Head of Sales, Americas

About Glean:

Founded in 2019, Glean is an innovative AI-powered knowledge management platform designed to help organizations quickly find, organize, and share information across their teams. By integrating seamlessly with tools like Google Drive, Slack, and Microsoft Teams, Glean ensures employees can access the right knowledge at the right time, boosting productivity and collaboration. The company’s cutting-edge AI technology simplifies knowledge discovery, making it faster and more efficient for teams to leverage their collective intelligence.

Glean was born from Founder & CEO Arvind Jain’s deep understanding of the challenges employees face in finding and understanding information at work. Seeing firsthand how fragmented knowledge and sprawling SaaS tools made it difficult to stay productive, he set out to build a better way - an AI-powered enterprise search platform that helps people quickly and intuitively access the information they need. Since then, Glean has evolved into the leading Work AI platform, combining enterprise-grade search, an AI assistant, and powerful application- and agent-building capabilities to fundamentally redefine how employees work.

About the Role:

As the Head of America Sales for Glean, you will lead all of sales management and their account executive (AE) teams across the U.S., setting the strategic direction for sales while ensuring operational excellence. Your mission is to drive substantial bookings growth, scale high-performing teams, and establish a best-in-class sales culture that positions us as a leader in the AI SaaS market.

You will:

• Lead and Inspire Teams: Manage and motivate a team of front-line Sales Managers and AEs, setting ambitious bookings targets and driving consistent over-achievement.
• Execute Strategic Growth Plans: Partner with global go-to-market (GTM) leadership to implement region-specific strategies, processes, and systems tailored to enterprise clients, focusing on verticals like technology, finance, and manufacturing.
• Optimize Sales Processes: Instill repeatable sales methodologies and training programs to boost rep productivity, addressing the complexity of AI solution sales with usage-based pricing.
• Define and Track KPIs: Develop and manage Americas-Specific sales KPIs (e.g., bookings per rep, win rates, Global 2000 penetration), dashboards, and forecasting in Salesforce for transparency and growth tracking.
• Collaborate Cross-Functionally: Work closely with Marketing, Product, and Enablement teams to refine GTM motions, ensuring alignment with the market dynamics and AI product innovations.
• Foster Inclusive Culture: Model and reinforce a sales culture of respect, integrity, inclusion, and transparency, championing diversity, equity, and inclusion (DEI) initiatives across diverse markets.
• Drive Operational Excellence: Identify opportunities to streamline systems, coach managers, and scale operations, reducing sales cycle friction.
• Ensure Pipeline and Deal Quality: Implement best practices for pipeline generation, customer engagement, and deal execution, targeting 30% of bookings from Global 2000 clients.
• Build Leadership Bench: Hire, mentor, and retain top sales talent, strengthening leadership and AE capabilities through targeted development programs.
• Act as a Role Model: Exemplify ethical, skillful, and data-driven leadership, raising the bar for sales excellence across

About you:

• 10+ years of experience as a front-line enterprise sales manager in SaaS or technology, with additional experience managing managers in multi-team leadership roles.
• Proven ability to lead and scale high-performing sales organizations, ideally in enterprise AI or SaaS.
• Demonstrated success in meeting or exceeding bookings targets, with a focus on enterprise segments (e.g., $1M+ ACV deals).
• Track record of hiring, coaching, and developing sales leaders and AEs 
• Fluency in Salesforce and modern sales tech stacks (e.g., Clari, Gong), with data-driven decision-making skills.
• Exceptional communication, collaboration, and cross-functional leadership
• Experience fostering inclusive team cultures and championing DEI initiatives.

Preferred qualifications:

• Second-line leadership experience (managing managers) in enterprise AI or SaaS at a high-growth company.
• Deep understanding of enterprise markets, including verticals like technology, finance, or electronics, with a track record of Global 2000 wins.
• Strong business acumen, analytical skills, and executive presence for engaging C-level stakeholders.
• Passion for building scalable systems, experimenting with AI-driven sales tools, and driving continuous improvement.

Location: 

• This role is remote and based in a major U.S. Hub
• Requires up to 50% travel across to meet clients, attend industry events, and visit regional offices.

Compensation & Benefits:

Compensation offered will be determined by factors such as location, level, job-related knowledge, skills, and experience. Certain roles may be eligible for variable compensation, equity, and benefits.

We offer a comprehensive benefits package including competitive compensation, Medical, Vision, and Dental coverage, generous time-off policy, and the opportunity to contribute to your 401k plan to support your long-term goals. When you join, you'll receive a home office improvement stipend, as well as an annual education and wellness stipends to support your growth and wellbeing. We foster a vibrant company culture through regular events, and provide healthy lunches daily to keep you fueled and focused.

We are a diverse bunch of people and we want to continue to attract and retain a diverse range of people into our organization. We're committed to an inclusive and diverse company. We do not discriminate based on gender, ethnicity, sexual orientation, religion, civil or family status, age, disability, or race.