Senior Sales Account Executive
$140,000–$200,000 year
Remote
Job Summary
Own and manage complex agency and mid-market hosting opportunities from discovery through negotiation, acting as a trusted advisor to technical and executive stakeholders. Lead deep discovery sessions to understand customer goals, develop tailored proposals and pricing strategies, and coordinate cross-functional partners to drive multi-stakeholder deals to close. Maintain disciplined pipeline management in HubSpot while leveraging AI tools to enhance research, deal analysis, and follow-up efficiency. Proactively execute outbound plans for named account mapping and identify expansion opportunities within high-value existing accounts. This role supports Pressable's growth as a managed WordPress hosting provider, requiring occasional weekend or odd-hour shifts to align with a global distributed team.
Required Qualifications
- 6+ years of SaaS sales experience
- 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
- Effectiveness in occasionally shifting hours across weekends and odd hours to best coordinate with a global team
- Candidates in Latin America and North America only
Desired Qualifications
- Managed hosting or WordPress hosting experience
- Experience selling to agencies, developers, or infrastructure-aware customers
- Experience working in sales environments that leverage AI for efficiency and insight
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