Account Executive, Automattic

• 4+ years of B2B quota-carrying experience in Ecommerce, SaaS, or platform sales, with consistent attainment against multi-hundred-thousand or seven-figure annual targets
• Proven success selling to Midmarket or Enterprise clients with complex buying groups, procurement, security, and legal reviews
• Demonstrated outbound prospecting skills, including account research, sequencing, and executive-level outreach that converts to qualified opportunities
• Strong command of consultative and value-based selling, including discovery, economic impact modeling, and business case development
• Experience running structured deal processes with multi-threading, mutual action plans, and disciplined pipeline management
• Strong understanding of enterprise software, IT landscapes, and content management systems
• Comfortable working with executive-level prospects, negotiating terms, and reviewing contracts
• Comfortable in a high-growth, builder environment. You can operate with imperfect data, roll up your sleeves, and still deliver clean execution
• Excellent communication and presentation skills, written and verbal, with the ability to simplify technical concepts for non-technical stakeholders
• High integrity, ownership, and a team mindset. You share wins, ask for help early, and put the merchant outcome first
• Self-motivated with a drive to achieve revenue and growth targets, both individually and as part of the company

Desirable

• We’re looking for an experienced Midmarket Account Executive to join our Sales team
• This role is critical to building on our momentum with our high value merchants ($1M+ TPV) as well as shaping how we leverage the strengths of our full organization to drive more wins in the field
• If you are a top performer, this is a chance to plug into a product with real market pull and help build and scale a modern sales-led growth motion alongside it
• You will work complex deals, win marquee logos, and create expansion playbooks that others will follow. Bring your craft, your curiosity, and your conviction
• We will back you with a platform merchants love, a team that plays to win, and the tools to make it happen
• Own a revenue target for net-new acquisition and expansion across Midmarket and Enterprise merchants with $1M+ TPV
• Successfully manage both transactional deals and larger, more complex opportunities that involve partner products and agency services
• Team-sell with a partner Sales Engineer to co-sell complex solutions, lead discovery, shape requirements, and build compelling value cases that tie to merchant outcomes
• Run the full sales cycle from prospecting to close: discovery, solution mapping, business case, negotiation, and executive alignment
• Build urgency and clear close plans with verifiable next steps, stakeholder maps, and documented mutual action plans
• Maintain accurate sales forecasts and pipeline information, and drive strategic improvement of forecasting processes
• Land and expand. Drive initial wins, then grow accounts through cross-sell and upsell across platform, payments, and partner solutions
• Actively engage in pipeline generation activities, including regular outbound prospecting and partner agency relationship management
• Represent the brand at events, webinars, and partner activities, developing a healthy referral and partner-sourced pipeline
• Collaborate cross-functionally with Product, Marketing, Agency and Technical Partnerships, Customer Success, and Support to remove friction and accelerate time to value
• Translate market feedback into crisp insights for product and leadership, including competitive signals and gaps that block adoption
• Develop and execute innovative, vertical-specific sales strategies that accelerate market penetration
• Contribute to a high-performing sales culture by sharing best practices and mentoring team members. Help refine playbooks, messaging, and tooling as we scale a modern SLG motion alongside our PLG engine