It’s been a chaotic yet defining year for Jaspar Carmichael-Jack, the 23-year-old founder and CEO of Artisan. One of the most headline-grabbing players in the fast-evolving AI sales agent space. Artisan just closed a $25 million Series A round led by Glade Brook Capital, with follow-on participation from Y Combinator, Day One Ventures, HubSpot Ventures, and several others. Solidifying the startup’s momentum after raising $12 million last September.
Born out of the Winter 2024 Y Combinator batch, Artisan quickly made a name for itself with its audacious marketing. Including its now-infamous “Stop Hiring Humans” billboard campaign in San Francisco. The move stirred viral attention and backlash, enough that Carmichael-Jack briefly “resigned” as CEO in an April Fool’s prank, declaring he’d be replaced by an “AI CEO.”
But behind the viral stunts lies a company navigating the real pains of early-stage growth in a volatile new category: AI sales development representatives (AI SDRs). Artisan is part of a growing wave of startups promising to automate outbound sales. Yet, as Carmichael-Jack admits, the path hasn’t been smooth.
Early versions of Artisan’s flagship agent, Ava, suffered from high customer churn and “cringeworthy” email hallucinations. “I just cringe in pain” reading the sales pitches Ava wrote during its YC days, Carmichael-Jack said. But through deeper collaboration with model provider Anthropic and the use of tighter, more rigid prompts. Artisan now claims that Ava “hallucinates maybe one in 10,000 emails.” That refinement helped the startup reach 250 paying customers and hit $5 million in annual recurring revenue (ARR).
Along the way, Artisan brought on a new CTO, Ming Li, whose résumé includes stops at Deel, Rippling, TikTok, and Google. A sign the company is investing in technical leadership to match its fast growth.
Artisan is also preparing to launch two additional AI agents by the end of 2025. Aaron, designed to handle inbound messages, and Aria, a smart meeting assistant. The goal is to build a broader AI sales stack that can operate across the entire funnel — not just cold outreach.
Yet, Carmichael-Jack has also learned that AI SDR isn’t for everyone. The company now refuses to work with certain industries, including offshore dev agencies, where automated outreach often underperforms. “We’ve historically sold to a lot of the wrong customers,” he said. Artisan now qualifies clients more rigorously and allows them to exit early through built-in break clauses.
Part of Artisan’s pivot is philosophical. “If we don’t get [customers] value, then we shouldn’t be charging them money,” says Carmichael-Jack. That belief led Artisan to pilot a “success-based pricing” model via Paid.ai, a new billing platform from Outreach co-founder Manny Medina, which allows customers to pay per lead rather than signing long-term SaaS contracts.
Artisan is also working to improve targeting. Much like its peers in the AI SDR space, the company is incorporating data from funding announcements, news articles, and social media signals to help determine who to contact — aiming to deliver fewer but more meaningful conversations. The startup’s proprietary database of brick-and-mortar businesses is another differentiator it claims gives it an edge in market segmentation.
Despite some hard-learned lessons, Carmichael-Jack remains bullish. “Human labor becomes more valuable when you have the AI content,” he says. Artisan isn’t replacing people — it’s redefining how they work.
