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 OnRamp is proud to be an equal opportunity employer. We do not discriminate in hiring or any employment decision based on race, color, religion, national origin, age, sex (including pregnancy, childbirth, or related medical conditions), marital status, ancestry, physical or mental disability, genetic information, veteran status, gender identity or expression, sexual orientation, or other applicable legally protected characteristic. OnRamp considers qualified applicants with criminal histories, consistent with applicable federal, state and local law. OnRamp is also committed to providing reasonable accommodations for qualified individuals with disabilities and disabled veterans in our job application procedures. If you need assistance or an accommodation due to a disability, please don’t hesitate to let us know.

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