Senior Sales Account Executive, Pressable

Pressable (“WordPress hosting that means business”) seeks an experienced, motivated, and empathetic professional to help drive growth across larger agency and mid-market customers as a trusted advisor for sophisticated WordPress hosting solutions.

About Pressable

Founded in 2010, Pressable is a world-class managed WordPress hosting provider specializing 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 to reliably manage WordPress websites with ease. Pressable is a subsidiary of Automattic and operates as a fully distributed team.

Responsibilities

• Strategic Deal Ownership:
  • 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.
  • Manage 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 aligning 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, to strengthen deal strategy.
  • Lead competitive positioning against alternative hosting platforms and infrastructure solutions, articulating Pressable’s differentiation in performance, support, and partnership.
  • Support successful onboarding and identify expansion opportunities by maintaining strong post-sale relationships.
  • Contribute to new business development through 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.
• 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.
  • Apply judgment to AI outputs, knowing when to rely on automation and when human decision-making is required.
• 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.

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.

Preferred Qualifications

• 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.

Schedule

This is a fully distributed role. Effectiveness may require occasionally shifting hours across weekends and odd hours to coordinate with a global team. Pressable is currently looking for candidates in Latin America and North America only.

Pay

Salary range: $140,000 - 200,000 USD OTE, with a 60/40 commission split. While salary ranges are presented in USD, payment will be made in local currency. Pay reflects potential contribution and impact, which may exceed the stated range for the right candidate.

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 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.