VP of Engineering at Series A Startup

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.

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

• 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
  

• 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
  

• 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
  

• Stay close to architecture and critical technical decisions
  

• Engage directly in solving the hardest problems
  

• Set the pace for execution and quality
  

• 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

• You have led engineering teams in early-stage high-growth environments
  

• You have owned what gets built shipped and delivered to customers
  

• Strong track record building enterprise B2B products ideally workflow-heavy or configurable systems
  

• High judgment on architecture tradeoffs and product quality
  

• 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
  

• Proven ability to attract recruit and develop strong engineers and teams
  

• You know how to create environments where high-performing teams thrive
  

• Clear direct and effective across engineers executives and customers
  

• Comfortable leading high-level technical and product conversations externally
  

• You move quickly prioritize effectively and ship
  

• You focus on outcomes over process

• 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)

• 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

• 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

• 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.

What We Do

OnRamp helps companies win revenue by delivering value faster keeping customers engaged and reducing churn risk. With automation and AI-driven workflows OnRamp removes onboarding bottlenecks scales customer success teams and creates opportunities for retention and expansion from the start of every customer relationship.

Why Work With Us

OnRamp is a fast-growing Boston startup transforming how companies onboard and engage customers. We’re a team of builders and problem-solvers shaping the future of customer success with AI. Join us at an exciting inflection point to make an impact move fast and help redefine customer engagement.

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