Inside a high velocity sales-assisted GTM motion

How Pylon closes up to 30 deals per sales rep each month

May 07, 2025

I got word that an emerging startup was closing as many as 30 deals per sales rep each month. It’s a purely inbound motion, leading reps to close upwards of $2 million in new business ARR per year – for what’s effectively an SMB or commercial sale.

Even more impressive, the gross revenue retention (GRR) on these deals is 95% and net revenue retention (NRR) is 140%. And there are zero sales development reps (SDRs) doing outbound prospecting or lead qualification; it’s all handled by the account execs.

Frankly, it’s extremely rare to see those numbers for an SMB-focused SaaS business. I wanted to learn more – and share the playbook with you all.

The startup is Pylon, a B2B customer service platform which raised a $17M Series A from a16z last August (despite being cash-flow positive). They’re going after Zendesk and have been adopted by more than 500 B2B companies like AssemblyAI, Hex, Hightouch and Incident.io. I sat down with co-founder and CEO Marty Kausas to get the inside story.

👋 Hi, it’s Kyle Poyar and welcome to Growth Unhinged, my weekly newsletter exploring the hidden playbooks behind the fastest-growing startups. Subscribe to join 70,000+ readers who get posts like this delivered straight to their inbox.

The early days: Competing head-on against Zendesk

Marty calls Pylon the first customer support platform for B2B companies. “Support systems today are oriented toward a B2C audience,” he told me. “In B2B you have support, success, solutions engineering, account management. All of these post-sales functions support customers, all of which buy their own separate tools.”

His vision is to build the ‘Rippling-esque’ single platform that can handle it all: ticketing, customer success, customer marketing, AI agents and more.

They’re squarely going up against Zendesk, which generates roughly $2B in ARR and was taken private in 2022 for $10.2B. Well, Zendesk and Salesforce Service Cloud, which generated $9B in revenue last year and is Salesforce’s largest service offering.

As Marty and team were exploring the post-sales market opportunity, they noticed that people were moving away from email for customer communications and into Slack, Teams, Discord and other chat-based platforms. This channel shift appeared to break many existing business workflows, creating an opening for Pylon.

The company’s first customer was Hightouch, which had hundreds of shared Slack channels for their enterprise customers and Intercom for their self-serve customers. The Slack channels had none of the automations or workflows that were available for self-serve customers. Pylon’s initial wedge was around B2B omnichannel support. “In our first year we were essentially a Slackbot for B2B,” Marty admitted.

Part of how Pylon competes against large incumbents is fixing their perception from “6 dudes in a garage” to a successful business

They didn’t think Pylon could initially compete head-on with Zendesk. The founders worried about ‘graduation risk’ – as soon as a customer hired a VP of Support, they’d graduate back to Zendesk. Zendesk getting acquired by private equity changed the equation; now all of a sudden customers weren’t getting the level of service they expected and were open to an alternative.

His advice for other startup founders: pick an emerging trend in a big market, then compete against large, slow-moving incumbents who aren’t focused on a particular niche.

Reaching $1M ARR: Founder-led sales and LinkedIn as the top source of pipeline

Pylon started with founder-led sales and tapping folks within the founders’ existing networks. Their first customer (Hightouch) was actually someone who lived with Marty in a hacker house called Mission Control (no, this isn’t an episode of Silicon Valley). The second and fourth customers were folks the founders had either worked with or been recruited by.

From there, it was a lot of cold direct messages on LinkedIn. Specifically, all three founders would send 40 personalized LinkedIn connection requests per day (the max you could send at the time) asking: “We’re founders who are pivoting, trying to learn about the CS space. Could you give us 15 mins of time to tell us about your work?”

Those DMs paired with warm introductions got Pylon the next 30-50 customers.

Around the middle of 2023, Marty started posting on LinkedIn. “We didn’t know if it would work,” he recalled. “We just started posting and at the time there was no strategy. We only got a few likes per post and one of them was my mom.”

All of a sudden Marty struck gold with a build in public post about going from idea to paid MVP in 17 days. He included a photo of the founders and a detailed breakdown of exactly what Pylon did. This led to a spike in demo bookings and a realization: LinkedIn could be a serious channel.

Marty replicated that same build-in-public formula with stories about:

Living in their office (that was a controversial one, but got 1.2 million impressions)
Pricing (Pylon’s pricing model has changed six times, switching from seats to platform fees and back)
Getting accepted into Y Combinator (it’s 2x as selective as Harvard)
Pylon’s meeting culture (they have zero scheduled meetings)
Even founder salary updates (they started at $35k and steadily raised it as they hit revenue milestones – even though they had raised a $3.2M Seed. Founder salaries are now $115k and they’ve sold $0 in secondaries).

LinkedIn is now Pylon’s biggest source of pipeline based on self-reported attribution when folks book a demo. Marty continues to write all his own first-person and build in public posts. Each of the Pylon co-founders posts every single day from their own accounts with a combination of post styles. The Pylon team has also tested automating LinkedIn connections, testing out LinkedIn video content, cross-posting LinkedIn content to X and Threads.

Marty’s advice: “If you find a growth strategy that works, really milk it. We didn’t follow that advice initially.”

Besides LinkedIn, Pylon has tried cold email and Google ads; neither of them has worked (so far). Word-of-mouth performs well and there’s some natural product virality because once someone installs Pylon, all their customers see Pylon’s name.

Marty and team are currently leaning into their customer success function, which has grown from zero to three people in the last quarter. 25% of net-new revenue came from upsells in Q1.

Sales-assisted GTM: Building a high-velocity (and highly automated) sales motion

Pylon relied on founder-led sales until around $1M in ARR. “Honestly, we waited too long to hire the first AE,” Marty reflected. The first AE joined as Pylon was raising its Series A.

By that time, Pylon had designed a repeatable and high velocity sales motion, which is a hybrid of product-led and sales-led. Let’s call it “sales-assisted GTM”. Here’s what it looks like:

1. It’s all inbound driven. A prospect lands on Pylon’s website and clicks book a demo. Pylon also uses Unify for website visitor → warm outbound sequences. (The inbound workflow is below in case you want to replicate it.)

2. Scheduling is automated. Prospects are routed to an AE’s calendar (which round robins across AEs) and book their preferred time. This is powered by Default.

3. CRM data is automatically created. Each new demo booking triggers a Clay table to fetch account data and contact data, which all gets written into Salesforce. (The CRM enrichment workflow is below.)

4. There’s a demo on the first call. The first call lasts 30 minutes. 15 minutes of the call are for discovery (consultative-feeling); the remaining 15 minutes get to the demo. “We don’t want to waste time, let’s try to solve their problem on the first call.”

5. Qualified prospects immediately get invited to a shared Slack channel. Pylon skips the inbox (“we believe that’s a place where sales conversations go to die”) and moving to Slack allows them to dog-food the product. Pylon now has 1,480 (!) shared Slack channels with customers and prospects. (An example of this is below.)

6. A trial is required – and many jump into a free trial right after the demo. The Pylon rep will send instructions for getting started with onboarding (an AE simply needs to click a button to enable it). These trials are most often one to two weeks; Pylon’s sales cycles last between one to six weeks in total. (For bigger customers, Pylon has a more white glove approach.)

The sales motion is oriented toward velocity and volume – without sacrificing a white glove experience for the customer. Pylon has zero scheduled meetings with the sales team (that’s right, no pipeline review) and to this day Marty has never had a scheduled 1:1 with any AEs.

To put this in perspective, Pylon’s first AE hire currently has 200 open opportunities in their CRM. The second AE hire has been in seat for two months and already has 90 open opportunities.

Pylon’s velocity-orientation is also evident in the company’s approach to onboarding new sellers. By week four, AEs are expected to be fully on their own managing full sales cycles.

Week 1: Seller becomes a product expert equivalent to a support team member. Marty is asking them to watch calls and regularly quizzing them about how to use Pylon.
Week 2: Seller begins shadowing calls. By the end of this week, they lead their own smaller demo calls and Marty is reverse-shadowing them.
Week 3: Seller is mostly let loose. They’re running their own smaller deals and Marty is involved with larger ones.
Week 4: Seller is on their own.

There are trade-offs, too. AEs aren’t hunting for deals because they’re too busy working inbound pipeline. That means Pylon cannot control the types of customers who come in to book a demo. If the team wanted to move upmarket, for example, that’s not something they could control (outside of turning away small customers).

Enabling velocity with GTM tooling

Pylon’s high velocity approach wouldn’t be possible if everything was done manually. They’ve adopted 14 GTM tools to automate things.

Salesforce (sales CRM)
Scratchpad (a Chrome extension that makes Salesforce usable)
Clay (data enrichment in the CRM plus prospecting experiments)
Default (inbound calendar routing)
Salesbricks (modern quoting, signing and billing)
Unify (website visitor to outbound email sequences)
Slack Connect (every qualified prospect gets a Slack channel)
Framer (marketing site builder and CMS)
Arc Browser (split view demo setup)
Assembly (social marketing automations)
Loom (quick videos)
Equals (revenue reporting)
Warmly (live chat on website)
Pylon (used for pre-sales purposes)

Why Salesforce over a more modern CRM like HubSpot or Attio? Pylon’s larger customers used Salesforce and Marty wanted to make sure they understood customers extremely well. “In hindsight we realized the power of the CRM is that it’s the thing that integrates with everything,” he added. “Everyone integrates with Salesforce first.”

Salesbricks was a newer tool (to me) – many folks have historically put off CPQ tools until they’re much larger. It replaced Pylon’s need to have separate workflows for contracts and Stripe links. They can instead create custom quotes and let customers check out and sign at the same time. It’s also allowed Pylon to change pricing models, which they’ve done six times already.

The TL;DR: 5 takeaways from Pylon’s journey

Pylon picked an emerging trend in a big market, then competed against large, slow-moving incumbents who weren’t focused on a particular niche.
They hustled for their initial customers, tapping into existing networks, warm introductions, personalized DMs on LinkedIn and even their own hacker house.
Pylon has turned LinkedIn into their top source of pipeline, striking gold with ‘build in public’ posts from the founders’ profiles.
They built a sales-assisted GTM motion that’s high volume and high velocity – without sacrificing a white glove experience. Each AE closes up to 30 deals per month.
It’s possible to achieve high quotas and high retention rates when selling into the SMB.