Head of Engineering

At Pylon, we're building the future of B2B Post Sales.

We're building the all-in-one B2B post-sales support platform powered by conversational data and layered with intelligence to help our customers run their operations in real-time.

We're backed by a16z, BCV, General Catalyst, Y Combinator.

Currently more than 1000 companies including Linear, Cognition (makers of Devin), Modal Labs, and Incident.io run their support and customer success workflows with Pylon. You'll also find us on the Enterprise Tech 30 List.

We're at ~90 people and growing fast. Engineering is the engine. We need a Head of Engineering who can keep it running at speed without letting quality slip - someone who's as comfortable in the code as they are setting the technical and product direction for the next two years.

What you'd be walking into..

• A technical team of ~25 senior engineers built from alumni from fast-growing startups

• A product surface that's growing fast with a lot still to build

• An AI-native product, where many features are AI features and many features were built with AI

• An org that's outgrown some of its processes and needs someone to build the next layer of infrastructure - team structure, hiring cadence, engineering rhythm, product vision - without slowing down velocity

You might be a fit if the below describes you...

• You've scaled an engineering org through a hypergrowth phase - you know what breaks, what to build ahead of, and how to structure teams before the org chart forces your hand

• You have strong product instincts. You push back on prioritization when it's wrong, have opinions on what to build, and don't just execute what's handed down

• You coach engineers and managers with clarity, high expectations, and genuine investment in their growth

• You set a high hiring bar and you hold it. You'd rather leave a role open than fill it with someone who doesn't raise the room

• You're obsessive about shipping velocity without letting quality become the casualty. You know the difference between technical debt worth taking and the kind that kills teams

• You communicate clearly and early with founders

• You're in SF or willing to relocate and are excited to work in-person

• Our stack is React, Golang, GraphQL, and AWS

The background we're imagining you might have...

There's no single path that gets you here. We're open to:

• A current or former Head of Engineering at a fast growing startup

• A Director or VP of Engineering at a slightly larger company - someone who still has startup DNA and hasn't spent their career in a big org

• A Senior Engineering Manager who's been leading teams of 10+ engineers across multiple teams for several years and is ready for a step up

• Or an entirely different background if you can make the case for it...

What we're not looking for: someone whose entire career has been at large companies, or who hasn't been close to the code since the early days. The founding team is technical and will expect you to keep up.

What you'll own

• The full engineering org - hiring, performance, onboarding, and manager development

• Technical roadmap and architecture, in close partnership with product and the founders

• Engineering velocity and quality - releasing fast and with confidence

• Cross-functional relationships with Product, Support, CS, and Sales

• Org design and capacity planning as we scale from ~90 to well beyond

Our perks

🏥 Fully covered medical, dental, and vision insurance for employees

🏦 401(k) retirement plan

🚆 Commuter benefits

🌱 Parental leave

🏝️ 14 company holidays + unlimited PTO

🗺️ Annual offsite

🍽 Lunch, dinner, and snacks at the office

🏋️ Fitness stipend

More about Pylon

Funding: Series B led by a16z and BCV ($51M total raised)

Founders: Advith Chelikani, Robert Eng, and Marty Kausas

Team: Currently 90 and growing!