Senior Program Manager, International Sales Enablement

About this position

Rippling gives businesses one place to run HR, IT, and Finance. It brings together all of the workforce systems that are normally scattered across a company, like payroll, expenses, benefits, and computers. For the first time ever, you can manage and automate every part of the employee lifecycle in a single system.
Based in San Francisco, CA, Rippling has raised $1.4B+ from the world’s top investors—including Kleiner Perkins, Founders Fund, Sequoia, Greenoaks, and Bedrock—and was named one of America’s best startup employers by Forbes.
We prioritize candidate safety. Please be aware that all official communication will only be sent from @Rippling.com addresses.
About the role

Rippling is looking for a Sr. Program Manager, International Sales Enablement to join our Revenue Enablement team. You will have previous experience as an Account Executive, Sales Development Representative, Sales Manager, or Enablement Program Manager with a strong track record of executing strategic sales enablement initiatives. You’ll be partnered with the Head of Sales in our Toronto, Canada office—a growing, high‑investment hub where we are expanding our AE and SDR headcount. You’ll ensure members of this team have all the knowledge, skills, and process expertise they need to exceed their revenue goals. This will include optimizing new hire learning paths, architecting the ongoing enablement calendar, developing programs to drive better sales execution, facilitating training programs, assisting in product rollouts, and supporting broader international initiatives under SVP International Sales, Jameson Yung.
What you will do

Program Manage & Own Enablement Functional Expertise:

Develop and manage end‑to‑end sales enablement programs for AEs and SDRs in the Toronto region, including onboarding LPs, everboarding programs, sales documentation, and ongoing communications to ensure programs stick.
Execute and evaluate program effectiveness to ensure alignment with business objectives.
Become a domain expert in all things Toronto Sales to have a meaningful impact on strategic decision making.
Support broader international and global enablement initiatives under Jameson Yung as needed.
Communication & Stakeholder Management:

Partner with the Head of Sales (Toronto) and key stakeholders across Product Marketing, Revenue Operations, and Customer Experience to execute and evaluate program effectiveness.
Align stakeholders and collaborate with the broader Revenue Enablement team to execute strategies and manage cross‑functional initiatives.
Presentation / Facilitation Skills:

Facilitate sales skills training, including MEDDPICC, prospecting, negotiation, multi‑threading, and closing.
Coach AEs and SDRs on sales skills, processes, and new rollouts to ensure effective knowledge transfer.
Project Management:

Oversee multiple enablement projects, ensuring timely execution and alignment with strategic goals. Thrive in fast‑paced, highly ambiguous environments and get projects to completion.
Coordinate with cross‑functional teams to deliver on strategic initiatives, including those spanning the broader international business.
Analytical Skills:

Review and analyze data to inform enablement recommendations based on business gaps.
Interpret key performance metrics to identify opportunities for impact and ensure rapid AE and SDR ramp‑up and effectiveness.
Content Development:

Create and update onboarding content for new AEs and SDRs, ensuring relevance and accessibility.
Develop documentation and reference materials to support the Toronto sales team in quickly finding and adopting sales content.
What you will need

At least 5 years of relevant experience in Enablement, Program Management, Product Marketing, and/or Sales.
Ability to thrive in very fast‑paced environments, effectively managing shifting priorities and handling multiple tasks without becoming easily overwhelmed.
Strategic mindset with an ability to navigate ambiguity.
An aptitude for problem‑solving and working cross‑functionally with others.
Knowledge of MEDDPICC, sales skills training, and best practices for facilitating engaging sessions and conducting reinforcement.
Exceptional communication, presentation, and organizational skills.
Self‑starter with a bias toward action.
Strong operational excellence skills—understands how to organize chaos, streamline processes, and create workflows to support more efficient working processes.
Comfort working across international/global teams and an appreciation for regional nuance in sales contexts.
Qualifications

Undergraduate degree and/or equivalent work experience required.
At least 5 years of relevant experience in Enablement, Program Management, Product Marketing, and/or Sales.
AE, SDR, quota‑carrying, or enablement experience preferred.
In‑office 3 days per week in SF or Toronto preferred.
Additional Information

Rippling is an equal opportunity employer. We are committed to building a diverse and inclusive workforce and do not discriminate based on race, religion, color, national origin, ancestry, physical disability, mental disability, medical condition, genetic information, marital status, sex, gender, gender identity, gender expression, age, sexual orientation, veteran or military status, or any other legally protected characteristics. Rippling is committed to providing reasonable accommodations for candidates with disabilities who need assistance during the hiring process. To request a reasonable accommodation, please email accommodations@rippling.com.
Rippling highly values having employees working in‑office to foster a collaborative work environment and company culture. For office‑based employees (employees who live within a defined radius of a Rippling office), Rippling considers working in the office, at least three days a week under current policy, to be an essential function of the employee’s role.
This role will receive a competitive salary, benefits, and equity. The salary for US‑based employees will be aligned with one of the ranges below based on location.
The pay range for this role is:
USD 108,000 – 180,000 per year (US)
CAD 99,000 – 165,000 per year (CA)

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