Head of Retailer Onboarding

Location: HQ, Ithaca NY
Position: Full Time
Title: Head of Retailer Onboarding

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, omni-channel marketing and deep data services. IBM selected Rosie as the Top Startup in North America in its 2014 IBM Smartcamp Competition.

Job Summary
As Rosie’s Head of Onboarding your job will be to lead our world-class team of technical integration specialists and onboarding agents to help Rosie’s retailers get online and selling their products efficiently, effectively, and quickly. Your goal is to work to continually improve and enhance the onboarding process including: identification and advocacy of software solutions; development of our incredible Onboarding team’s professional knowledge and growth; relationship management of retailer and wholesaler clients through the onboarding part of their life cycle at Rosie; auditing resources and capacity planning; prioritization and management of the onboarding queue; and creating, measuring, and improving KPIs for the onboarding department.

Each new retailer with whom Rosie partners goes through an integration or “onboarding” process to launch online shopping. Rosie’s onboarding team guides retailers through this process and the team is responsible for completing many of the internal operational tasks that the process requires.

The primary objective of the team is to lead retailers through the entire onboarding process. This includes technical integration between their point of sale and Rosie’s eCommerce platform, project management of the multi-step onboarding process, training, written communication, documentation, and operational tasks.

This position is highly collaborative with other teams within the company. The Head of Rosie Onboarding works with the other team leads within Customer Success to ensure that Customer Success goals are reached. The Head of Onboarding also works with Rosie’s Tech Team to provide them with retailer feedback regarding our products. In addition, the Head of Onboarding makes sure all changes in software are actively communicated to the Onboarding Team and to Rosie’s end users moving through the onboarding process.


  • Actively engages and builds relationships with Rosie’s retailer partners to facilitate the onboarding process and better understand and improve the onboarding department.
  • Supports the adoption of the onboarding department’s vision, goals, and objectives at all levels as developed cooperatively with the Chief Customer Officer;
  • Leads the Onboarding team of onboarding professionals as they implement Rosie eCommerce with our retail clients;
  • Manages the onboarding funnel in the CRM including prioritization and unblocking blocked projects;
  • Dedicated to finding, using, and sharing data to make decisions and create processes that improve retailers’ experience with Rosie;
  • Uses tools to create dashboards and visualizations that track the full Onboarding team and individual KPIs of productivity and performance;
  • Create training processes and materials, from video to documentation, that brings new hires up to speed and grows existing team members;
  • Drives necessary changes for the improvement of operating and organizational efficiency of the onboarding team;
  • Work closely with Rosie’s Head of Support, Head of Account Management, and Head of Sales to unlock the value and potential of a single team with a focus of making retailers successful;
  • Assists the Chief Customer Officer in evangelizing the importance of retailer experience to the overall performance of the business;
  • Collects feedback from retailers and assists the Chief Customer Officer to influence the senior leadership team and stakeholders on proposed approaches and strategies for the department;
  • Develop documentation, training materials, and messaging for retailers and onboarding team;
  • Support department recruitment and training;
  • Mentor and develop the Onboarding team’s professional skills to foster continued internal growth
  • Clearly communicate a retailer’s onboarding status externally and internally;
  • Manage and advocate onboarding dependencies with Rosie’s Development Teams;
  • Turn our clients into ecommerce experts capable of independently operating a successful online storefront with Rosie software;
  • Plan and execute successful on-site retailer visits;
  • Understand and contribute to the Onboarding Team KPIs, Customer Success department strategic initiatives, and company goals;
  • Deliver a best in class experience: Retailers should be telling positive stories about Rosie to their industry peers, colleagues, friends and family to drive additional sales through references;
  • Develop, execute, and document novel Onboarding methodologies and technology for internal and external audiences.

Manager Responsibilities

  • Recruiting, interviewing and orienting new staff members;
  • Monitoring and evaluating staff performance;
  • Managing a departmental budget and forecasting budgetary requirements;
  • Setting strategic long and short-term departmental goals and evaluating outcomes;
  • Motivating and inspiring staff and facilitating personal growth;
  • Ensuring high levels of productivity are maintained;
  • Ensuring the highest levels of quality are met;
  • Communicating job expectations to staff;
  • Conducting training and seminars for continued skills improvement;
  • Fostering a productive working environment;
  • Ensuring adherence to company policies.



  • Bachelor’s Degree in operations management or related field, plus 5 years of relevant experience;
  • Associate’s Degree in operations management or related field, plus 8 years of relevant experience;
  • 5+ years experience managing high-performing individuals and teams
  • MBA advantageous;
  • Proven experience in management, operations, and leadership;
  • Understanding of business functions such as HR, Finance, marketing etc.;
  • Understanding of department finance and budgeting, including profit and loss, balance sheet and cash-flow management;
  • Demonstrable competency in strategic planning;
  • Working knowledge of data analysis and performance/operation metrics;
  • Working knowledge of IT/Business infrastructure and MS Office;
  • B2B experience;
  • Startup experience a plus (but not required);
  • Grocery experience a plus (but not required);
  • Software company experience a plus (but not required).


  • Outstanding organizational and leadership abilities;
  • Excellent interpersonal and public speaking skills;
  • Aptitude in decision-making and problem-solving;
  • Results driven;
  • Process driven;
  • Documentation obsessed;
  • Ability to diffuse situations;
  • Data analysis and KPI management;
  • Self-motivated and confident;
  • Highly organized and diligent;
  • Excellent written and verbal communication;
  • Ability to build consensus and relationships among managers, partners, and employees;
  • Solid project management skills with demonstrated experience managing multiple projects simultaneously;
  • Detail oriented, independent worker, flexible and interested in growing with the company;
  • Strong email and phone communication skills – concise, accurate, friendly;
  • Previous experience with JIRA, Confluence, Zoho, and Slack a plus (but not required).

Why Rosie

  • We provide the software and tools for you to succeed.
  • Our excellent team environment will nurture your talents.
  • We value results over experience and tenure.
  • We live to create moments that deliver delight.

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.

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