☄️ Pylon’s Growth Playbook

Customer support tools were originally built for B2C and then duct-taped together for the rest of us.

Pylon built customer support, for the first time ever, for B2B specifically.

They close 30 deals per rep each month with 95% gross retention and 140% net revenue retention. Even with under 150 employees, they're eating market share from companies 100x their size.

Here's exactly how they built their growth engine:

The LinkedIn Pipeline

All three co-founders post regularly on LinkedIn, with CEO Marty Kausas batch-writing weekly for 5+ hours on Sundays.

Specific examples that drove the pipeline:

• Paid MVP in 17 days post → immediate demo requests

• "Living in our office" post → 1.2M impressions

• Pricing iterated 10 times → public transparency that builds trust

As a result, LinkedIn is the #1 source of inbound for Pylon.

They treat all their founders' personal LinkedIn accounts as core growth channels. They work to remind you over and over again that they exist.

Sales Process Engineered for Velocity

Pylon runs a sales-assisted, inbound-only motion with no SDRs. This is unheard of for companies selling primarily to businesses.

AEs handle 200+ opportunities at a time while following a compressed, standardized flow:

• Instant demo booking: With the help of Default, prospects are routed to an AE's calendar

• 30-minute first call: 15 min discovery + 15 min demo

• Slack-first follow-up: Qualified prospects enter shared Slack channels immediately; Pylon manages 1,480+ Slack Connect channels with prospects/customers

• Mandatory trials: 1–2 weeks, started during that first call

• Asynchronous ops: No scheduled pipeline reviews or 1:1s for AEs

As a result, they have 1–6 week sales cycles, even for larger deals. By removing handoff friction, combining steps, and meeting buyers in the channels they already use (Slack/Teams) they shorten cycles.

Building for Inevitable Expansion

Pylon designed its entire business model around expansion revenue. In one quarter, 25% of net-new revenue came from existing customers.

Their expansion strategy has three pillars:

1. A product that spreads naturally

When one team adopts Pylon, adjacent teams notice. The tool becomes the connective tissue between departments and creates organic expansion opportunities.

2. Fast time-to-value

Migrations happen in days. Sardine moved 120,000 tickets from Zendesk in 5 days. OneSchema consolidated its scattered Slack support into one system within a week. Fast implementation means customers see ROI before the first invoice arrives

3. Proactive account management

They grew Customer Success from 0 to 3 people in one quarter before they "needed" it. These CSMs identify expansion signals: team growth, feature requests, usage patterns. Then they act on them immediately.

The results prove the model:

• AssemblyAI: 97% faster responses, 50% of tickets resolved by AI

• Hightouch: Managing 300+ Slack channels, 75% self-service rate

By building expansion into your product DNA, you allow for fast onboarding, natural virality, and proactive CS which lead to compound growth.

Bottom Line

Pylon's growth strategy boils down to five moves anyone can steal:

1. Pick a niche the giants ignore

Zendesk and Salesforce built for B2C support (high volume, simple tickets). Pylon noticed B2B companies were jerry-rigging these tools for complex, relationship-driven support across Slack and Teams. They built specifically for that gap.

2. Make founders your marketing department

Instead of hiring marketers, the three founders post daily on LinkedIn.

Cost: 5 hours of CEO time weekly.

Return: #1 growth channel. Seems worth it.

3. Turn Customer Success into a growth engine

They hired CS before they "needed" it. With the right systems (unified queue, AI automation, account intelligence), three CS people can drive 25% of new revenue.

4. Delete friction, not quality

No SDRs doesn't mean no sales pipeline, but rather automated scheduling and qualification. Every piece of friction they removed was replaced with a system that works better.

The constraint on growth isn't talent or capital. It's the systems that allow talent to operate at full capacity.

Every company says it moves fast. Pylon built the systems to actually do it.

David Lobo

Head of Growth, Workmate

P.S. What's the biggest operational friction slowing your team down right now? Reply and let me know.

P.P.S. Building high-velocity systems starts with eliminating low-leverage work. That's why we built Workmate—to handle scheduling automatically so you can focus on work that actually moves the needle. Join the waitlist.