Pylon

Head of Engineering

Pylon1 weeks ago
Location

San Francisco

Type

Full Time

Salary

USD 250,000 – 400,000

Level

Director

Role

Head of Engineering

Posted

Mar 24, 2026

Full TimeDirector

The role

Summary

Pylon is seeking a strategic Head of Engineering to lead and scale their rapidly growing B2B post-sales support platform. The ideal candidate will drive technical innovation, manage a high-performing team of 25+ senior engineers, and maintain exceptional product velocity while ensuring engineering excellence in an AI-native startup environment.

What you'll do

Engineering Organization Management: Lead full engineering org including hiring, performance management, onboarding, and manager development
Technical Strategy: Define and execute technical roadmap in partnership with product and founders
Team Performance: Drive engineering velocity and quality, ensuring rapid and confident product releases
Cross-Functional Collaboration: Build and maintain relationships across Product, Support, Customer Success, and Sales teams
Organizational Scaling: Design org structure and capacity planning as company grows from 90 to well beyond

What we look for

Technical

Technical LeadershipAbility to maintain technical quality while driving rapid product development
Architecture DesignExperience in designing scalable software architectures

Education

Computer ScienceBachelor's or Master's degree in Computer Science, Software Engineering, or related technical field preferred

Experience

Engineering LeadershipMinimum 7-10 years of engineering experience with 3-5 years in leadership roles
Startup ScalingProven track record of scaling engineering teams through growth phases

Skills

Required skills

Engineering LeadershipProven experience scaling engineering organizations through hypergrowth phases
Technical StrategyAbility to set technical roadmap and architectural direction
Team DevelopmentStrong skills in coaching, mentoring, and developing engineering talent

Nice to have

Startup ExperienceBackground in fast-growing technology startups with strong startup DNA
AI Product DevelopmentExperience with AI-native product development and implementation

Compensation & benefits

Salary

USD 250,000 – 400,000 (annual)

Stock options

Available

Benefits

Medical Insurance

Fully covered medical, dental, and vision insurance

Retirement Plan

401(k) retirement plan

Commuter Benefits

Commuter benefits program

Parental Leave

Comprehensive parental leave policy

Paid Time Off

14 company holidays + unlimited PTO

Annual Offsite

Company-sponsored annual offsite event

Meal Benefits

Lunch, dinner, and snacks provided at the office

Fitness Stipend

Fitness and wellness stipend

Interview process

  1. 1
    Initial Screening — Preliminary discussion with recruiting team to assess background and fit
  2. 2
    Technical Leadership Interview — In-depth interview focusing on engineering leadership experience and strategic thinking
  3. 3
    Founder Interview — Discussion with company founders to evaluate alignment with company vision
  4. 4
    Team Interaction — Collaborative sessions with current engineering team members
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Pylon

Pylon

View all jobs

Pylon is a platform that helps businesses automate and optimize their customer communication and support operations. The company provides tools for managing customer interactions across multiple channels, enabling organizations to streamline workflows, improve response times, and enhance customer satisfaction. Pylon serves businesses of various sizes looking to modernize their customer engagement infrastructure and gain better visibility into their support operations.

San Francisco, USAFounded 2022usepylon.com

Tech Stack

Languages
Golang
Frameworks
React
Tools
GraphQLAWS
Other
AI Technologies
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