
Dustin Moring, a general partner at Mischief, framed the investment around a shift in what AI does with money. "BOB is attacking an immense market at the exact moment AI is moving from advising on transactions to executing them," he said, according to the report.
What BOB Says It Does
FinSMEs describes BOB as an AI finance employee and banking platform that handles bookkeeping, invoicing, payments, deposit accounts and cash flow management for small business owners. Instead of a new dashboard, the company says owners interact through channels they already use. Refresh Miami lists WhatsApp, text messaging, Slack, Microsoft Teams, email and the company's own app.
The company site makes the same pitch in shorter form. "Text him. Slack him. Email him," it says, adding that BOB "plugs into the accounting, invoicing and estimating tools you already run your business on." The site also includes a line every owner should read closely: "You have final say on any communications, money movement, or reconciliations."
The fine print matters too. BOB's site states that it is a financial technology company and is not a bank, and that bank deposit services are provided by Erebor Bank NA, Member FDIC. The site also notes that crypto and blockchain settlement rails, where available, are not deposits and are not FDIC insured.
Built for Main Street Service Firms
Refresh Miami reported that BOB is focused on Main Street service businesses such as roofing contractors, restaurants and local services firms, a group the report describes as traditionally underserved by mainstream software.
Wininger told the outlet he has run small businesses himself, including a hotel company. "I know that these finances are a mess for so many businesses," he said. "And a lot of these business owners don't know how to get all this stuff set up with AI, it's scary. So we're really trying to help them run their business better, have better visibility into what's going on, and just give them a lot of their time back."
The team is local by design. Refresh Miami reported that BOB has 10 people, all in the Miami area, which Wininger described as a requirement, and that the company is hiring engineers. Its office in Sunset Harbor is set up like a 1940s Swiss bank, vault included.
Terminal Buys Stationed and Launches Terminal AI
The second deal came from a company better known for hiring than for building. Terminal describes itself as a talent platform for hiring AI fluent software engineers in more than 180 countries. Its release says that for nearly a decade it has helped companies including Hims and Hers, Calendly and GoPro source, vet and hire thousands of engineers.
With the purchase of Stationed AI, Terminal launched Terminal AI, a services division aimed at the mid-market. Financial terms were not disclosed in the release. Refresh Miami, in a report republished by Miami Business Magazine, said Terminal was co-founded by Palantir and 8VC co-founder Joe Lonsdale, Atomic founder Jack Abraham and CEO Dylan Serota, and that Terminal was founded in 2017.
Stationed was founded by Ja'dan Johnson, who also founded Miami Hack Week. The release says Johnson will lead Terminal AI as general manager. "Our customers know their business, and we know AI," Johnson said in the release. "The hard part is putting AI into practice, connecting to systems, data, and workflows that actually run a business."
Serota made the case for smaller companies directly. "The AI industry is pouring billions into transforming the world's largest enterprises, but millions of businesses are being left behind," he said in the release. "They don't need a consulting firm telling them AI is important. They need engineers who can show up, understand their challenges, and build something that works."
The Forward Deployed Engineer Model
The phrase at the center of the Terminal deal is the forward deployed engineer. In the release's description, these engineers embed with a company, learn how the work gets done and build custom AI agents around high value workflows "in weeks, not months."
Terminal AI organizes each engagement around three services, according to the release:
- Deploy: forward deployed engineers embed with a company and build custom AI agents around high value workflows.
- Hire: companies can scale an engagement with embedded engineers or hire dedicated talent through Terminal's global platform.
- Train: practical training and role specific playbooks aim to build AI fluency so teams can own and extend what gets built.
The release says each engagement starts by "attacking one painful workflow," then expands to the next opportunity. Serota offered a concrete size target. "A 200 person company can now bring in engineers to build AI directly into its operations, hire the talent to scale it, and equip its own teams to take it further," he said.
Hiring in Wynwood
For the local job market, the Refresh Miami report carries the most practical detail. Terminal AI has approximately 10 employees with another 10 positions open, and Johnson said the company is actively recruiting engineers in Miami to work from its Wynwood office. "We're going to keep hiring," he said.
The report traces how the deal came together. Johnson began organizing workshops to introduce business leaders to AI tools while building Stationed, which had already deployed AI agents for companies across several industries. After roughly a month of conversations with Terminal's leadership, the two companies decided to join forces. Johnson, who is originally from Jamaica, told Refresh Miami, "I'm excited to keep doing this work, and being able to do it at scale."
Between BOB and Terminal AI, roughly 20 people are already at work on these two efforts in Miami, with more roles open at both companies, based on the figures each reported.
What the Two Deals Have in Common
The two companies take different routes to the same customer. BOB delivers AI as a product, a finance agent that lives in a text thread. Terminal AI delivers it as a service, engineers who sit with an operations team and build custom tools. Both say the businesses they serve lack enterprise budgets and in house AI staff.
Both also lean on Miami as a base. Wininger told Refresh Miami that "Miami's the best city to build a company in," citing salaries, talent retention and the number of investors relocating to the area. Johnson described the Wynwood team as a way to keep building close to the companies that use the technology.
For owners, the takeaway is not that one approach wins. It is that local vendors are now offering AI at price points and team sizes aimed at small and mid sized firms, and owners will increasingly be asked to choose between software that acts and people who build.
A Checklist Before AI Touches Your Books
Any tool that can send invoices or move money deserves the same scrutiny an owner would give a new bookkeeper. A short list of questions helps, whatever vendor is on the other side of the table:
- Approval controls: confirm who must approve payments, messages and reconciliations, and whether that rule can be changed without the owner's sign off. BOB's site says the owner has final say on each of these.
- Where deposits live: ask which bank holds funds and whether deposits are FDIC insured. BOB names Erebor Bank NA, Member FDIC, and states it is not a bank itself.
- Read only first: start by connecting accounting tools in a view mode where possible, then expand permissions after a few weeks of clean results.
- Audit trail: make sure every action shows what was done, when and on whose approval. BOB's site says it "shows you what he did."
- Exit plan: ask how to export records and close the account if the fit is wrong.
- Accountant review: keep a CPA or bookkeeper in the loop at month end and at tax time.
How to Scope a First AI Project
For owners weighing a services model like Terminal AI's, the release offers a useful rule of thumb: start with one painful workflow. A first project goes better when the owner can name it in a sentence, such as quoting jobs from site photos, chasing late invoices, sorting inbound leads or reconciling supplier statements.
Before any vendor meeting, write down how many hours that task takes each week, who does it now, which systems it touches and what a good result looks like in 30 days. Ask any vendor who owns the code and the data when the engagement ends, how staff will be trained to maintain it, and what the total cost is for the first workflow before any expansion.
Owners who want to build skills before buying can find free and low cost AI training across the region, and a list of tools local firms already use is a good benchmark for what a custom build should beat.
Sources
Primary and reporting sources: BOB official site; Refresh Miami on the BOB seed round; FinSMEs on the BOB seed round; Terminal release on Business Wire; Refresh Miami report via Miami Business Magazine on Terminal and Stationed.
Related
More for owners sizing up AI: AI tools South Florida businesses are actually using right now and a free Claude AI workshop in Coconut Grove on Nov. 10.
Key Facts
How much did Miami startup BOB raise?
BOB raised $5.5 million in seed funding, announced Oct. 22, 2026. Mischief, the venture firm founded by Plaid co-founder Zach Perret, led the round, according to Refresh Miami and FinSMEs. Peter Thiel, Codie Sanchez, Mark Pincus and Karman Ventures also took part. The money will expand the product, scale onboarding and grow the Miami team.
What does BOB do for small businesses?
BOB describes itself as an AI agent for business finances. Reports say it handles bookkeeping, invoicing, payments and cash flow visibility through WhatsApp, text, Slack, Teams, email and its own app. Its site says owners keep final say on communications, money movement and reconciliations. BOB is not a bank; Erebor Bank NA, Member FDIC, holds deposits.
What did Terminal buy in Miami?
Terminal, a talent platform for hiring AI fluent engineers in more than 180 countries, acquired Miami based Stationed AI and launched a division called Terminal AI. Stationed founder Ja'dan Johnson, who also founded Miami Hack Week, leads the division as general manager. Financial terms were not disclosed in the Oct. 22, 2026 release from Terminal.
Is Terminal AI hiring in Wynwood?
Yes. Refresh Miami reported that Terminal AI has about 10 employees and another 10 open positions, and that it is actively recruiting engineers in Miami to work from its Wynwood office. Johnson told the outlet the company will keep hiring. Candidates should check Terminal's official channels for current openings and role requirements.
What is a forward deployed engineer?
In Terminal's description, a forward deployed engineer embeds inside a client company, learns how the work gets done and builds custom AI agents, automations and integrations around high value workflows. Terminal says engagements start with one painful workflow and aim to deliver working results in weeks, then expand through hiring and staff training.
