Enterprise Sales Executive (Technical Sales)

Role Type: Full-time

Reporting To: Vice President of Business Development

Position Status: Newly created

Work Model: Hybrid

Base Salary Range: $80,000–$88,000

Recruitment Partner: This position is being hired in partnership with one of Drake International’s clients.

We are seeking a high-performing Enterprise Sales Executive with strong technical fluency. You will lead complex, multi-stakeholder mid-market and enterprise sales cycles while confidently supporting the technical evaluation process—clarifying requirements, shaping workable solutions, tailoring demos, and guiding integration conversations. This role is well-suited for a commercially driven seller who excels at the intersection of business value, product capability, and technical credibility.

Qualifications

• 5–7+ years of experience in B2B SaaS, subscription-based software, payments (AR), fintech, or closely related cloud platform environments.
• Demonstrated appetite for proactive outbound sales, including building new relationships, developing account entry points, and generating net-new pipeline.
• Proven success closing mid-market and enterprise deals, typically $100K+ ARR or equivalent.
• Strong command of multi-stakeholder sales motions involving Finance, Operations, Technology, Product, and Procurement.
• Functional understanding of APIs, integrations, data workflows, and platform architecture (no coding required), including how solutions connect with systems such as Salesforce, HubSpot, NetSuite, QBO, Geotab, and Avalara.
• Experience delivering structured demos and guiding customers through technical evaluations.
• Skilled in structured sales methodologies such as MEDDICC, Challenger, SPIN, or value-based selling.
• Strong negotiation capability and comfort navigating commercial, legal, and procurement stages.
• Excellent communication skills with the ability to articulate complex concepts clearly to both executive and technical audiences.
• High degree of CRM discipline with accurate forecasting and pipeline hygiene.
• Ability to collaborate effectively with Sales Engineering, Product, and Customer Success.

Responsibilities

• Lead full-cycle enterprise sales motions from prospecting and qualification through negotiation and close.
• Conduct deep discovery to understand business drivers, operational needs, and technical requirements.
• Deliver tailored presentations, demos, and ROI-based proposals aligned with stakeholder priorities.
• Communicate platform capabilities—including integrations, data flows, architecture, and workflow impacts—in clear business terms.
• Partner with Sales Engineering to shape solution design, validate feasibility, and support technical assessments.
• Support RFP/RFI processes with structured commercial and technical input.
• Build and manage strategic account plans that support pipeline growth and multi-year expansion opportunities.
• Engage with Product and Engineering teams to bring forward customer insights and influence roadmap alignment.
• Maintain strong forecasting accuracy, CRM documentation, and data-driven reporting.
• Ensure seamless handoff to Customer Success and Implementation teams with clear, well-informed expectations.

What We Offer

• Competitive base salary commensurate with experience ($80,000–$88,000), plus a variable compensation plan aligned with performance.
• Hybrid work environment with flexibility to balance in-office and remote work.
• Three (3) weeks’ vacation annually, plus dedicated sick days and wellness days.
• Comprehensive health and dental benefits, with additional extended coverage.
• Opportunity to shape customer strategy in a high-impact, commercially focused role.
• Ideal start date: January 15th.About Drake International

Since 1951, Drake International has been a global leader in flexible and permanent staffing, connecting people with meaningful work at every career stage. We collaborate directly with employers to bring you the best opportunities at no cost, ensuring a people-first experience where everything works seamlessly.

Drake International is an equal opportunity employer and champions accessibility, inclusivity, and diversity in the workplace. We are committed to providing accommodation for applicants with disabilities throughout the recruitment process. If you require accommodation, please contact your local Drake representative.

AI Disclosure

While Drake International uses certain AI-enabled systems to support administrative efficiency, all screening, assessment, and selection decisions for this role are made by a human. Every application for this position is personally reviewed by the recruiter managing this search. No automated decision-making or AI-driven filtering is used at any stage of the hiring process.