VP, Head of Trailhead Product


May 1, 2021

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Job Category
Products and Technology
Job Details
Skill up for the future with Trailhead . The way the world works has completely changed and this demands new skills and new ways to learn. Help learners unlock their potential with personalized journeys tailored to their goals to learn new skills, earn valuable credentials, connect with our vibrant, modern community, and grow their companies and careers. We've also extended the magic of Trailhead to our customers with myTrailhead, the digital skilling platform to enable teams directly inside of Salesforce.
We’re looking for an amazing Head of Product that will lead the Trailhead and myTrailhead product teams into the future of innovative learning. You will lead our incredible team of product managers, own and define the holistic product strategy and vision, and work very closely and collaboratively with your counterparts in engineering and UX to build features and products that consistently delight our learners and customers.
If you thrive in a fast-paced, highly collaborative environment, live and breathe product (the process as much as the end result), love building and nurturing an amazing team, then this is the job for you!
Do you:

  • Believe that vision is just hope unless and until its paired with a sound & actionable strategy?

  • Think long term & strategic, but love delivering incremental value?

  • Read people and culture like tea leaves; building the relationships to make things happen?

  • Believe that focus is the most powerful (and underutilized) tool in our collective toolbelt?

  • Believe that shipping is a feature?

  • Start with the customer problem & experience and work backwards from there?

What our team is like:

  • We have a culture of ownership, delivery, and innovation

  • We believe that fun (and Keeping Trailhead Weird) and extraordinary technology are not mutually exclusive

  • We cultivate a hyper-transparent flow of information, conversation, and ideas

  • We are at the forefront of disrupting the entire learning industry


  • Define and own the product vision and strategy for Trailhead & myTrailhead

  • Driving the end to end product lifecycle for entire product suite. This includes: market needs, product vision and strategy, roadmap creation and communication, release planning, requirements gathering, functional specification all the way through to customer enablement and success.

  • Lead a team of 10+ product leaders guiding ~20 scrum teams

  • Work closely with the engineering, design & content teams to execute on the product vision and deliver a user experience that delights our users and meets their fundamental Jobs-To-Be-Done

  • Work with our marketing and sales teams to craft the right message, positioning and GTM strategy

  • Work directly with our customers & Trailblazers to validate and refine our product strategy and vision

  • Grow and nurture a team of amazing PMs while remembering that building a diverse and fulfilled team is as important as building the product

  • Communicate the long range and short term roadmap and vision to senior Salesforce executives, internal stakeholders & customers

  • Collaborate with, and influence product leaders in other clouds to enhance & amplify the Salesforce Customer 360 platform with digital skills and learning powered by Trailhead

Required Experience/Skills:

  • Prior experience in leading product teams and significant product portfolios that include revenue generating products

  • Ability to lead and define strategy autonomously

  • Ability to build and foster cross-functional and cross-org relationships to accomplish shared goals

  • Ability to present, communicate & get alignment with senior executives

  • Ability to handle multiple competing priorities & ambiguity in a dynamic environment

  • Familiarity with agile/scrum methodologies

Desired Skills:

  • Cloud computing experience is a strong plus

  • Working knowledge of Salesforce products

  • Experience with eLearning/education applications desirable

We are an equal opportunity employer and value diversity at our company. We do not discriminate on the basis of race, religion, color, national origin, gender, sexual orientation, age, marital status, veteran status, or disability status.
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