Automattic Careers - Sales Account Executive, Pressable
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. • As a part of our fully distributed team, you can live in a wide range of locations around the world. Effectiveness in this role will mean occasionally shifting hours across weekends and odd hours to best coordinate with our global team. • Founded in 2010, Pressable is a world-class managed WordPress hosting provider that specializes in scalable, highly available services for agencies, builders, developers, and businesses. • With industry-leading performance, 24/7 expert support, an award-winning control panel, advanced developer tools, and seamless integrations with WooCommerce and Jetpack, Pressable provides the tools you need to reliably manage your WordPress websites with ease. We are currently looking for candidates in Latin America and North America only. • We are currently looking for candidates in Latin America and North America only. • Salary range: $90,000 - 125,000 USD OTE, with 60/40 commission split. Please note that while salary ranges are presented here in USD, we will pay in local currency.
Responsibilities
• Strategic Deal Ownership • 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. • Pipeline & Account Management • 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. • AI-Assisted Sales Execution • 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. • Cross-Functional Collaboration • 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.
Benefits
• $90,000 - 125,000 USD OTE, with 60/40 commission split • We are searching for high-caliber candidates with the skills and qualities to have a net positive for Automattic. Pay will reflect the potential contribution and the impact you can bring, which may, in some cases, go beyond the range stated. • 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. • So, are you ready to embark on this thrilling WordPress adventure? We can’t wait to welcome you to the Pressable team and empower you to make the web a better place. Come join us in crafting an exceptional customer experience and revolutionizing the world of WordPress hosting. Apply now and let’s build something amazing together!
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