VP, Trailhead Product

Airkit

Airkit

Product
San Francisco, CA, USA
Posted on Mar 5, 2026

Description

Job Details:

We are looking for a thoughtful, talented, and experienced Vice President of Product to lead Trailhead's product strategy and vision. Trailhead is Salesforce's premier learning platform that has empowered millions of learners worldwide to develop skills, earn credentials, and advance their careers. Do you spend your time thinking about the future of learning and skills development? Are you fascinated by how AI and personalization are transforming education? Do you love driving product strategies that move markets and change lives? If so, then this role is for you.

About Trailhead:

Trailhead is more than a learning platform – it's a global movement. We're building the future of learning for the Salesforce ecosystem and beyond, helping learners, employers, and partners succeed in the digital economy. In this role, you'll have the opportunity to shape how millions of people learn, grow, and connect to career opportunities.

Your Responsibilities Will Include:

Product Vision & Strategy

  • Creating and delivering a compelling multi-year product vision and strategy for Trailhead that aligns with Salesforce's broader business objectives

  • Defining and prioritizing the product roadmap based on learner needs, market trends, and business impact

  • Identifying opportunities to leverage AI, personalization, and skills-based hiring trends to transform the learning experience

  • Positioning Trailhead competitively in the learning and skills development marketplace

Leadership & Team Development

  • Building, mentoring, and leading a high-performing global product management team

  • Creating an inclusive culture that values diversity, collaboration, and innovation

  • Developing talent and creating clear career growth paths for team members

  • Driving organizational alignment across product, engineering, design, content, and marketing teams

Cross-Functional Partnership

  • Partnering closely with Content, Marketing, Engineering, Design, and Customer Success teams to deliver world-class learning experiences

  • Working with field teams and customer-facing organizations to ensure Trailhead drives measurable business value

  • Collaborating with senior leadership across Salesforce to align Trailhead's strategy with company priorities

  • Building strong relationships with partners and the broader Salesforce ecosystem

Operational Excellence

  • Establishing clear product development processes and methodologies that balance speed with quality

  • Defining and tracking success metrics and KPIs that demonstrate business impact

  • Making data-driven decisions based on analytics, user research, and market insights

  • Managing resource allocation and capacity planning across the product portfolio

Customer & Market Focus

  • Maintaining deep empathy for learners, employers, and the Salesforce ecosystem

  • Conducting user research and validation to ensure products meet real needs

  • Engaging with customers and stakeholders to gather feedback and build relationships

  • Staying current on EdTech trends, competitive landscape, and market opportunities

Position Requirements:

Must-Have Qualifications:

  • 10+ years of product management experience, with 5+ years in leadership roles

  • Proven track record of building and launching successful products at scale

  • Experience leading global, cross-functional teams in complex, matrixed organizations

  • Strong technical acumen with ability to partner effectively with engineering teams

  • Demonstrated ability to develop and execute multi-year product strategies

  • Excellence in stakeholder management and executive communication

  • Bachelor's degree required; MBA or advanced degree preferred

Leadership Competencies:

  • Inspiring leadership style with focus on developing and empowering teams

  • Commitment to building diverse, inclusive, and high-performing organizations

  • Ability to influence without authority and build consensus across teams

  • Track record of attracting, retaining, and developing top talent

  • Strong decision-making skills with comfort navigating ambiguity

Product Excellence:

  • Deep understanding of product development methodologies (Agile, Lean, etc.)

  • Data-driven approach to product decisions with strong analytical skills

  • Experience with consumer and/or enterprise products with millions of users

  • Understanding of platform architecture and scalability considerations

  • Ability to balance technical excellence with time-to-market

Domain Knowledge (Desired):

  • Experience in learning platforms, EdTech, or skills development

  • Understanding of B2B and B2C product dynamics

  • Knowledge of AI, personalization, and recommendation systems

  • Familiarity with credentialing, certification, and workforce development

  • Experience with community-driven or ecosystem products

What Makes This Role Unique:

  • Impact at Scale: Trailhead reaches millions of learners globally—your decisions will directly impact careers and lives

  • Innovation Opportunity: Shape the future of learning with AI, personalization, and skills-based technologies

  • Ecosystem Connection: Work at the intersection of learning, technology, and the Salesforce ecosystem

  • Executive Visibility: Present regularly to senior leadership and influence company-wide strategy

  • Mission-Driven: Help democratize learning and create equal opportunities for all

Success Metrics:

Within your first year, you will:

  • Develop and communicate a clear 3-year product vision for Trailhead

  • Build strong relationships with key stakeholders across the organization

  • Establish a high-performing product organization with clear roles and responsibilities

  • Launch at least one major product initiative that drives measurable learner and business impact

  • Create a data-driven framework for measuring product success and ROI

For roles in San Francisco and Los Angeles: Pursuant to the San Francisco Fair Chance Ordinance and the Los Angeles Fair Chance Initiative for Hiring, Salesforce will consider for employment qualified applicants with arrest and conviction records.