The hardest part of planning a corporate offsite isn't the creative brief. It's the 50-page hotel proposal, the back-and-forth over room blocks, and the phone calls to a convention center in Berlin at 2 a.m. local time. Nowadays, a seed-stage startup from Y Combinator's Winter 2023 batch, is betting that an AI agent can handle that grunt work, from sourcing venues to negotiating contracts, in nearly two dozen languages [Y Combinator, retrieved 2024].
Founded by sisters Anna Sun and Amy Yan, the company has raised $2 million to build what it calls an enterprise-grade event management platform [TechCrunch, Dec 2024]. The core proposition is pragmatic: replace weeks of manual email chains and spreadsheet comparisons with software that can parse proposals, contact venues, and secure rates autonomously. For procurement teams drowning in unmanaged meeting spend, it's a pitch that lands on efficiency. The question is whether it can scale from a useful assistant to a trusted enterprise vendor.
The wedge is the RFP, not the RSVP
Nowadays's entry point is the request-for-proposal process, a traditionally manual slog for corporate event planners. The company claims its AI can source venues from a database of over 400,000 vetted properties within minutes, a task it says takes days manually [nowadays.ai, retrieved 2024]. Once proposals come in, the system analyzes them, comparing terms and costs across what it says are hundreds of data points in seconds,a job that allegedly consumes 10 or more hours of human review [nowadays.ai, retrieved 2024].
The more ambitious claim is the AI's ability to negotiate. The platform says it can contact venues by email and phone to gather availability and discuss terms, handling outreach and follow-ups in 22 languages [Y Combinator, retrieved 2024]. This isn't just a chatbot sending templated emails; it's positioning the software as a direct proxy for the human planner in early-stage vendor discussions. For global companies, the multilingual capability is a clear differentiator.
A sister act with a procurement mindset
The founding team brings a blend of technical rigor and operational experience. CEO Anna Sun is a MIT graduate who worked in product and software engineering roles at Datadog, DoorDash, and Amazon [nowadays.ai, retrieved 2024]. COO Amy Yan partnered with her sister to plan events for over 3,300 students during their time as university class presidents [nowadays.ai, retrieved 2024]. It's a background that suggests they understand both the code and the chaos of large-scale logistics.
Their early backing hints at investor confidence in that combination. The $2 million seed round included Hike Ventures, Decacorn VentureUs, Y Combinator, Underdog Labs, and Basis Set Ventures, among others [TechCrunch, Dec 2024]. It's a classic party round for a YC company, providing runway to prove the model without a single dominant lead investor setting the immediate agenda.
Early traction and the path to enterprise
The company reports it has facilitated over $4 million in client bookings since launch [Instagram, Dec 2024]. While the firm does not disclose revenue or customer count, that booking volume suggests meaningful early adoption, likely among tech-forward mid-market companies. The business model appears flexible, with options for a 5% fee on managed events or an annual subscription, plus a free basic tier for smaller searches [Instagram, Dec 2024] [nowadays.ai, retrieved 2024].
The team is small, with public records indicating between 5 and 12 employees, and they are actively hiring, including for a software engineer intern role for Spring 2026 [Exa.ai, retrieved 2024] [LinkedIn, retrieved 2024] [nowadays.ai, retrieved 2024]. The leadership table below outlines the known core team.
| Role | Name | Background |
|---|---|---|
| Co-Founder & CEO | Anna Sun | MIT; PM & SWE at Datadog, DoorDash, Amazon [nowadays.ai, retrieved 2024] |
| Co-Founder & COO | Amy Yan | Previously planned events for 3,300+ students as class president [nowadays.ai, retrieved 2024] |
| Chief of Staff | Christina Chen | Not specified in provided sources |
| Founding Engineer | Vin Bui | Not specified in provided sources |
| Founding Product Engineer | Emily Zhang | Not specified in provided sources |
Where the model meets friction
The risks for Nowadays are familiar for any SaaS play automating a high-touch service. First, the competitive set is not asleep. Cvent owns a massive footprint in enterprise event management, and specialists like BoomPop cater to the corporate retreat niche. Nowadays's answer is its AI-native, vertically integrated approach, arguing that legacy platforms are built for registration and logistics, not for intelligent sourcing and negotiation.
Second, the renewal motion is unproven. Saving a planner 10 hours on vendor sourcing is a compelling productivity gain, but enterprise contracts are won on reliability, security, and cost control at scale. The platform's ability to handle complex, multi-million dollar event contracts end-to-end,with the attendant liability,remains its most significant proof point to land. The company's IATA certification and WBENC certification as a Women's Business Enterprise are early credibility signals for larger procurement departments [nowadays.ai, retrieved 2024].
Third, the AI itself is a black box in a high-stakes process. A miscommunication in a negotiation or a misinterpreted contract clause could be costly. The company's traction suggests it is navigating this, but the long-term bet requires near-perfect reliability.
The next twelve months
The immediate roadmap likely involves converting early booking volume into recurring enterprise contracts, proving that its AI can manage not just sourcing but the full event lifecycle for a portfolio of corporate clients. Key milestones to watch will be a named enterprise customer announcement, a shift toward clearer SaaS pricing metrics beyond a percentage fee, and potentially a Series A round to scale the sales and engineering teams.
Nowadays's ideal customer profile is clear: a mid-to-large enterprise with a distributed team, frequent internal meetings and offsites, and a procurement department actively looking to consolidate and control decentralized event spend. It's the company that has outgrown ad-hoc planning but isn't yet ready for a monolithic, seven-figure enterprise events suite.
The realistic competitive set breaks into three tiers. At the high end, Cvent offers depth and scale but less automation in the sourcing phase. In the middle, platforms like BoomPop offer full-service planning but with a human-led, not AI-led, model. At the lower end, a patchwork of travel agencies and venue brokers offers personal service but lacks the software integration and data aggregation. Nowadays is betting it can own the middle ground,software-driven, but with enough automated service to handle the heavy lifting that pure self-serve tools can't.
Sources
- [TechCrunch, Dec 2024] Y Combinator alum Nowadays, founded by sisters, raises $2M to automate event planning | https://techcrunch.com/2024/12/06/y-combinator-alum-nowadays-founded-by-sisters-raises-2m-to-automate-event-planning/
- [Instagram, Dec 2024] Nowadays, a 2023-founded event-planning AI startup... | https://www.instagram.com/p/DDXYeKvxz6O/?hl=en
- [nowadays.ai, retrieved 2024] Nowadays - AI Event Planner for Corporate Teams | https://www.nowadays.ai/
- [Y Combinator, retrieved 2024] Nowadays - AI Event Planner for Corporate Teams | https://www.ycombinator.com/companies/nowadays
- [LinkedIn, retrieved 2024] Nowadays | LinkedIn | https://www.linkedin.com/company/nowadays-ai
- [Exa.ai, retrieved 2024] Company profile data | Not available
- [Crunchbase, retrieved 2024] Nowadays - Crunchbase Company Profile & Funding | https://www.crunchbase.com/organization/nowadays-ai