Pylon

Building the next generation support platform, built for B2B companies.

Backed by a16z, General Catalyst, Y Combinator

Customer Support, also Co-Founder & CEO

Andreessen Horowitz

Investing both personally and most recently through a16z's scout fund.

Angel Investor

Airbnb

Software Engineer

Clipboard Health

Freelanced at Clipboard while working at Airbnb for fun.

Kleiner Perkins Caufield & Byers

Engineering Fellow

Purdue Hackers

President

BoilerMake

Hackathon Organizer

Purdue University

Undergraduate Lecturer CS 190: Tools and Resources

Undergraduate Lecturer CS 490: iOS Development in Swift

Yelp

Software Engineering Intern

Qualcomm

Building the Zendesk Killer.

Pylon is the next-generation support platform, optimized for B2B companies.

Backed by a16z, General Catalyst, and Y Combinator.

Half the company came into the office on Saturday.

I made a deal with 🌶 Bennett Amodio that if the team collectively did 4000 pull-ups in 8 hours, we'd add a monthly fitness stipend to our benefits.

So Bennett rallied people to train for two months leading up to the Pylon Pull-Up Challenge. 

The team absolutely shattered the goal with...

→ 4012 pull-ups
→ 23 participants 
→ 6 hours
→ 2 pull-up bars

...and most importantly, everyone had a fun time gathering and cheering each other on.

If you're looking for a new role, we're hiring! We offer great benefits, now including $150 each month to spend on personal fitness. 

Link to apply in the comments 👇

Marty Kausas

We raised Pylon's $31M Series B in 7 days.

We didn't need the money.

And we weren't fundraising.

We were focused on supporting customers, building product, and selling.

But investors expressed interest.

...and word spread fast 🔥🔥🔥

Within 7 days we signed a term sheet with a16z and Bain Capital Ventures.


-- Company --

- Pylon was 2 years and 7 months old
- We had 4.5 years of runway.
- We had only burned $3M of $20.3M previously raised
- Team was 37 people


-- Exact Timeline --

During the weeks leading up to the raise, I started accepting requests for coffee chats at Pylon. I'd chat with investors for 30m where I'd talk about Pylon, hear about their firm, and then talk about our fundraising plans. I'd share "we're not fundraising but if someone were to give us $30M at $XXXM valuation, we'd be interested".   

July 4th - We decide we're going to raise, quickly
July 4th-10th - Many investor conversations
July 10th, 8AM - Partner presentation for BCV
July 10th, 1PM - Verbal offer from BCV
July 11th, 10AM - Partner presentation for a16z
July 11th, 11AM - Verbal offer from a16z
July 11th, 11PM - Term sheet signed


-- Fundraising History --

Jan 2023 - Pre-Seed from Y Combinator ($125K raised, $1.79M val) 
Mar 2023 - Seed led by General Catalyst ($3.2M raised, $20M val)
July 2024 - Series A led by a16z ($17M raised, $90M val)
July 2025 - Series B led by BCV & a16z ($31M raised, 🤫 val)

This brought total raised to $51M.


-- Notes --

- Why raise? a) signaling to prospects, customers, and employees and b) there's downside to not raising after getting inbound interest. We asked ourselves "would we get better terms in 6 months when we expected to raise?" and the answer was "no". Delaying the raise introduced risk if we started to perform worse over the coming months or if market conditions worsened.

- Why only $31M? We didn't need the money and wanted to minimize dilution. 

- We decided to run our Series B process the same way we ran our Series A process: a) build a great company then b) let investors come to you. If you don't need money you have leverage. In comments see one year ago how we raised our previous two rounds.

- Compared to early stage investors (up to Series B), growth stage investors (Series B+) are very different. Early stage think more about potential while growth funds are more focused on actuals and numbers. Part of what we loved about BCV and continuing to work with a16z is that they were able to do both well.


🎥: Advith, Robert, and me ubering over to BCV's office. We didn't need to prepare much for the presentation itself. The work that mattered (building the company) had already been done. Fundraising meant cashing that hard work in.


-- What is Pylon? --

We're building the first support platform purpose-built for B2B.

People call us the Zendesk killers.

Yes, it's filled with useful AI.

Check us out 👇️ 
usepylon.com

Pylon is hiring a Head of Marketing.

You'd be joining an absolute rocket ship 🚀

Team: 
↳ Company 3x'd this year (so far)
↳ Former YC founders, staff/senior folks
↳ Marketing still small (5 people)

Product
↳ SaaS + AI
↳ 4 SKUs (3 are AI)
↳ Multi-product strategy

Growth
↳ ARR (can't share but it's 📈)
↳ 166% NRR
↳ 94% GRR

Market
↳ Customer support market is massive
↳ Weak incumbents Service Cloud ($9B) + Zendesk ($3B)
↳ Ripe for AI disruption

Investors
↳ Bain Capital Ventures (Series B)
↳ a16z (Series A)
↳ General Catalyst (Seed)
↳ Y Combinator


We want someone who is...
↳ Demand gen focused
↳ Boots on the ground
↳ High urgency
↳ Metrics driven
↳ Has great "taste"
↳ Crazy enough to think they can build a generational company
+ Bonus for having a LinkedIn presence 

JD here: 
https://lnkd.in/gDZ25PYa

No alternative text description for this image

Introducing... 🔍 AI Knowledge Assistants 🔍

Maintaining your help center is notoriously hard. It contains a LOT of content, your product is constantly changing, and new team members don't have context into your existing content. 

Now, AI Knowledge Assistants will automatically keep your articles up to date. 

Here's how it works...

1/ AI continuously scans your support interactions to identify missing or outdated topics in your knowledge base.

2/ If a topic is missing, AI drafts a brand new article based on how you've responded to past customer issues.

3/ If a topic needs an update, AI drafts edits to an existing article and you can review before publishing.

Instead of knowledge base hell, you now have a help center that writes itself. 


—

Shoutout to Anish Kachinthaya for absolutely crushing this project (and for giving a great explanation of how it works).

Q4 board meeting ✅️ 

First, we walked through highlights and lowlights of Q3...

🟩 Revenue growth
🟩 Product velocity
🟩 New leaders
🟩 Team growth

🟨 Working as one company vs individual teams
🟨 Evolving culture with a fast growing team
🟨 Creating scalable process with a fast growing team


Key themes we discussed moving forward:

→ Pylon is positioned to win the B2B support market. It's about execution now. 

→ We as founders need to evolve how we spend our time and learn how to better manage and lead.

→ We'll want to plant market expansion seeds over the next two quarters



Thank you Niko Bonatsos (General Catalyst), Merritt Hummer (Bain Capital Ventures), Jennifer Li (a16z), Andy McCall (a16z), and Eric Zhou (a16z) for all the hard work.

The secret behind our product process?

It's still founder-led by Robert and Advith. 

They are deeply involved in every step.

They...

→ talk to customers (3-4 calls / day)
→ participate in design reviews (weekly)
→ understand business context (market)
→ work directly with design, eng, support, CS, sales

So many companies hand off product early on but we've seen it as so critical that it's one of the last things we wanted to hand off.

That said... given our multi-product vision, we need PMs to join the team.

If you'd like to work directly with founders and eventually have me post about you on LinkedIn...

Apply! JD in comments.


-- Notes --

- They are helped by working with an absolutely cracked design team (Wendy, Oliver, Ben) and engineers, with no middle-men in-between.

- Do I as CEO get involved with product decision making? Almost entirely no. The honest reason is Advith and Robert are way better at it than I am. I learned this the hard way at the start of the company. For almost every debate we'd have about product, they would have the right intuition on what made sense. It's truly incredible to watch and results in almost no throw away work for our team.

One. Day. At. A. Time.

Pylon was built over many days and it's working.

We've built the first support platform built for B2B.

We replace products like Zendesk, Intercom, and Salesforce Service Cloud, along with adjacent products (e.g. Customer Success Platforms).

Join us: https://lnkd.in/gmcYnSnd

-- Notes -- 

- The actual chart start date should be 11/23.

- Each color is coded by year so you can see expansion within each cohort of customer closed within that year.

Introducing... AI Ticket QA

We're not just killing Zendesk, we're killing your QA platform too. 

Before, support managers manually reviewed tickets to evaluate team performance.

Now, AI Ticket QA does it automatically AND better.  

Here's how it works...

1/ Tell AI your expectations for tone of voice, customer sentiment, PII compliance, product knowledge, or other criteria.

2/ In one view, see how each issue is scoring against your rubrics.

3/ Get a breakdown of where team members and AI Agents are doing well, and where they can improve.

We see this replacing manual workflows, a lack of QA processes, or tools like SupportLogic and MaestroQA. 

It's a big release and we're excited for you to try it.

Link to docs in the comments 👇️

Today we're releasing our most requested feature...

💌 Email Broadcasts 💌

Broadcasts allow you to send product updates and outage notifications directly to your customers. 

Up until this point we supported broadcasts via Slack and Microsoft Teams. But it's always been a gap that we didn't support sending them via email. 

Here's how it works...

→ Write and format your announcement once
→ Filter audience by accounts, tiers, or contacts
→ Preview the email
→ Hit send

One more part of your customer operations stack that can now live out of Pylon.

CEO @ Pylon | B2B Support Platform

Matthew Hafizi

Last week we accidentally were #7 on Product Hunt.

Someone decided to launch Pylon and got us featured on the homepage. 

We weren't expecting this at all but thank you for the love 🫶

If enough people follow along, we'll keep posting our product launches there: https://lnkd.in/gMhBCJrk

Happy Monday! Remember "B2B Support = Pylon"

Had a chance to share the how Advith, Robert, and I started Pylon at Notion's conference.

See the full recording here: https://lnkd.in/g-cqz-Yi

HockeyStack's customer base grew faster than they could scale headcount.

As the team landed more enterprise clients, CSMs and data analysts were spending hours manually gathering context before each customer interaction.

They needed AI that would unblock internal processes, not just deflect tickets. 

So they used Pylon to transform their post-sales operations...

→ Improved ticket resolution times with automated triaging
→ Faster ticket prioritization using workflows and triggers
→ Eliminated manual work with context summarization

Now that AI does the heavy lifting, the team can focus on strategic account growth for more customers.  

Thank you Buğra Gündüz, Sunil Joseph, and the HockeyStack team for being incredible partners 🚀

Whose content do you like more?

Chungin Lee's or mine?

Happy Halloween! This marks the end of another huge month at Pylon 📈🎃

𝗕𝗶𝗴 𝘁𝗵𝗶𝗻𝗴𝘀 𝘄𝗲 𝘀𝗵𝗶𝗽𝗽𝗲𝗱...

→ AI Web Research
→ Hierarchical Accounts
→ Custom Domains for Customer Portal
→ Custom Call Recorder API
→ Skills-Based Routing
→ and so much more

𝗠𝘆 𝗳𝗮𝘃𝗼𝗿𝗶𝘁𝗲 𝗰𝘂𝘀𝘁𝗼𝗺𝗲𝗿 𝗹𝗼𝘃𝗲...

"Thanks for helping us 10x our support function - we're proud Pylon customers!"

"I swear everything you all build is magic"

"Speed at which your team is moving doesn’t go unnoticed."

"Thank you 2 huge features that are super helpful for us!  AI Web Research (HUGE) and Skills Routing. Thank you!!!"

"Our Ops team absolutely loves the Pylon product and can’t live without it anymore."

"Just wanted to say how awesome your tool is, we are absolutely loving it. At times it feels like magic. It's that rare situation where the tool is so good it changes the way you work for the better. We are seeing faster response times already. Major props to building such a game changer! 💪"

"WOOHOO! This is amazing! Best early birthday present I could have asked for"

"You guys pop up on more and more of my vendors - surely you must be tired of taking over the world by now 🙂"

"Congrats on what you've done with Pylon... I've played around with the platform it's like Intercom but without the fluff"

"The Pylon team has been awesome to work with. They’ve been super responsive and really hands-on in helping us figure out how to get the most out of both the chatbot and the rest of the platform."

"I've been really impressed with Ask AI so far with gong calls, tickets, slack channel context."

"Intercom is a tool of the past Pylon is the future"'

"Love what you guys are building and how you are building it!"

"wanted to shoutout how Teams and Sub-teams work together flawlessly. Took me maybe 15 minutes to setup something that takes many many hours of work to setup and validate on Zendesk."

"I am able to ramp up my CSE in like 3 days because of great features like Ask AI on the issue sidebar. Absolutely clutch, it not only speeds up time to respond to tickets for new hires but is able to provide passive knowledge upskilling. Great job Pylon, enjoy the summit!"

"We love working with your incredible team."

"we love you guys! Used the Broadcast feature this week for the first time and it was 🔥🔥"

"Success! The new trigger works excellently, and I already have a few ideas to take this further. This will save me so many clicks!"

"I LOVE the product"

"mate your product is kicking ass! Love all the product releases."

Pylon is evolving into an autonomous platform.

Our customers are building absolutely crazy AI workflows...

→ Handle Support Volume (Support Agent)
→ Self-Correcting Help Center (Knowledge Assistant)
→ Route Tickets (AI Router)
→ QA Tickets (QA Agent)
→ Detect Anomalies (Anomaly Agent)
→ Churn Signals (Account Intelligence)
→ Upsell Signals (Account Intelligence)
→ Summarize Accounts (Account Intelligence)

And all of these AI products work in tandem off of the same data. 

It's magical to see ✨️

Pylon's AI Agents save Retell AI 15 hours/week.

As they scaled to 200M+ calls, engineers were spending their time collecting call IDs, gathering context, and routing tickets instead of actually debugging.

So they built AI agents in Pylon. 

Now when there's a voice issue, our AI agent grabs the call ID, pulls logs via API, and hands it over with context. Engineers skip straight to problem solving.

Results...
→ 80% of L1 tickets automated
→ 50% of L2 tickets prepped by AI before handoff
→ 12-15 engineering hours per week back to product work
→ No more back and forth for basic info

...and engineers get to focus on engineering again. 

Thanks for being great partners Prabir Vora and the Retell AI team!

Retell AI

Founding Technical Chief of Staff, Retell AI (YC W24)

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