Pylon is the only agentic support platform, purpose-built for B2B companies. For leaders scaling AI-native support teams, Pylon lets humans and agents collaborate on customer work – investigating, resolving, and acting on every signal across every channel that matters.

Unlike platforms built before the AI era, Pylon enriches every interaction with deep account-level context, automates the low impact customer work, and surfaces answers before your team even has to ask. The result: faster responses, happier customers, and a system that continuously improves itself.

We're backed by a16z, BCV, General Catalyst, and Y Combinator. More than 1,500 companies including Linear, Cognition (makers of Devin), Modal Labs, and Incident.io run their support and customer success workflows on Pylon. We're also featured on the Enterprise Tech 30 List.

What You’ll Do 📌

• Bring senior expertise to a motion that's already moving. This is our first San Francisco based SDR leadership hire. SDRs are live, prospecting, and generating pipeline today. Being at HQ, you'll work in close, daily proximity with leadership and your reps, sharpening the playbook and tightening execution on a function that's already running.

• Inherit, hire, and scale the team. You'll take over an existing team of SDRs based in SF and be fully responsible for them including hiring, coaching, and scaling headcount as the function grows.

• Coach and develop. Run 1:1s, call reviews, and pipeline reviews. Train reps on prospecting, messaging, and objection handling. You'll be evaluated on how well your reps improve under you, not just on their output.

• Own team quota. You're held to your team's outbound pipeline targets — meetings booked, opportunities created, and pipeline generated across the team. You won't be booking meetings yourself, but you're accountable for the number.

• Manage performance. Set expectations, track individual and team metrics, and manage performance issues directly.

• Partner cross-functionally. Work closely with AEs on messaging, handoff quality, and feedback loops. Partner with marketing on targeting and campaigns.

• Own the target account strategy. Set the criteria and direction for account selection (150-1000 employees) and ensure the team is prospecting the right accounts, even though you're not building lists yourself day-to-day.

Who You Are 💼

• 2+ years managing an SDR team, ideally at an early-stage startup — required.

• You've hired for and grown a team before, not just inherited one.

• Track record of your team hitting or exceeding pipeline/quota targets — you know how to build a number and hold people to it.

• You can coach: you know how to diagnose why a rep isn't converting and fix it, not just tell them to dial more.

• You've built or meaningfully shaped an outbound motion before — process, messaging, sequencing — even if you're not building from a blank page here.

• Experienced with a modern sales stack (SFDC, Amplemarket or similar engagement tools) and comfortable using data to run the team.

• Strong communicator who can operate with real autonomy — this isn't a hand-holding environment, and you'll have a direct line to our founder.

• (Bonus) Experience selling or managing a team that sold into support / CS / post-sales personas.

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

Traction: Have 1300+ customers and growing fast

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

Founders: Advith Chelikani, Robert Eng, and Marty Kausas

Team: Currently 110 and growing!