Head of Engineering

Appsierra Group; San Francisco (CA); On-site; USD 200,000 - 300,000; Full time

Benefits offered by this job

Founding scope

CTO path

Platform building

Deployment impact

Enterprise leverage

Fortune 5000 access

System impact

Job summary

Appsierra Group seeks a Head of Engineering to lead the core platform and multiple client-implementation teams from San Francisco. You will drive technical direction as the company scales and ensure delivery excellence across engagements.

You will mentor engineers, define architectural standards, and stay hands-on for critical decisions. A direct path to CTO awaits the right leader in a high-impact environment.

Qualifications

• 6+ years software engineering, with proven leadership of engineers or teams.
• Experience delivering across multiple teams or workstreams.
• Deep production experience with AI agents, orchestration, retrieval, and human-in-the-loop.
• Strong distributed-systems instincts and enterprise integration experience.
• Hands-on with APIs, OAuth, connectors and multi-cloud deployments.
• Ability to own infrastructure, release management, and on-call duties.

Responsibilities

• Lead core platform and client-implementation teams, aligning platform and implementations.
• Partner with product owners to run several engagements concurrently.
• Recruit, mentor, and grow engineers and future leads.
• Set code review and reliability standards for scale from 5 to 50.
• Define architecture and technical bar across platform and implementations.
• Oversee build-vs-buy decisions and productionizing agent frameworks.
• Guide teams building multi-step agent systems and orchestration.
• Own multi-client fleet infrastructure across cloud and on-prem deployments.
• Lead fleet upgrades, rollbacks, monitoring, and on-call readiness.
• Lead Kubernetes, IaC, and multi-cloud strategies (AWS/GCP/Azure).

Skills

Leadership

Distributed systems

AI agents in production

Multi-team delivery

Kubernetes

Cloud architectures

Job description

Head of Engineering

Location: San Francisco, CA
Employment: Full-Time
Experience: 6+ Years
Salary: $200,000–$300,000 per year
Visa Sponsorship: None Available

About the Role

The Head of Engineering leads engineering across the core platform and client implementations, partnering with product owners to run multiple engagements simultaneously and defining the technical direction as the company scales from 1:1 client engagements to 1:many.

This is a high-impact engineering leadership role with responsibility for the technical architecture, engineering organization, platform reliability, and delivery across every client environment.

You will set the technical bar, grow and mentor the engineering organization, and remain hands‑on enough to make critical technical decisions and step in where it matters most. The role has a direct path to CTO.

What You'll Own

• Lead the core platform team and multiple client-implementation teams, owning the seam between the platform and implementations

• Partner with product owners to run several engagements simultaneously

• Recruit, mentor, and grow engineers and future engineering leads

• Set code review and reliability standards and build an organization that scales from 5 to 50

• Define architecture and the technical bar across the platform and every implementation

• Make build‑vs‑buy decisions and translate developments in agent frameworks, tool use, and long‑context reasoning into production

• Guide teams building compound agent systems, including multi‑step orchestration, retrieval, structured extraction, evaluation suites, and confidence‑gated human‑in‑the‑loop

• Own the multi‑client fleet and infrastructure across shared‑cloud, dedicated, VPC, on‑prem, and air‑gapped deployments

• Own fleet‑wide upgrades and rollbacks, monitoring, alerting, and on‑call

• Lead Kubernetes, infrastructure‑as‑code, and multi‑cloud environments across AWS, GCP, and Azure

Must-Have

• 6+ years of software engineering experience, including real‑time experience leading engineers as a lead, manager, or founding engineer accountable for a team's output

• Proven engineering leadership, with experience building, growing, and mentoring engineering teams and owning delivery across multiple teams or workstreams simultaneously

• Deep experience building and shipping AI agents in production across orchestration, tool use, retrieval, structured extraction, evaluation, and human‑in‑the‑loop—not just prompt demos

• Strong distributed‑systems instincts, with depth in multi‑tenant backend systems, data modeling, and enterprise integration

• Experience working with real APIs, OAuth, connectors, and enterprise ERP and CRM software

• Comfortable owning infrastructure, including Kubernetes, infrastructure‑as‑code, and multi‑cloud

• Experience operating software across many deployments and versions, including release management, staged rollout, rollback, monitoring, alerting, and on‑call

Nice to Have

• Forward‑deployed or customer‑facing engineering experience, including direct interaction with the people whose processes are being automated

• Background in process mining, workflow automation, or enterprise process discovery

• Previous founding engineer or CTO experience at a venture‑backed startup

• Experience operating in enterprise environments with real security, compliance, and reliability requirements, including SOC 2, audit, and on‑call/incident response

• Published research or open‑source contributions in agents and applied AI

Benefits & Perks

• Founding team scope and ownership of the entire technical vision

• Direct path to CTO

• Opportunity to build a platform, not just features

• 100% deployment rate with immediate measurable impact

• Compounding leverage from every client deployment

• Direct access to Fortune 5000 decision‑makers

• Opportunity to work on systems that improve with every customer

Interview Process

1. Pending Approval

2. Vibe Check

3. First Round

4. Second Round

5. On Site

6. Offer

7. Hired