Return to site

Head of Customer Onboarding

Location: Ithaca preferred, but open to part-time telecommuting.

Position: Full-time


Company Overview

The industry leading online grocery shopping platform for mobile and web, Rosie launched in July 2013 and today enables customers to shop online from their favorite local stores for same day delivery or in­ store pickup. Rosie partners with leading local retailers and their wholesalers to provide e­-commerce, delivery opportunities, omni­channel marketing, and deep data services. The Tompkins County Chamber of Commerce recognized Rosie as the Distinguished Business of the Year in 2017 for its investment in downtown Ithaca, cultivating a modern workforce and being a pioneer in the Tompkins County tech service startup industry.

Job Summary

As the Head of Onboarding, your department's primary responsibility is to help grocery retailers efficiently launch their online service with ease. The team of onboarding specialists you lead are the first team members in Rosie Customer Success to work with retailers. They must nurture and grow the relationship with retailers built on trust and communication.

The time it takes to get a signed store live is a key differentiator in the grocery eCommerce marketplace. It is your responsibility to manage the daily activities of the onboarding team while recommending further courses of action to scale the onboarding segment of the organization. As part of the Rosie Management team, build an onboarding process that allows the team to plan effectively and understand the progress of launches across many simultaneous projects. High quality implementations delivered on-time are essential to your success.

The Onboarding department has direct integration with Rosie’s other Customer Success teams including retailer marketing, account management, and support. You will interface regularly with senior leadership team members. Additionally, as Head of Onboarding, you will represent the needs of retailers and the Onboarding department with a variety of departments including: Sales, Marketing, Product, Development, and Support.

The Head of Onboarding reports directly to the Chief Customer Officer (CCO).

General Responsibilities

  • Develop with the CCO the goals for the onboarding department;

  • Work with the CCO to define and implement action plans required to achieve the department goals;

  • Manage the Onboarding team members establishing performance and quality standards, providing developmental feedback, performance evaluations, approval of expense reports, etc.

  • Act as an escalation point in difficult situations regarding customer issues and provides leadership and optimal service in such situations

  • Provide onboarding status information to internal customers and external customers;

  • Interface with outside technology providers related to onboarding stores (primarily POS systems and POS providers);

  • Deliver a world class experience: Retailers should be telling positive stories about Rosie to their friends and family;

  • Develop, execute, and report on business plan revenue and other KPIs;

  • Develop department annual budget submission for revenue and expense;

  • Own Rosie Help Center documentation for onboarding; and

  • Manage the expenses of the department and reach a 50% margin;

General Management

  • Recruits, hires, disciplines, and recommends separations of Onboarding staff members as required to maintain a skilled, enthusiastic, and productive workforce;

  • Provides leadership and conduct performance reviews of direct reports;

  • Coaches and develops Onboarding staff members on issues relating to working with others. company policy, and good decision-making skills;

  • Identify areas for cost reductions and operational improvements; and

  • Prepare informational analysis on current processes, actual performance versus plan and prior year data.

Job Requirements

Results-oriented operations leader with extensive experience in project management and operations as a project lead. Proven ability to achieve results under pressure and challenges in fast-paced startup company environment.


  • Bachelor's degree or related field required;

  • Minimum three (3) years of supervisory or lead experience over a team;

  • Minimum of two (2) years of experience of project management skills with demonstrated experience managing multiple projects simultaneously.

  • Preferred - prior experience in software implementation or other related operations. Experience with project management tools a plus.


  • Strong knowledge of Microsoft Office Suite, especially MS Word and Excel.

  • Proven ability to build effective relationships and influence the decision-making process.

  • Excellent verbal and written communication skills;

  • Strong time management, decision-making, and organization skills;

  • Self-starter with strong strategic thinking skills;

  • Demonstrates ability to consistently pull a wide variety of data into a well-constructed and supportable analysis;

  • Ability to multitask and meet deadlines required;

  • Strong leadership and interpersonal skills and ability to work with a diverse group of people successfully;

  • Detail oriented, independent worker, flexible, open to learning and growing with the company.

  • Proficient in training others and facilitating training activities.

  • Self-directed with ability to meet deadlines and quality expectations.

  • Strong customer service skills and experience.

  • Strong knowledge of project management tools, principles, budgeting, and team management.

Why Rosie:

  • We provide the software and tools for you to succeed.

  • Our excellent team environment will bring out the best of your talents and help your career.

  • We value results over experience and tenure.

  • We live to create moments that deliver delight.

To Apply:

Send resume and cover letter to

Rosie is an Equal Opportunity/Affirmative Action Employer. All qualified applicants will receive consideration for employment without regard to race, color, religion, sex, pregnancy, sexual orientation, gender identity, national origin, age, protected veteran status, or disability status.

All Posts

Almost done…

We just sent you an email. Please click the link in the email to confirm your subscription!

OKSubscriptions powered by Strikingly