VP of Engineering at Series A Startup

About OnRamp

OnRamp transforms B2B customer onboarding into a revenue driver. Our platform automates workflows, streamlines playbooks, and accelerates time-to-value, helping enterprises reduce onboarding time by up to 70%. Backed by leading investors (we just raised our $15M Series A) and trusted by Fortune 15 companies, we’re redefining how companies bring new customers online.

We’ve built the system of record for post-sale workflows, powering onboarding and expansion for enterprise customers including Fortune 15 companies. Now we’re evolving that foundation into something much bigger: an intelligent system that actually does the work.

We’re building an agentic platform that eliminates friction in the B2B customer relationship.

The Role

We’re hiring a VP of Engineering to lead our transition into an AI-first company.

This is a hands-on leadership role. You will be deeply involved in architecture, product decisions, and execution. But the mandate is bigger:

Build and lead a new kind of engineering organization. You will own how this gets built, from architecture to team to execution.

A small, elite team powered by agents and AI, where:

• Engineering and Product operate in tight partnership to rapidly ship high-impact features
• Engineers achieve outsized leverage through modern tooling and automation
• Agents extend the team’s capacity and continue work asynchronously
• A lean team delivers at the impact of a much larger organization

What You’ll Own

1. Build an Agent-Driven Product

• Own the core product experience and technical direction of an AI-native platform used by enterprise customers
• Lead development of agent-based, AI-powered systems embedded in real customer workflows
   
• Build on a rich system of record with proprietary enterprise data
   
• Ship quickly while maintaining enterprise-grade reliability
   

2. Design the AI-Powered Engineering System

• Define how agents and tooling augment and accelerate engineering output
   
• Build infrastructure for AI-assisted product development at scale
   
• Continuously evolve how the team operates to maximize leverage and velocity
   

3. Elevate a High-Density Team

• Lead a small, high-caliber engineering team of 10 to 15
   
• Increase talent density, ownership, and execution standards
   
• Coach and develop engineers to thrive in an AI-augmented environment
   

4. Lead from the Front

• Stay close to architecture and critical technical decisions
   
• Engage directly in solving the hardest problems
   
• Set the pace for execution and quality
   

5. Drive Alignment and Impact

• Partner tightly with Product, Sales, and Customer Success
   
• Ensure what we build maps directly to customer value and revenue outcomes
   
• Communicate clearly across the organization and with customers when needed

Who You Are

A Builder Who Leads

• You have led engineering teams in early-stage, high-growth environments
   
• You have owned what gets built, shipped, and delivered to customers
   

Deeply Technical and Product-Oriented

• Strong track record building enterprise B2B products, ideally workflow-heavy or configurable systems
   
• High judgment on architecture, tradeoffs, and product quality
   

Building with AI

• Experience working with AI, machine learning systems, agents, or modern AI tooling
   
• You think about how AI changes both the product and how it gets built
   

Talent Builder

• Proven ability to attract, recruit, and develop strong engineers and teams
   
• You know how to create environments where high-performing teams thrive
   

Exceptional Communicator

• Clear, direct, and effective across engineers, executives, and customers
   
• Comfortable leading high-level technical and product conversations externally
   

Execution-Oriented

• You move quickly, prioritize effectively, and ship
   
• You focus on outcomes over process

What Makes This Role Unique

• Build on a real product with real enterprise customers, not a zero-to-one science project
• Leverage a strong data advantage through the workflows and systems we power
• Define a new model for engineering teams where AI meaningfully changes how software is developed
• Lead a small team designed for speed, ownership, and leverage
• Partner with an experienced leadership team across product, go-to-market, and operations
• Join a Boston-centered engineering culture with in-office collaboration that drives velocity (while remaining in-sync with remote members)

Requirements

• Experience leading engineering teams in startup or growth-stage environments
   
• Track record of building and scaling enterprise-grade B2B products
   
• Ability to operate across strategy, architecture, and execution
   
• Strong hiring instincts and ability to raise the bar on talent over time
   
• Based in Boston and eager to work in-office 3+ days a week

Why OnRamp

• Build a category-defining agentic platform for B2B
   
• Pioneer a new model of AI-powered product development
   
• Work with real enterprise customers solving real problems
   
• Join a company with strong momentum and recent Series A funding from top-tier investors
   
• High ownership, low bureaucracy, fast-moving team
   
• Competitive compensation and meaningful equity

Why OnRamp

• Work directly with enterprise and mid-market clients, including Fortune 15 companies
• Join a high-growth AI-first company that just raised its $15M Series A led by top investors
• Be part of a collaborative, ownership-driven culture
• Highly competitive cash compensation, equity, and benefits
• Boston-based, 3+ days a week in-office