Senior Sales Account Executive, Pressable

About this role

<p><a href="https://pressable.com/">Pressable</a> (“WordPress hosting that means business”) seeks an experienced, motivated, and empathetic professional with the expertise to help us meet or exceed aggressive growth goals for our superb WordPress hosting company.</p> <p>Pressable is seeking an experienced, strategic, and consultative Sales Account Executive (SAE) to help drive growth across larger agency and mid-market customers. You’ll own complex sales opportunities end-to-end, from deep discovery through negotiation and close, and serve as a trusted advisor to customers with sophisticated performance, scale, and workflow requirements.</p> <p>This is a senior individual contributor role designed for someone who thrives in longer sales cycles, multi-stakeholder environments, and consultative selling motions. The SAE role is intentionally structured to leverage AI as a force multiplier for research, preparation, and insight, while keeping human judgment, relationship-building, and decision-making at the center of the sales process.</p> <p>You will report to the Head of Sales & Enablement and work closely with Solutions, Support, and Product partners to ensure high-quality execution across strategic opportunities.</p> <h4>Responsibilities</h4> <p>Strategic Deal Ownership</p> <ul> <li>Own and manage larger, more complex agency and mid-market opportunities from discovery through close.</li> <li>Build and manage relationships with both technical contacts and executive or business decision-makers.</li> <li>Position Pressable’s platform as a long-term strategic partner for agencies and mid-market customers.</li> <li>Lead deep technical and business discovery to understand customer goals, constraints, and success criteria.</li> <li>Lead sophisticated opportunities involving multiple stakeholders, technical requirements, custom commercial structures, and non-standard deal terms.</li> <li>Act as the quarterback across the deal cycle, coordinating technical experts and internal partners to move opportunities forward efficiently.</li> <li>Deliver compelling presentations, solution walkthroughs, and business conversations tailored to the customer’s needs.</li> <li>Develop proposals, pricing recommendations, and commercial packages that align customer requirements with company goals.</li> <li>Lead contract and negotiation strategy in partnership with leadership, balancing creativity, customer value, and sound business judgment.</li> <li>Maintain comprehensive market awareness, including customer needs, competitive dynamics, and industry trends, and use those insights to strengthen deal strategy.</li> <li>Lead competitive positioning against alternative hosting platforms and infrastructure solutions, clearly articulating Pressable’s differentiation in performance, support, and partnership.</li> <li>Support successful onboarding and identify expansion opportunities by maintaining strong post-sale relationships with customers.</li> <li>Contribute to new business development through a mix of pipeline conversion, relationship-building, and proactive opportunity creation.</li> <li>Proactively build and execute strategic outbound plans into high-value target accounts, including named account mapping and executive-level outreach.</li> <li>Own an individual revenue quota across new logo acquisition and strategic expansion within larger agency and mid-market segments.</li> </ul> <p>Pipeline & Account Management</p> <ul> <li>Maintain disciplined pipeline management, forecasting, and deal documentation in HubSpot.</li> <li>Ensure opportunities are properly qualified, structured, and progressed with clear next steps.</li> <li>Identify expansion and long-term growth opportunities within high-value accounts.</li> </ul> <p>AI-Assisted Sales Execution</p> <ul> <li>Use AI tools to support account research, discovery preparation, deal analysis, and follow-up drafting.</li> <li>Leverage call transcripts and AI-generated insights to identify objections, patterns, and next steps.</li> <li>Apply judgment to AI outputs, knowing when to rely on automation and when human decision-making is required.</li> </ul> <p>Cross-Functional Collaboration</p> <ul> <li>Collaborate with Solutions, Support, and Product teams to improve playbooks, pricing guidance, and feedback loops for strategic deals.</li> <li>Contribute structured product and market feedback based on real customer conversations.</li> </ul> <h4>Requirements: </h4> <ul> <li>6+ years of SaaS sales experience, including selling hosting-related solutions; managed hosting or WordPress hosting experience strongly preferred.</li> <li>Demonstrated success selling sophisticated, high-value solutions with longer or more consultative deal cycles.</li> <li>Experience selling to agencies, mid-market customers, or technical buyers.</li> <li>Strong discovery, consultative selling, and negotiation skills.</li> <li>Strong business acumen with the ability to connect customer needs to commercial outcomes.</li> <li>Excellent communication skills across both technical and non-technical audiences.</li> <li>Strong technical fluency, comfort, and credibility discussing WordPress, hosting, infrastructure, and platform-related concepts.</li> <li>Proven ability to negotiate creatively, manage complexity, and solve problems in a way that creates value for both the customer and the business.</li> <li>Strategic…