Sales Account Executive, Pressable

Automattic, the parent company of Pressable, is seeking an experienced Sales Account Executive to drive growth for their WordPress hosting services. This role involves managing the sales process from discovery to close, building strong customer relationships, and utilizing AI tools to enhance sales execution.

Responsibilities:

• Own the full sales process from initial customer engagement through close for mid-market and agency new business opportunities
• Build relationships with prospective customers and understand their business needs, technical requirements, and growth goals
• Conduct discovery calls, solution discussions, and presentations that clearly communicate the value of Pressable’s managed WordPress hosting platform
• Recommend the right products, packages, and terms to set customers up for long-term success
• Prepare proposals, pricing, and quotes that align with customer requirements and standard company guidelines
• Manage follow-up, pipeline progression, and next steps consistently across the sales cycle
• Drive new business through a mix of company-generated opportunities, outbound prospecting, and relationship-based selling
• Pull in technical or leadership partners when needed to support the deal and ensure customer confidence
• Handle commercial conversations confidently and partner internally on non-standard contract or custom-term negotiations as appropriate
• Support onboarding and maintain customer relationships that create opportunities for retention, upsell, and cross-sell
• Stay informed on market trends, competitive offerings, and customer pain points to improve effectiveness and win rates
• Own an individual revenue quota across new logo acquisition and strategic expansion within larger agency and mid-market segments
• Maintain disciplined pipeline management, forecasting, and deal documentation in HubSpot
• Ensure opportunities are properly qualified, structured, and progressed with clear next steps
• Identify expansion and long-term growth opportunities within high-value accounts
• Use AI tools to support account research, discovery preparation, deal analysis, and follow-up drafting
• Leverage call transcripts and AI-generated insights to identify objections, patterns, and next steps
• Apply judgment to AI outputs, knowing when to rely on automation and when human decision-making is required
• Collaborate with Solutions, Support, and Product teams to improve playbooks, pricing guidance, and feedback loops for strategic deals
• Contribute structured product and market feedback based on real customer conversations

Requirements:

• 3+ years of SaaS sales experience; experience in hosting, infrastructure, WordPress, or adjacent technology categories is strongly preferred
• Proven ability to manage opportunities through a full sales cycle and consistently hit or exceed targets
• Strong communication and presentation skills with the ability to engage both technical and non-technical buyers
• Consultative selling mindset with strong discovery, follow-up, and customer-facing problem-solving skills
• Technical curiosity and enough fluency to confidently discuss managed hosting and related customer requirements
• Strong organizational skills and a disciplined approach to pipeline management and execution
• Ability to collaborate effectively with internal partners across sales, marketing, support, and technical teams
• Results-driven, adaptable, and motivated by helping customers find the right solution. Strong judgment and prioritization skills in a fast-paced, evolving environment
• Proficiency with CRM systems (e.g., HubSpot), and disciplined pipeline management
• Comfort using AI-assisted sales tools to support research, preparation, follow-up, and deal analysis
• Experience selling to agencies, developers, or infrastructure-aware customers
• Experience working in sales environments that leverage AI for efficiency and insight