Senior Sales Account Executive, Pressable

Automattic is the parent company of Pressable, a premier managed WordPress hosting provider. They are seeking a Senior Sales Account Executive to drive growth across larger agency and mid-market customers, managing complex sales opportunities and building strategic relationships.

Responsibilities:

• Own and manage larger, more complex agency and mid-market opportunities from discovery through close
• Build and manage relationships with both technical contacts and executive or business decision-makers
• Position Pressable’s platform as a long-term strategic partner for agencies and mid-market customers
• Lead deep technical and business discovery to understand customer goals, constraints, and success criteria
• Lead sophisticated opportunities involving multiple stakeholders, technical requirements, custom commercial structures, and non-standard deal terms
• Act as the quarterback across the deal cycle, coordinating technical experts and internal partners to move opportunities forward efficiently
• Deliver compelling presentations, solution walkthroughs, and business conversations tailored to the customer’s needs
• Develop proposals, pricing recommendations, and commercial packages that align customer requirements with company goals
• Lead contract and negotiation strategy in partnership with leadership, balancing creativity, customer value, and sound business judgment
• Maintain comprehensive market awareness, including customer needs, competitive dynamics, and industry trends, and use those insights to strengthen deal strategy
• Lead competitive positioning against alternative hosting platforms and infrastructure solutions, clearly articulating Pressable’s differentiation in performance, support, and partnership
• Support successful onboarding and identify expansion opportunities by maintaining strong post-sale relationships with customers
• Contribute to new business development through a mix of pipeline conversion, relationship-building, and proactive opportunity creation
• Proactively build and execute strategic outbound plans into high-value target accounts, including named account mapping and executive-level outreach
• 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:

• 6+ years of SaaS sales experience, including selling hosting-related solutions; managed hosting or WordPress hosting experience strongly preferred
• Demonstrated success selling sophisticated, high-value solutions with longer or more consultative deal cycles
• Experience selling to agencies, mid-market customers, or technical buyers
• Strong discovery, consultative selling, and negotiation skills
• Strong business acumen with the ability to connect customer needs to commercial outcomes
• Excellent communication skills across both technical and non-technical audiences
• Strong technical fluency, comfort, and credibility discussing WordPress, hosting, infrastructure, and platform-related concepts
• Proven ability to negotiate creatively, manage complexity, and solve problems in a way that creates value for both the customer and the business
• Strategic mindset with the ability to shape deal strategy, prioritize effectively, and operate with a high level of autonomy
• Collaborative working style and a track record of partnering well across sales, marketing, product, support, and technical teams
• Adaptability, sound judgment, and a proactive, results-oriented approach
• Ability to manage multi-stakeholder conversations and non-linear deal processes
• Comfort translating technical platform capabilities into clear business value
• 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 hosting-related solutions; managed hosting or WordPress hosting strongly preferred
• Experience selling to agencies, developers, or infrastructure-aware customers
• Experience working in sales environments that leverage AI for efficiency and insight