Enterprise Account Executive

About Fifth Dimension

Fifth Dimension is an AI-native enterprise software company transforming how the world’s largest real estate investment managers work. We automate complex document workflows, extract structured intelligence from unstructured data, and give professionals an AI workspace that replaces manual processes with 98% accuracy, where horizontal AI tools deliver 60 to 70%.

We are post-launch, in active growth, and building the sales infrastructure to match. This BDR role is foundational to that build.

At Fifth Dimension, we value ownership, experimentation, and thoughtful challenge. Our values —
Own It. Ship It. Don’t Be Boring. — guide how we build, sell, and win.

We’re hiring a New York–based Enterprise Account Executive to drive explosive growth across North America. This is a 10x sales role.

You will own and close new business with enterprise commercial real estate owners and operators, selling a transformative AI platform into sophisticated enterprise environments. If you thrive on complex, consultative sales cycles and closing six- and seven-figure deals, this is your opportunity.

Reporting into the Head of Sales, you will own the full sales cycle while helping define and refine our US go-to-market motion. This role is ideal for someone who:

• Has consistently been a top rep
• Thinks in systems and efficiency
• Tests and iterates weekly, not quarterly
• Sees a process and immediately asks, “How can I make this 3x better?”

• Own and exceed revenue targets
• Source and close complex enterprise deals
• Execute our US enterprise sales strategy across institutional CRE firms
• Build and maintain a robust, self-generated pipeline

• Design and implement personal sales methodologies that maximize output
• Develop tracking systems and metrics that demonstrate true 10x rep performance
• Build replicable playbooks that form the foundation of future team scaling

• Partner closely with Product, Solutions, and Engineering to shape roadmap direction
• Demonstrate transformational ROI
• Turn customer wins into case studies and strategic marketing assets

• Contribute to pricing, packaging, and go-to-market decisions in North America
• Support fundraising with frontline customer insights
• Help define and execute our long-term US expansion strategy

• 5+ years of enterprise sales experience
• Consistent over performance as a full-cycle Account Executive at early- to growth-stage B2B SaaS companies
• Experience selling complex, technical products (AI/ML, deeptech, fintech, or similar)
• Strong executive presence and ability to engage C-level stakeholders
• A consultative, solution-selling mindset
• Rapid iteration skills. You test, learn, and adapt constantly
• Willingness to work in-office 3x/week (Mid-town Manhattan)

• Venture-backed startup experience through multiple funding rounds
• Experience contributing to GTM strategy in scaling environments
• Proptech or CRE experience
• Advanced CRM and sales automation expertise (Hub Spot)

If you want to:

• Close big deals
• Build something lasting
• Accelerate your career
• Be part of a record-setting team

We should talk.

• $130K–$150K base salary
• Uncapped commission (targeting 50/50 OTE split)
• Meaningful equity
• 2% company-sponsored 401(k) contributions
• Healthcare, dental, life insurance
• Unlimited PTO
• $100/month wellbeing budget
• $1,000 annual training budget
• 14 weeks paid parental leave (primary caregiver)
• 6 weeks paid parental leave (secondary caregiver)
• Tailored support for exceptional life challenges (IVF, ADHD/Autism diagnosis, gender-affirming care, therapy, and more)