Senior Enterprise AI & SaaS Sales Executive

Jobtailor; Boston (MA); On-site; USD 120,000 - 200,000; Full time

Job summary

Jobtailor is seeking an experienced Enterprise B2B sales professional in Boston to own the full sales cycle from discovery to close, building relationships with senior executives across enterprise accounts and positioning REAL as a strategic AI solution.

You will develop account strategies, manage multi-threaded opportunities, run product demonstrations, and collaborate with SDR, CS, Product, and Leadership to drive go-to-market efforts.

Qualifications

• 5+ years of Enterprise B2B sales experience with a track record of closing complex deals.
• Experience selling AI, SaaS, enterprise software, or data-driven technology solutions.
• OR experience as a Commercial Real Estate Broker, Retail Broker, or in another customer-facing commercial real estate advisory role.
• Strong consultative selling and relationship-building skills.
• Experience managing long enterprise sales cycles with multiple stakeholders.
• Excellent presentation, negotiation, and communication skills.
• Highly self-motivated with strong ownership and execution.
• Comfortable working in a fast-growing startup environment with changing priorities.
• Experience using CRM platforms such as HubSpot or Salesforce.

Responsibilities

• Own the full enterprise sales cycle, from discovery through negotiation and close.
• Build relationships with senior executives and multiple stakeholders across enterprise accounts.
• Understand customer business challenges and position REAL as a strategic AI solution.
• Develop account strategies and manage complex, multi-threaded sales opportunities.
• Partner closely with SDRs, Customer Success, Product, and Leadership throughout the sales process.
• Deliver product demonstrations and business presentations tailored to customer needs.
• Accurately manage pipeline, forecasts, and customer activity in the CRM.
• Stay up to date on AI, commercial real estate, and enterprise technology trends.
• Represent REAL as a trusted advisor throughout the customer journey.
• Help shape our go-to-market strategy by sharing customer insights and market feedback.

Skills

Enterprise B2B sales

Consultative selling

Relationship-building

Presentation skills

Negotiation

Communication skills

Self-motivation

Adaptability

Account strategy

Tools

HubSpot CRM

Salesforce

Job description

Jobtailor is seeking an experienced Enterprise B2B sales professional in Boston to own the full sales cycle from discovery to close, building relationships with senior executives across enterprise accounts and positioning REAL as a strategic AI solution.

You will develop account strategies, manage multi-threaded opportunities, run product demonstrations, and collaborate with SDR, CS, Product, and Leadership to drive go-to-market efforts.