Head of Engineering
$200k - $300kAppsierra Group
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
Pending Approval
Vibe Check
First Round
Second Round
On Site
Offer
Hired
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