Head of Sales

Boston, MA

Hybrid Office, 3 days onsite

About Us 

Stride Funding is a venture-backed, mission-driven startup transforming access to education and career pathways. We are revolutionizing the way employers attract and retain critical talent, while simultaneously tackling the student debt crisis. (Yep, we think BIG.) Our innovative platform meaningfully connects employers, educational institutions, and diverse talent to drive mutual benefit—using accessible education financing as the thread. We like to think of ourselves as more than a fintech; we’re a catalyst for economic mobility. 

A Forbes Fintech 50 company, portfolio company of SHRM (Society of Human Resource Management — the largest HR organization out there!) and recipient of “Startup of the Year” by StartUp Boston, Stride is driven by our commitment to social impact and innovation. We are reshaping the future of the workforce one opportunity at a time. Join us on our journey to give power to learners and unlock fulfilling careers that drive positive change in their communities and beyond.

What We Need

Stride is excited to bring on a dynamic and experienced Head of Sales to lead our sales team. As a key member of our leadership team, you will play a pivotal role in driving revenue growth by developing and executing effective sales strategies targeting Chief Human Resources Officers (CHROs) and other People Leaders at the enterprise level. The ideal candidate will have a proven track record of success in sales leadership roles, particularly in selling to CHROs, and will bring a strategic mindset, strong leadership skills, and a passion for building high-performing sales teams.

What You'll Do

• Lead and develop our brand new sales team, providing guidance, mentorship, and support to help team members achieve their goals and objectives.
• Develop and implement strategic sales plans to achieve revenue targets and expand our customer base within the enterprise segment.
• Collaborate with our Partnerships and Operations teams to identify opportunities for cross-functional collaboration and develop solutions that meet the needs of our customers.
• Build and refine sales processes and methodologies to drive efficiency and effectiveness across the sales organization.
• Monitor and analyze sales performance metrics, identify areas for improvement, and implement initiatives to continuously optimize sales performance.
• Stay informed about industry trends, market dynamics, and competitor activities to inform sales strategies and tactics.
• Cultivate strong relationships with key stakeholders, including CHROs and other senior executives, to drive business development and partnership opportunities.
• Develop and maintain relationships with our key Channel partners 
• Represent Stride at industry events, conferences, and networking opportunities to promote our brand and generate leads.

What You'll Need

• 5+ years of experience in sales leadership roles, with a track record of success in driving revenue growth and leading high-performing sales teams.
• Proven experience selling to CHROs and other senior executives at the enterprise level, preferably in the healthcare industry.
• Strong strategic thinking and analytical skills, with the ability to develop and execute complex sales strategies.
• Excellent leadership and management skills, with the ability to inspire and motivate a diverse team of sales professionals.
• Demonstrated ability to build and maintain strong relationships with customers, partners, and internal stakeholders.
• Excellent communication and presentation skills, with the ability to effectively articulate value propositions and influence decision-makers.
• Bachelor's degree in Business Administration, Sales, Marketing, or a related field; MBA or relevant advanced degree is a plus.
• Strong experience utilizing CRM software and sales engagement tools 
• Role may require up to 25% travel

What We Give in Return

• Competitive cash and equity compensation 
• Attractive incentive compensation structure
• Health benefits (health & dental), 401k
• Commuter benefits
• Flexible PTO policy
• Opportunities to grow and perform in a fast-paced environment alongside a stellar team

If you are a highly driven individual with a passion for sales and technology, and you thrive in a dynamic and fast-paced environment, we want to hear from you! Join us in revolutionizing the workforce solution industry and making a meaningful impact on businesses worldwide. Apply now to be a part of our growing team!

We are committed to creating a diverse and inclusive workplace where all employees feel valued, respected, and empowered to contribute their unique perspectives and talents. Stride is an equal opportunity employer and prohibits discrimination and harassment of any kind. We embrace diversity and are dedicated to providing equal employment opportunities to all individuals regardless of race, color, religion, sex, sexual orientation, gender identity, national origin, age, disability, veteran status, or any other characteristic protected by law.