Grammarly

Head of Sales

Grammarly

full-time

Posted on:

Location Type: Remote

Location: United States

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Salary

💰 $318,000 - $460,000 per year

Job Level

Lead

About the role

  • Lead, coach, and develop a team of Coda AEs to consistently exceed revenue and activity targets across all segments
  • Own the Coda sales strategy and GTM execution, partnering with ATU leadership, Product, CS, and Marketing to drive a cohesive, high-performance sales motion
  • Build and maintain a team culture grounded in accountability, psychological safety, and continuous improvement — where sellers feel supported, and their work has clear impact
  • Drive rigorous pipeline management and forecasting discipline, maintaining accuracy and visibility for senior leadership
  • Define and standardize onboarding, sales methodology, and enablement for the Coda AE team to reduce ramp time and improve consistency
  • Champion enablement: identify skill gaps, partner with the enablement function, and ensure the team has the tools, training, and frameworks to run complex, multi-value-prop deals
  • Serve as the senior commercial presence on key deals — guiding team strategy, supporting C-suite conversations, and helping navigate late-stage complexity
  • Partner cross-functionally with Coda Product, Marketing, and CS leadership to shape the product narrative, surface customer insights, and influence roadmap priorities
  • Represent the Coda sales team in BU leadership discussions, providing a grounded sales perspective on go-to-market decisions
  • Hire, onboard, and retain exceptional Coda AE talent, building a bench ahead of growth and planned leave coverage

Requirements

  • 7–12 years of SaaS sales experience, with at least 3–5 years in a sales leadership role managing a team of Account Executives
  • Proven track record of building and leading high-performing enterprise sales teams in a land-and-expand or expansion-driven motion
  • Experience leading in a matrixed or multi-product selling environment (e.g., STU/ATU, overlay, or specialist AE model) — comfortable driving results without direct control of all inputs
  • 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 a strong product culture is a plus
  • Strong coaching orientation — known for developing sellers, not just managing pipeline; can identify skill gaps and build targeted development plans
  • Excellent command of a recognized sales methodology (e.g., MEDDIC, MEDPICC, Challenger, or equivalent) and ability to embed it 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 — able to align with Product, CS, Marketing, and executive stakeholders with credibility and influence
  • Fluent in using AI tools in daily workflows and able to model and champion AI-enabled ways of working across the sales team.
  • Has a demonstrated ability to work independently with minimal guidance, proactively manages tasks and priorities across multiple projects, analyzes and executes work efficiently, collaborates effectively with cross-functional teams, and thrives in fast-paced, results-driven environments.
Benefits
  • Excellent health care (including a wide range of medical, dental, vision, mental health, and fertility benefits)
  • Disability and life insurance options
  • 401(k) and RRSP matching
  • Paid parental leave
  • 20 days of paid time off per year, 12 days of paid holidays per year, two floating holidays per year, and flexible sick time
  • Generous stipends (including those for caregiving, pet care, wellness, your home office, and more)
  • Annual professional development budget and opportunities
Applicant Tracking System Keywords

Tip: use these terms in your resume and cover letter to boost ATS matches.

Hard Skills & Tools
SaaS salessales leadershipenterprise sales cyclessales methodologypipeline managementonboarding frameworksenablement frameworksdata-driven decision makingAI toolsSalesforce
Soft Skills
coaching orientationcross-functional partnershipindependent worktask managementcollaborationadaptabilityaccountabilitypsychological safetycontinuous improvementinfluence