Our Anthropic bill is about to jump from $400K → $1.4M/yr. Not because usage exploded, but because we're about to cross 150 seats. Past 150 seats you're forced into Enterprise tier. Seats stop including any usage, every token bills at standard API rates. At our current run rate that's 3.5x overnight. Unfiltered thoughts on AI spend: 1. We should spend tokens to grow as aggressively as possible. But most people (me included) aren't conscious of what they're spending. 2. Visibility comes first. People see their personal number and they're shocked. I accidentally spent $4,000 in 3 days in Claude Code. 3. For engineering the spend is clearly worth it. Pay for the best model, it saves more than it costs. 4. For a lot of other roles it's questionable. Apps nobody uses, skills someone already built. No ROI. 5. Spend limits are coming. We already require approval for more tokens on our support team. The era of token-maxxing is coming to an end.

The role of a support engineer is evolving. It used to look like... → Long, manual issue investigations → Lots of back and forth with customers to get context → Ping an engineer for help with a ticket and wait Now teams can... → Have AI run initial investigations → Ask AI to gather account context → Search the codebase directly with Claude Code or Cursor The goals of support haven't changed (provide fast and high-quality help, make it easy for customers to reach you) but the tools are making it so much easier to achieve those outcomes now. Next week we'll show you how we've been using AI tools for support, product, and GTM. Robert and Nikolaj Pedersen from our support team will demo three AI workflows we actually use, including projects from our internal hackathon last month. Join us June 10 @ 10 AM PT. Link to register in the comments 👇️

Product / design / engineering orgs of the future are vase-shaped. Small product team Big design team Small engineering team We've hit this point with AI where it's a significant multiplier for product and engineering capacity, i.e.: → It's easy for a lean engineering team to build and ship high-quality product super quickly → It's easy for individual PMs to do research and write PRDs at larger scale For example, engineers can spin up a dozen agents and make more decisions much faster than before. On the other hand design has yet to really hit its Claude Code/Cursor/Codex moment. There are some AI tools that help with parts of the design process, but they just don't allow the same level of parallelization or quality right now. So while many companies are hiring leaner engineering and product teams than we've seen historically, I think over time design teams will become more proportionally staffed.

Now in Pylon... Custom priority icons 🏷️ You can now replace our default priority labels and match Pylon's tags to your internal ranking system. Enjoy!

Our support team just crossed 100K tickets. That's 17,355 across Jon Clark (leads the team and 1st support hire) and Matthew Nagy (2nd support hire). 32,000 product questions, 26,000 feature requests, and 23,000 bug reports (top 3 categories). 5,000 issues from our top 10 most active customers. ...all handled with a 93% CSAT. On top of this, our support team is heavily involved in building and testing new Pylon products. They're a huge part of the reason we can ship high quality features so quickly, and are always the first to pilot workflows we eventually productize and release to customers. Congratulations to our support team for handling 100,000 (by now already 100,200 ) issues. Thank you for keeping Pylon running 🚀

New workflow: Send and set status ⚡ If you ever want to manually override AI auto-statuses in Pylon, you can now respond to an issue and set its custom status in the same action. → Draft your customer reply → Use the "Send" dropdown to set issue status on send → Use keyboard shortcuts to do it even faster Make sure tickets land exactly where you want them.

Testing something big and we're very excited about the results so far 🤫

We got a new addition to the customer portal... 🍀 Feature requests 🍀 → Turn on portal visibility for FRs → Select what metadata customers can see → Choose how FR statuses appear to customers Now customers can stay updated on their feature requests, right alongside their open tickets and tasks.

Here's how our first ever AI support hackathon went 👇️ What we learned from the event... 1/ For a lot of people, networking and just getting to chat with other attendees was super valuable in itself 2/ Our current customers got a ton of value out of meeting their Pylon CSMs in person (even if it was just a 15-30 min conversation in the middle of the day) 3/ It was awesome to see folks get excited about beta products we announced, but many people wanted deeper dives on use cases and how to set things up We had a great time and got such good feedback that we're planning a similar series of customer-focused workshops for this summer. Some of what we'll add based on your input... → Dedicated sessions with your Pylon CSMs → Event tracks so attendees can go deep on specific Pylon products or workflows they want to learn about → Small group sessions to facilitate different teams meeting each other and sharing their work It's going be a very fun series so we can't wait to get more of the Pylon team and our customers involved. Huge thank you to everyone who came out on May 21. It's still mind-boggling to us that people flew in from as far as the East Coast and the UK to be there! See you again at the next one 🫡

AI-pilled? No, Pylon is Tetris-pilled. Oliver (product design) vibe-coded a custom Pylon-themed Tetris game with our brand patterns. Watch everyone try to beat Advith's 20,000 highscore 👀

New in Pylon: HIPAA provisioning per account We've had HIPAA mode in Pylon for a while now, where you can choose stricter email privacy settings for your entire workspace. Now we're adding per-account controls so you can specifically accommodate the customers who actually require HIPAA compliance. For each account... → Go to their account page → Find "Account settings" at the bottom of the sidebar → Change the "Email privacy" settings for that account More granular controls for teams with mixed compliance footprints across their customers!

Usually the logic is that customer onboarding gets worse as you scale. Tighter CSM bandwidth → less personalized setup But our scaled CSM Donal Woods (who manages hundreds of accounts himself) knew that shouldn't be true anymore with AI tools and good account context.... ...so in the past few months he built a Pylonboarding experience that outputs personalized interactive onboarding plans for every customer. This is how the flow works: 1. New customers take a 90-second quiz on their setup status, pain points, and product needs 2. Depending on their inputs, customers automatically get placed into 3 product tracks: Foundation, Growth, or Scale 3. They get a personalized email with track-specific next steps 4. Pylon auto-creates a project for the customer with track-specific tasks 5. Customers get directed to interactive product walkthroughs so they can start exploring Pylon on their own Built with Claude, Pylon, Typeform, Customer.io, and Arcade. Huge shoutout to Dónal for helping scale Pylonboarding while improving the experience for all our new customers. If you're curious to check out one of the interactive product pages: pylonboarding.usepylon.com/a…

From the beginning at Pylon, we've had this conviction that you can't just run B2B support on platforms made for B2C. Why? Account context. Context is everything when your customers... → Are accounts with multiple stakeholders → Sign multi-year contracts → Pay you 6 figures in ARR → Form long-term relationships with your team → Talk to you via unstructured channels like Slack Given the above it's impossible to reduce B2B support interactions to one-time transactions and you can't afford to "forget" customer context and history. This is why we built Account Intelligence. We're the first support platform to connect support data back to account-level context, because we've seen that building up your customer knowledge graph consistently improves outcomes. We partnered with the team at @a16z to prove it with data directly from Pylon. When you maintain and leverage rich context on your accounts, you improve AI-driven resolution and your customers are more satisfied with the support they're getting. We did a whole deep dive on Pylon data and wrote about why contrary to the popular narrative, AI is best as a copilot for support teams and not a replacement for them. Link to the full piece in comments 👇️ — Huge thanks to Jared Forman, our Head of Data, and @saltzman_jason team at a16z for the analysis.

Real quotes from people who churned from Zendesk to Pylon: "After working extensively with industry-standard big-box ticketing systems, it became glaringly obvious that a ticketing tool could be done better." "Our experience with Pylon has validated the decision to leave Zendesk, and I've seen nothing that would cause us to reconsider it." "Pylon has helped us turn support into a system that improves itself." "We're still the same size team, but we're supporting 6x the business volume. Pylon isn't just a tool. It's a partner and a copilot."

Teamwork makes the dream work... ...so we're making it easier to collaborate on tickets. You can now see who else is viewing an issue directly from your list and kanban views. Now it's easier to work through your team's queue together in real-time and there's no more double-handling. Happy collaboration 🤝

New Pylon customization unlocked... Knowledge base themes! You can now fully customize the look of your help center in Pylon: → Edit HTML and CSS directly in a code editor → Preview changes before publishing → Switch between themes in one click We can't wait to see everyone's beautiful knowledge bases 🎨

Just shipped: Queueing logic 🎫 🧠 We added a new ticket queueing logic so you don't have to manually deal with unassigned tickets ever again. When everyone on your team is full or it's after hours, you can now choose for tickets to go into a queue instead of staying unassigned. As soon as the right person becomes available, Pylon will pull tickets from the queue according to priority and assign them a new issue. Link to docs in the comments!