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Head of SMB and Commercial Sales

Grammarly - United States - Hybrid

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Salary: USD 386,000 - 536,000 / annual

Superhuman (formerly Grammarly) is an AI productivity platform on a mission to unlock superhuman potential in everyone. The suite includes Grammarly's writing assistance, Superhuman Docs' collaborative workspaces, Mail's inbox management, and Go, a proactive AI assistant. The company serves over 40 million people, 50,000 organizations, and 3,000 educational institutions worldwide. As Head of SMB and Commercial Sales, you will lead the heritage Grammarly and Superhuman Go sales teams within the commercial business unit. You will own strategy, team development, and revenue performance for the Go sales motion across SMB and Mid-Market segments, operating as the senior sales leader and working within an ATU/STU (Account Team Unit/Segment Team Unit) model. Key responsibilities include: - Lead, coach, and develop a team of front-line managers and Account Executives to exceed revenue and activity targets - Own Go SMB and Commercial sales strategy and GTM execution, partnering with ATU leadership, Product, CS, and Marketing - Build team culture grounded in accountability, psychological safety, and continuous improvement - Drive rigorous pipeline management and forecasting discipline with visibility for senior leadership - Define and standardize onboarding, sales methodology, and enablement to reduce ramp time - Champion enablement by identifying skill gaps and ensuring the team has tools, training, and frameworks for complex, multi-value-prop deals - Serve as senior commercial presence on key deals, guiding strategy and supporting C-suite conversations - Partner cross-functionally with Product, Marketing, and CS to shape product narrative and influence roadmap - Represent the Go sales team in business unit leadership discussions - Hire, onboard, and retain exceptional talent The role offers a hybrid model with flexibility to work remotely, though you may be expected to travel for scheduled team collaboration weeks. Managers will determine in-person time based on business needs. QUALIFICATIONS: - 10+ years of SaaS sales experience, with at least 5 years in a sales leadership role managing Account Executives - Proven track record building and leading high-performing enterprise sales teams in land-and-expand or expansion-driven motions - Experience leading in matrixed or multi-product selling environments (STU/ATU, overlay, or specialist AE models) - Deep expertise in enterprise sales cycles with demonstrated success engaging VP and C-Suite stakeholders across IT, procurement, and multiple lines of business - Background in collaboration, productivity, or work management SaaS tools strongly preferred; experience at a progressive tech company with strong product culture is a plus - Strong coaching orientation—known for developing sellers and identifying skill gaps to build targeted development plans - Excellent command of recognized sales methodology (MEDDIC, MEDPICC, Challenger, or equivalent) and ability to embed into team practice - Skilled at building systems and processes in ambiguous environments; can design onboarding, enablement frameworks, and repeatable playbooks - Data-driven approach to pipeline management and team performance; Salesforce proficiency required - Exceptional cross-functional partnership skills with credibility and influence across Product, CS, Marketing, and executive stakeholders - Fluent in using AI tools in daily workflows and able to model and champion AI-enabled ways of working across the sales team - Demonstrated ability to work independently with minimal guidance, proactively manage tasks and priorities, analyze and execute work efficiently, and thrive in fast-paced, results-driven environments

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