Job Type

Full-time

Description

The Director of Professional Learning leads a team dedicated to empowering educators and advancing Wayside’s mission through meaningful, instructionally grounded professional learning experiences. This role connects Wayside’s educational leadership and instructional integrity with the company’s strategic growth goals, ensuring that professional learning not only supports teachers’ success but also strengthens Wayside’s impact and sustainability.

The Director oversees the full lifecycle of Professional Learning: driving instructionally led sales enablement by partnering with Sales in pre-adoption opportunities, overseeing implementation and ongoing success for partner schools, and expanding Wayside’s reach through thought leadership and outreach to all educators. 

Who We Are

Wayside Publishing is a progressive developer of world language programs, resources, and materials for middle and high schools across the United States. We partner with educators to craft transformative texts and digital tools that engage students and foster successful communication and understanding across cultures.

Primary Responsibilities

Leadership and Team Development

• Lead, coach, and inspire the Professional Learning team to deliver exceptional educator-facing experiences grounded in pedagogy and purpose.
• Build a culture of collaboration, feedback, ownership, and growth aligned with Wayside’s mission and values.
• Support continuous professional growth for team members through coaching, modeling, and reflective feedback.
• Empower the team to see themselves as both educational leaders and strategic partners who contribute directly to company success.

Instructionally Led Sales Enablement

• Partner closely with Sales to deliver instructionally focused presentations and product demonstrations that help schools make informed, confident adoption decisions.
• ·Ensure Wayside’s educational credibility and mission are central to every sales interaction, modeling how we sell through education and integrity.
• Represent the educator’s perspective in RFPs, district presentations, and conferences to demonstrate real-world classroom impact.
• Collaborate with Sales and Marketing to shape authentic messaging and storytelling that communicate the instructional value of Wayside’s programs.

Post-Sales Implementation and Partner Success

• Oversee design and delivery of implementation trainings and ongoing PD that ensure teachers experience success, confidence, and joy using Wayside products.
• Evaluate program effectiveness through data and feedback, ensuring continuous improvement in delivery and impact.
• Build clear systems of communication between Professional Learning, Sales, and Customer Success to ensure a seamless teacher and district journey — from first contact to renewal.

Educator Engagement and Outreach

• Lead initiatives that extend Wayside’s support beyond current customers — offering meaningful PD for all world language teachers, regardless of product adoption.
• Position Wayside as a trusted educational thought leader through conference participation, webinar series, and partnerships in the language education community.
• Use outreach to nurture long-term relationships, build credibility, and strengthen Wayside’s visibility among districts and educators.
• Collaborate with Marketing to share success stories and insights that amplify Wayside’s presence and reinforce the company’s instructional mission.

Strategic Planning and Cross-Department Collaboration

• Develop a strategic vision for Professional Learning that aligns with company objectives, market opportunities, and educational best practices.
• Partner cross-functionally with Marketing and Sales leadership on: Go-to-market planning, product launch readiness, customer retention strategies, and messaging that connects instruction, impact, and business goals.                     
• Innovate new delivery models (in-person, virtual, asynchronous) that expand reach and accessibility.
• Use data and educator feedback to measure and communicate the dual impact of professional learning — on both instructional outcomes and organizational growth.

Other Duties as Assigned 

• Perform additional responsibilities as required to support the success of the program and the organization’s strategic goals.

Requirements

• Master’s degree in Education, Curriculum & Instruction, or related field.
• 10+ years of K–12 teaching and/or professional learning experience (world language preferred).
• 5+ years of leadership experience with proven success leading cross-functional collaboration.
• Strong record of developing and empowering high-performing teams.
• Deep understanding of adult learning, instructional coaching, and teacher engagement.
• Proven ability to balance instructional leadership with business strategy, connecting teacher outcomes to company success.
• Excellent communication and presentation skills across diverse educator and district audiences.
• Data-informed mindset; ability to demonstrate the measurable impact of professional learning initiatives.

What We Offer

• Competitive compensation: base salary plus achievement-based incentive program 
• Health insurance with options for dental, vision, life insurance, and more 
• Retirement savings plan with employer contribution 
• Employer-paid STD and LTD policies 
• Paid holidays 
• Work/life balance as a company value 

We believe that traditional hiring policies can hurt the most marginalized people in society, including people of color, people from working-class backgrounds, women, and LGBTQ people. Because we believe that these communities must be centered in the work we do, we strongly encourage applications from people with these identities or who are members of other marginalized communities.

Wayside Publishing is an Equal Opportunity Employer. All qualified applicants will receive consideration for employment without regard to race, color, religion, sex, sexual orientation, gender identity, or national origin.

No Phone Calls Or Recruiters Please

Salary Description

$130,000 – $145,000