Head of Support

About the role

You will architect and own the end-to-end support strategy for a B2B AI platform, defining the future of human and agent collaboration across every customer touchpoint. This role requires you to establish the operational DNA of a global support organization, balancing high-velocity execution with long-term strategic systemization. You will act as the primary architect of the customer experience, ensuring that every interaction leverages deep context to drive resolution and insight. The position demands comfort with ambiguity as you build processes that do not yet exist, turning the evolving nature of AI support into a core competitive advantage. You will be responsible for aligning support outcomes with product, sales, and customer success to create a unified go-to-market engine. Success in this role will be measured by the quality of the system you build, the autonomy of the leaders you grow, and the trust you establish with both customers and executive leadership. You are expected to operate at the intersection of data, empathy, and product intuition, ensuring that support is a driver of retention and expansion.

Key facts

What you'll do

Define how AI changes support at Pylon, determining ownership boundaries, automation scope, and the resulting team structures, workflows, and career trajectories.

Own the operating cadence for response times, resolution times, quality metrics, escalations, and customer sentiment as the customer base scales in complexity and volume.

Build the foundational systems support operates on, encompassing knowledge management, quality assurance, onboarding, incident response protocols, and capacity planning, each with a designated owner and a recurring review rhythm.

Serve as customer zero for Pylon's workflows, driving dogfooding initiatives across the support team and owning the feedback loop that converts support interactions into product insights and roadmap input.

Lead the development and expansion of support across the US and EMEA regions, establishing the New York team and ensuring standards remain unified despite geographic fragmentation.

Grow team leads and managers, designing levels and career paths that enable day-to-day execution to be managed independently of your direct involvement.

Evaluate the viability of a support-led revenue opportunity for Pylon, analyzing customer demand and making data-driven decisions on productization based on actual customer behavior.

Establish governance over the support technology stack, ensuring integrations, APIs, and logs are understood well enough to troubleshoot deeply and advocate effectively for engineering improvements.

Champion a high-agency, low-ego culture by presenting strategic plans to the leadership team and simultaneously handling intense, escalated ticket investigations without losing operational perspective.

Ensure that support processes are resilient to turnover, creating durable systems that absorb change and maintain quality regardless of team composition.

Maintain a rigorous understanding of the metrics that matter, translating raw data into actionable changes that improve response quality and customer happiness on a continuous basis.

Balance proactive and reactive work, shifting capacity between firefighting and strategic improvement based on real-time signals from the customer base.

Model curiosity and technical fluency, engaging with engineering partners to understand integrations, logs, and tradeoffs to diagnose root causes rather than simply routing escalations.

Act as the primary voice of the customer internally, ensuring that frontline insights directly influence product decisions, go-to-market strategy, and long-term vision.

Requirements

You have led and scaled a technical B2B support organization, with prior experience at dev tools, infrastructure, API, or data companies providing the necessary context for this role.

You have built systems and teams from scratch, demonstrating the ability to transform recurring pain points into owned, measurable processes rather than relying on one-off fixes.

You possess technical fluency that allows you to reason about integrations, APIs, logs, and engineering tradeoffs without needing to be a hands-on engineer, enabling deep collaboration with technical partners.

You hold a clear, opinionated perspective on how artificial intelligence is reshaping support, backed by tangible evidence of what you have built or shipped in a support or product capacity.

You operate with high agency and low ego, comfortable moving between strategic presentations to the leadership team and hands-on investigation of escalated customer issues.

You maintain a high standard of excellence while preserving trust during difficult conversations, balancing empathy with accountability in conflict resolution.

You are comfortable making decisions with incomplete information and rapidly iterating on processes when initial hypotheses prove incorrect.

You have a track record of ownership that extends beyond your direct scope, including cross-functional coordination and the removal of blockers that span multiple teams.

Nice to have

Experience launching a new support location or regional team, ensuring standards are maintained while adapting to local expectations and regulations.

Experience building structured dogfooding and product feedback systems that close the loop between customer usage and product development.

Experience operating in fast-changing, founder-led environments where process is invented in response to real-time needs rather than theoretical frameworks.

Practical notes

This role is full-time.

The position is based in San Francisco.

Travel is not required for this role.

Visa sponsorship is available for roles that require it.

This role does not have an application deadline.