Senior Manager / Director of Learning and Development

San Francisco or Remote /
People /
Full Time
Before you read on, take a look around you. Chances are, pretty much everything you see has been shipped, often multiple times, in order to get there. E-commerce is exploding, and with it, parcel shipping is becoming a meaningful factor in a business' ability to succeed. Creating a compelling shipping experience for customers is hard but necessary.

At Shippo, our goal is to level the playing field by providing businesses access to shipping tools and terms that would not be available to them otherwise.

Shippo lowers the barriers to shipping for businesses around the world. As free and fast shipping becomes the norm, better access to shipping is a competitive advantage for businesses. Through Shippo, e-commerce businesses, marketplaces, and platforms are able to connect to multiple shipping carriers around the world from one API and dashboard. Businesses can get shipping rates, print labels, automate international documents, track shipments, and facilitate returns.

Internally, we think of Shippo as the building blocks of shipping. Shippos are a diverse set of individuals. We look for cultural and skill fit in every new person. Join us to build the foundations of something great, roll up your sleeves, and get important work done everyday. Founded in 2013, we are a proud team based out of San Francisco. Shippo’s investors include D1 Capital Partners, Bessemer Venture Partners, Union Square Ventures, Uncork Capital, VersionOne Ventures, FundersClub, and others.

About the Role

Shippo is looking for an experienced Senior Manager / Director of Learning and Development to join our growing team. This highly impactful role will design, implement, and scale all training and learning programs at Shippo. The ideal candidate has deep expertise in learning, facilitation, coaching, and program management. This hands-on role will work closely with department heads to identify opportunities to enhance organizational effectiveness, and provide systematic and straightforward approaches to training with measurable impact.


    • Design high-impact talent programs for manager capability and professional skills informed by business needs and industry research. Ability to design engaging programs for both in-person and virtual/distributed learning experiences.
    • Execute talent development programs end-to-end; create clear program project plans, stakeholder maps, and manage execution.
    • Work closely with the team to ensure programs embody our values.
    • Report on appropriate talent metrics; identify key insights to inform future actions and decision making. 
    • Deliver high impact training that maximizes learner participation, comprehension and application of the material utilizing technology, interaction, and innovative tactics.
    • Stay informed of talent trends, emerging learning technologies, and advanced thinking around solutions to accelerate talent and organizational effectiveness.


    • 7+ years working in program management with experience designing and scaling programs.
    • Proven experience in designing and implementing management effectiveness learning strategies, initiatives, and programs for people managers at all levels.
    • Experience building out effective use of Learning Management Systems.
    • A deep personal belief and commitment to diversity and belonging at work.
    • Strong project management skills, with exceptional stakeholder management and communication skills.
    • Experience facilitating learning through classes or workshops, both in person and remotely.
    • Detail-oriented, organized, and comfortable with technology. 
    • Comfort operating in a fast-paced start-up environment with the ability to successfully multitask and meet deadlines.
    • Bachelor’s degree in Organization Development, Psychology, Human Resources, Business or related experience.


    • Benefits: medical, dental, vision, (90% covered by the company, incl. dependents), and pets coverage
    • Flexible Time Off + work hours
    • 3 VTO days for ShippoCares volunteering events
    • $2,500 yearly learning stipend for your personal growth
    • Fun team events outside of work hours - happy hours, “escape room” adventures, hikes, and more!