Senior Sales Account Executive

Automattic

Sales Account Executive for Pressable driving growth in mid-market and agency sectors through consultative sales. Building relationships and managing complex sales cycles with a focus on WordPress hosting.

Posted 7/21/2026full-timeRemote • 🇺🇸 United StatesSenior💰 $140,000 - $200,000 per yearWebsite

Core Competencies

Role fit

Core Competencies

Use this summary to align your resume positioning with the role.

Demonstrates expertise in SaaS sales with a focus on hosting solutions, particularly WordPress hosting, while effectively managing complex sales cycles and multi-stakeholder engagements. Exhibits strong negotiation, consultative selling, and strategic planning skills to align customer needs with business outcomes.

Highest-signal resume keywords

SaaS Sales ExperienceWordPress Hosting KnowledgeConsultative Selling SkillsNegotiation StrategyCRM Proficiency (HubSpot)

ATS Keywords

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Applicant Tracking System Keywords

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Hard Skills

SaaS SalesConsultative SellingNegotiationTechnical FluencyPipeline ManagementDeal StructuringMarket AwarenessProposal DevelopmentRevenue Quota ManagementComplex Solution Selling

Soft Skills

Communication SkillsBusiness AcumenCollaborationJudgmentAdaptability

Tools & Technologies

HubSpotAI Sales ToolsCRM Systems

Industry Keywords

Managed HostingMid-Market SalesAgency SalesTechnical BuyersCompetitive Positioning

Tech Stack

Tools & technologies

WordPress

About the role

Key responsibilities & impact

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

What you’ll need

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

Comp & perks

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.