Senior Sales Account Executive

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Pressable

WebsiteLinkedInAll Job Openings

51 - 200 employees

Founded 2010

☁️ SaaS

🤝 B2B

🏢 Enterprise

💰 $1.5M Venture Round - Pressable on 2015-04

SaaS • B2B • Enterprise

Pressable is a managed WordPress hosting provider built on Automattic’s WP Cloud that delivers enterprise-grade, autoscaling cloud infrastructure and a global CDN for WordPress and WooCommerce sites. It offers managed hosting plans and white‑label solutions for agencies, developer‑friendly tools (SSH, Git, WP‑CLI), free expert migrations, 24/7 WordPress expert support, and security features (Jetpack Security, WAF, backups). Pressable also provides an AI-powered management product (Pressable MCP) to automate site creation, configuration, monitoring, and other WordPress workflows. Customers include agencies, ecommerce stores, high‑traffic and enterprise sites.

📋 Description

• 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.

🏖️ Benefits

• Health Benefits for US-based staff (99% Paid Employee Medical, Dental, and Vision). • Matching 401(k) for US-based staff. • Life and Disability Insurance for US-based staff (100% Paid Life & LTD). • Work from home with a home office setup and coworking allowances. • Open vacation policy (no set number of days per year). • Hardware and software, books or conferences that promote continued learning.