Head of Onboarding, East

Vend Park•Boston, MA

6d•$135,000•Hybrid

About The Position

Vend Park is building the AI-powered operating system for parking in commercial real estate. The company has raised a $17.5M Series A from top investors. Vend Park replaces outdated, manual parking operations with a modern platform powered by automation, computer vision, and data, delivering 20%+ net operating income improvements for clients. In under two years, Vend Park has scaled to 20+ cities and partnered with leading asset owners. The company operates with high ownership, speed, and a bias toward action. This role is for an Onboarding Lead who will own the function that takes new properties from a signed deal to fully live, revenue-generating operations. This position sits at the center of Vend Park, bridging Sales, Operations, Product, and Customer Success. The Onboarding Lead will design systems that scale across dozens of concurrent launches while personally driving high-stakes implementations that require sharp judgment and strong client management. This is both a builder role (create systems) and an operator role (run live projects).

Requirements

Operator + Builder — You've run complex, multi-stakeholder projects end-to-end and you don't just execute — you design better systems.
High Judgment — You navigate ambiguity, tradeoffs, and client-specific edge cases. You know when to standardize vs. customize.
Exceptionally Organized — You manage multiple projects, timelines, and stakeholders without letting anything fall through the cracks.
Client-Facing & High EQ — You're comfortable pushing back, managing expectations, and building trust with difficult stakeholders.
Data-Driven — You're comfortable with messy data, pattern recognition, capacity forecasting, and process improvement.
Scrappy — You take initiative, operate like an owner, and thrive in fast-moving, sometimes ambiguous environments.
Enjoy Travel — This role requires travel up to 30% of the time.
4–8+ years of experience in operations, or client-facing roles, with a strong preference for backgrounds in finance (banking), consulting, or operations at high growth startups.
Demonstrated ability to manage complex onboarding engagements, lead multi-location rollouts, and build scalable processes from zero to one.

Nice To Haves

Experience in real estate, parking, or other physical operations environments is a plus, but not required.

Responsibilities

Own the full lifecycle from sales handoff through kickoff, configuration, go-live, and handoff to Account Management.
Manage multiple concurrent property launches across markets and ensure every onboarding is delivered on time, on budget, and with high client satisfaction.
Act as the central quarterback across Sales (handoff quality, expectation-setting), Product & Engineering (feature gaps, edge cases), and Operations (staffing, enforcement, on-site execution).
Define and enforce clear SLAs for every transition.
Build trusted relationships with property managers, asset managers, and key tenant stakeholders.
Lead onboarding calls, manage expectations, navigate pushback, and own escalations for complex or high-visibility clients.
Design onboarding playbooks, checklists, and workflows that scale across markets.
Identify bottlenecks — data collection, signage, tenant communications — and eliminate them.
Improve throughput and quality simultaneously.
Oversee setup of rates, passes, validations, billing structures, data uploads, system configuration, and third-party integrations (marketplaces, payments).
Ensure accuracy and completeness before every go-live.
Hire and manage onboarding coordinators as volume grows.
Delegate execution-heavy tasks while retaining ownership of outcomes and client experience.