Senior Sales Account Executive, Pressable

Pressable (“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.

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.

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.

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.

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.
• 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.

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.

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.

About Pressable

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.

Salary range: $140,000 - 200,000 USD OTE, with 60/40 commission split. Please note that while salary ranges are presented here in USD, we will pay in local currency.

We are searching for high-caliber candidates with the skills and qualities to have a net positive for Pressable. Pay will reflect the potential contribution and the impact you can bring, which may, in some cases, go beyond the range stated for the right candidate.

Perks & Benefits of Joining Pressable!

• 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!

Pressable is a subsidiary of Automattic. We believe in Open Source, and the vast majority of our work is available under the GPL. Automattic is a Most Loved Company and an Equal Opportunity employer. If you need disability-related accommodations during the application or interview process, please fill out this form. We are committed to ensuring an accessible hiring process for all candidates. To learn about how we handle your data, please review our Privacy Policy. #LI-DNI

About Automattic 

Now in our 20th year, we’re the people behind WordPress.com, WooCommerce, Beeper, Tumblr, Simplenote, Jetpack, Longreads, Day One, PocketCasts, and more. We believe in making the web a better place.

We’re a distributed company with more than 1500 Automatticians in nearly every corner of the globe, speaking over a hundred different languages. Enriched by this diversity, we’re united by a singular mission: to democratize publishing, commerce, and messaging so anyone with a story can tell it, anyone with a product can sell it, and everyone can manage their communications from a single source. In short, we help maintain a balance in society, creating and continually refining powerful tools people can use to compete fairly—regardless of income, gender, politics, language, or where they live in the world.

We believe in Open Source, and the vast majority of our work is available under the GPL. Automattic is a Most Loved Company, an Equal Opportunity employer, and Disability Confident Committed. (Here’s what that might mean for you.) If you need accommodations during the application or interview process, please fill out this form. We are committed to ensuring an accessible hiring process for all candidates. Learn more about our Employee Resource Groups.

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All qualified applicants will receive consideration for employment without regard to race, color, religion, sex, sexual orientation, gender identity, national origin, disability, or status as a protected veteran. View the “Know Your Rights: Workplace Discrimination is Illegal” poster here. Automattic participates in the E-Verify program in certain locations, as required by law.