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 convert qualified prospects into customers through a consultative, solution-oriented sales approach. This role is responsible for managing opportunities from discovery through close, building strong customer relationships, and helping prospects select the right solution for their business needs.

The SAE is a full-cycle seller focused on high-value new business opportunities across Pressable’s target market. You will work with both inbound and self-generated opportunities, run a disciplined sales process, and drive deals forward with strong discovery, solution alignment, and commercial execution. The role requires technical fluency, solid business judgment, and the ability to build trust with prospective customers while moving opportunities efficiently from initial engagement through close.

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.

This is a senior individual contributor role designed for someone who thrives in longer sales cycles, multi-stakeholder environments, and consultative selling motions. 

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.
• 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: 

• 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.

Preferred Qualifications:

• 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: $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.

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.

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.

You can track your application status and more at MyGreenhouse.

To learn about how we handle your data, please review our Privacy Policy.

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.