Technical Operations Engineer

Skydive vs Town in 2026. t+t this+that team · August 31, 2026 Both products want to be the AI that does your work rather than drafting it for you. Town gives you one assistant that learns how you personally work. Skydive gives you a roster of agents, each with a name, a role, and a computer of its own. That single decision runs through everything else: how memory works, what you pay, and who on your team gets value. Key takeaways. * Town is one assistant per person. Skydive is many agents per company. Town's memory profile is built around an individual. Skydive's memory belongs to each agent and its templates are per role. * Skydive agents get their own computers. A browser, a file system, and a terminal each, so an agent can log into a tool with no API. Town works through its integrations. * Town raised far more. A $55M Series A led by a16z and Forerunner in June 2026, against an $11M Series A for Anything, which builds Skydive. * Skydive automates on a clock. Town's automation is the more reactive of the two. Skydive's Routines run on a schedule by design. Town has routines with triggers, three autonomy modes, and proactive monitoring of your connected accounts. What Town is. Town launched from founders with a strong pedigree: Jean-Denis Greze, formerly CTO at Plaid, and Tony Vincent, formerly of Google applied AI, both ex-Dropbox. The positioning is "the AI assistant that learns how you work," and the product is shaped around one person. You get a dedicated @town.com address, so you can forward or cc work to your assistant. Town also watches your connected accounts and surfaces things proactively rather than waiting to be asked. It covers email, calendar, Slack, WhatsApp, Telegram, documents, iOS, desktop, and web, with more than thirty third-party integrations across CRM and project management. The memory profile is the center of it. Town accumulates your voice, your preferences, and your patterns, and gets better at sounding like you and anticipating what you need. Three autonomy modes let you move from read-only to approval-required to autonomous as trust builds. Town raised a $55M Series A led by a16z and Forerunner in June 2026, with First Round, Alt Capital, and Conviction also participating. What Skydive is. Skydive launched publicly on August 20, 2026, built by Anything, an AI app builder with over a million users founded by former Google product leaders Dhruv Amin and Marcus Lowe. Rather than one assistant, you build a roster. Describe a role and Skydive assembles an agent for it, with a name and persistent memory. Templates ship for Chief of Staff, Engineer, Customer Support Manager, and Project Manager. The distinctive part is that each agent gets its own cloud computer, with a browser, a file system, and a terminal. That lets an agent log into a tool that never published an API and click through it the way a person would. You reach the same agent from web, Slack, email, iMessage, desktop, CLI, or API, and it keeps one memory across all of them. Each agent can also have an email address on your domain, so anyone can email it directly. Skydive supports more than 170 models and lists well over a hundred integrations. Where the two actually differ. Memory scope. Town's memory is personal. It learns one individual deeply, which is what makes it good at drafting in your voice and anticipating your week. Skydive's memory is per agent, so your support agent accumulates support knowledge. Neither pools knowledge across a whole team by default, but they fail to in different directions: Town's knowledge is locked to a person, Skydive's to a role. Reach into tools. Skydive's browser-equipped agents can reach systems no connector covers. Town works through its integration list, which is well chosen for CRM and project management but bounded by what's on it. Who the buyer is. Town sells to an individual executive or knowledge worker who wants a chief of staff. Skydive sells to a company that wants to add capacity without adding headcount. That shows up in the pricing. Pricing model. Skydive charges $20 a month for Starter, covering up to five users, and $200 for Team. Agents are unlimited on both, and usage is billed on top at a stated 0% markup on model cost. The plan fee is a floor, and what you spend depends on how much your agents run. Town prices per user in the way you'd expect of a personal assistant. Maturity. Town has been in market longer, has a larger team, and raised five times as much. Skydive is days old with thin third-party coverage. Town is the safer operational bet today; Skydive is the more novel architecture. How each one decides to act. Skydive is explicit about where it sits. Their Routines page is titled "Agents That Run on a Schedule," and their FAQ describes a Routine as work an agent runs on its own schedule, with examples like every weekday at 9am and the first of each month. Their own worked example is a weekday inbox summary, which reads the inbox on a clock. There's no event trigger on the page. Town is further toward reactive. Its routines carry triggers, and it monitors your connected accounts to surface things before you ask. If you want an assistant that notices, Town is the closer fit of these two. The distinction decides which problems each one solves. A scheduled run is exactly right for a morning briefing or a monthly report. For a request that arrives at 2pm and needs answering, a schedule means it waits. Which one should you pick. Pick Town if you're one person who wants an assistant that knows you: your voice, your calendar, your priorities. The memory profile is the product, and it's good at what it's for. The funding and team size also mean it's likely to keep shipping. Pick Skydive if you're a team that wants roles filled rather than one person supported, especially if your work runs through tools with no decent API. Unlimited agents make it cheap to give one person a lot of coverage, as long as you can live with a usage-based bill and with Starter's five-user cap. Neither is the answer if the work getting missed belongs to a team rather than to one person. Town's proactive monitoring covers its single user well, and Skydive covers what its schedule reaches plus whatever someone sends an agent directly, but neither pools arriving work across everyone. Where Thisandthat fit. this+that is built for the team rather than the individual, and that changes what the product is for. Thisandthat read Gmail, Outlook, Slack, Microsoft Teams, Google Chat, and WhatsApp Business as one stream of incoming work, and a message landing is what sets the work off. The requests, commitments, and follow-ups inside those messages become tasks in DoBox, assignable and visible to the whole team rather than sitting in one person's private thread with an assistant. Workflows act on them as they arrive. And the knowledge layer is shared. Its brain is one layer that every teammate and every workflow reads and writes, filling itself from the conversations your team is already having. That's the piece neither a personal memory profile nor a per-agent memory gives you. Thisandthat hold SOC 2 Type I as of July 31, 2026, with Type II underway. Frequently asked questions. Is Skydive the same company as Anything? Skydive is a product built by Anything, so the funding to compare is Anything's: an $11M Series A led by Footwork. Does Town or Skydive cost more? They price on different axes, so it depends on shape rather than size. Skydive's Starter is $20 a month for up to five users with unlimited agents, plus usage billed on top. Town prices per user. The structural difference is that Skydive meters agents and usage rather than heads, but Starter still caps you at five people. Can either one read my inbox without me forwarding things? Yes, both connect to your email. Skydive's integrations let an agent read and send from Gmail, and Town monitors your connected accounts proactively. They differ on when they act: Skydive's Routines run on a schedule, while Town's proactive monitoring and triggered routines are closer to reacting as things land. Which has better memory? They're built for different scopes. Town's memory profile goes deep on one individual. Skydive's memory belongs to each agent and improves from your corrections to that agent. If you want knowledge shared across a whole team, neither is designed for that. Which is more mature? Town, comfortably. It has been in market longer, raised $55M against Anything's $11M, and has a larger team. Skydive launched on August 20, 2026, and third-party operating experience is still thin.

Town, which is growing personalised AI assistants that connect with customers' e-mail and calendar, raised a $55M Series A led by a16z (Lily Mae Lazarus/Fortune). Lily Mae Lazarus / Fortune: Town, which is growing personalised AI assistants that connect with customers' e-mail and calendar, raised a $55M Series A led by a16z - Jean-Denis Gréze's AI assistant is a silver fox who wears somewhat satchel, and her title is Ivy. - Ivy is Gréze's Townie... Updated on June 03, 2026

Jean-Denis Grézé’s AI assistant is a silver fox who wears a little satchel, and her name is Ivy.  Ivy is Grézé’s Townie—the personalized AI assistant at the center of his startup, Town. His choice of mascot, an homage to his prematurely grey hair, says something about the product’s philosophy: this isn’t a chatbot. It’s yours. …