Head of People

About the role

You will own the end to end People strategy and execution for a Series B scale up that is defining how B2B support operates with AI. You will design and drive the people ops systems that allow the company to move fast without breaking as it multiplies in size. You will be the architect of performance management, compensation, and career frameworks that translate company values into daily behaviors. You will build recruiting and hiring processes that source and close high caliber technical and customer facing roles in a competitive market. You will partner directly with founders to align org design, leadership calibration, and promotion practices with business milestones. You will steward the culture by interpreting core values and ensuring they are lived, not just stated on a website. You will be a player coach who is comfortable diving into operational detail while maintaining a strategic view of the business.

Key facts

What you'll do

Investigate and own the full scope of people operations including HRIS, equity administration, benefits, broker management, and immigration counsel.

Design and run the end to end employee lifecycle from onboarding and 30 60 90 plans through offboarding, payroll coordination, and compliance.

Own performance and compensation programs by setting comp bands, review cycles, promotion criteria, and PIP processes.

Build and manage the recruiting function including headcount planning, sourcing channels, interview flow design, and offer negotiation.

Partner with founders and leadership to define org design, staffing models, and hiring plans that scale the company tenfold.

Define and drive the employee experience by translating cultural values like Sprint the Marathon, Happy Grinder, Product Fluency, and Win as a Team into behaviors and rituals.

Establish learning and manager enablement programs that develop coaching skills, feedback practices, and career pathing.

Be the primary owner of culture, monitoring signals, running pulse checks, and intervening when culture diverges from stated values.

Own the tools and processes that scale people work, choosing and implementing HRIS, ATS, and productivity systems that support a high bar operation.

Act as a hands on leader who is willing to do the grunt work of building processes, documenting playbooks, and closing hard hires.

Own the analysis and reporting on headcount, diversity, retention, and engagement metrics to guide leadership decisions.

Represent the People function externally by managing relationships with legal, payroll, and benefits providers in the San Francisco market.

Champion data informed decision making while balancing empathy, fairness, and the realities of a fast growing startup.

Ensure all programs are built with scalability in mind so that the function can evolve smoothly as the company grows to the next stage.

Requirements

You have actively scaled People organizations from around 50 to 500 employees in a fast growth environment.

You have hands on experience with payroll, benefits, equity plans, and compliance in a US based company.

You have run performance and compensation cycles, built comp bands, and managed promotion and calibration processes.

You have personally handled employee relations situations including PIPs, investigations, and terminations.

You have built recruiting processes and pipelines, managed sourcers and recruiters, and closed offers in a high pressure environment.

You have implemented HRIS systems such as Workday, Rippling, or similar and integrated them with ATS and payroll tools.

You have lived the grind of doing the work yourself before building teams and can explain the details of how the business operates.

You prefer a high bar for execution and clarity in communication, and you model these behaviors in your day to day work.

Nice to have

Experience in a B2B SaaS environment where support and customer success workflows are core to the product narrative.

Familiarity with agentic workflows, AI tooling, and how emerging technology impacts the future of work.

Practical notes

This role is full time based in San Francisco.

Travel is not expected as part of this role.

Visa sponsorship is not available for this position at this time.

The candidate must be able to start within a tight timeline aligned with the next batch of hiring pushes.

More about Pylon

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 is faster responses, happier customers, and a system that continuously improves itself.

We are 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 are also featured on the Enterprise Tech 30 List.

Our perks

Commuter benefits, Parental leave, 14 company holidays plus unlimited PTO, Annual offsite, Lunch dinner and snacks at the office, Fitness stipend.

Founders

Advith Chelikani, Robert Eng, Marty Kausas.

Team

Currently 100+ and growing.