Director of Sales - Pragmatic Institute : Job Details

Director of Sales (leadership)

We're seeking a Director of Sales who blends servant leadership with a coaching-first mindset—someone who knows what it takes to succeed as an individual contributor and is now driven to elevate others. This is an opportunity to join a high-growth, fast-paced startup where autonomy, adaptability, and leadership are key to success.

As Sales Manager, you will lead and develop a team of Account Executives across SMB, Mid-Market, and Enterprise segments, helping them consistently achieve (and exceed) quota. You'll bring firsthand knowledge of the sales trenches, combined with a deep investment in coaching, mentorship, and leadership. Your role is equal parts strategic leader and team builder, focused on driving revenue and growing a world-class sales team.

This is a role for a high-autonomy leader who thrives in ambiguous environments, loves rolling up their sleeves, and is passionate about creating scalable processes while supporting individual growth.

· Lead, mentor, and coach a team of AEs across diverse customer segments (SMB, Mid-Market, Enterprise).

· Drive quota attainment: Ensure the team consistently meets or exceeds revenue targets through proactive pipeline management and strategic sales execution.

· Invest in individual growth: Conduct regular coaching sessions, focusing on skill development, deal strategy, and career progression.

· Embody servant leadership: Remove obstacles for your team, create an environment where they can thrive, and lead by example.

· Refine sales processes: Identify opportunities for process improvement, implement best practices, and drive operational excellence within the team.

· Champion value selling: Coach AEs on leveraging the value selling framework, ensuring consultative, solution-oriented sales approaches that resonate with customer needs.

· Collaborate cross-functionally: Work closely with marketing, product, and customer success to align on messaging, feedback loops, and market insights.

· Report on performance: Provide accurate sales forecasts, performance updates, and pipeline health metrics to leadership.

· Foster a culture of accountability, continuous learning, and high performance within your team.

· 5-7 years of experience leading Account Executives, with a track record of driving teams to exceed targets.

· Prior success as an individual contributor (IC) in B2B SaaS sales, with a deep understanding of the sales cycle.

· Demonstrated quota attainment or overperformance as both an IC and leader.

· A true servant leader—you lead by empowering others, fostering trust, and creating an environment where your team can excel.

· Passionate about coaching and developing talent—you find fulfillment in helping others grow.

· Experience managing diverse segments: SMB, Mid-Market, and Enterprise accounts.

· Comfortable in a startup environment—you embrace change, operate autonomously, and thrive amid ambiguity.

· Familiar with value selling frameworks (e.g., Challenger, MEDDIC, SPIN) and able to coach AEs on these methodologies.

· Strong analytical and operational skills—comfortable with CRM tools (e.g., Salesforce, HubSpot) and data-driven decision-making.

· Exceptional communication and interpersonal skills, capable of influencing at all levels, including executives.

· Exposure to scaling sales teams in high-growth startups.

· Experience launching new territories, verticals, or go-to-market motions.

· Familiarity with sales enablement tools and sales automation platforms.

Pragmatic Institute is committed to enhancing the skills of our clients' key contributors and teams by providing practical, actionable training and hands-on learning experiences delivered by accomplished instructors and practitioners. Together, our three practices—product, design, and data—create a robust professional education program that enables us to help organizations transform key roles into powerful contributors and differentiators. Our client list reads like a who's who of today's biggest technology and Fortune 500 companies and our alumni rival Apple in their brand fanaticism and they all look to us to deliver the highest quality educational experiences.

We are a team of scrappy, driven collaborators working remotely all around the US who are dedicated to changing the face of professional education. We've made the Inc. 5000 fastest growing company list 9 times, and we've been named one of the best places to work in Arizona. We offer 13 PTO & 5 sick days (in addition to the week between Christmas and New Year's off). We take our work, but not ourselves, seriously and are looking for someone to join the team who is ready to make a real impact.