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Salary: USD 130,000 - 400,000 / annual
Fifth Dimension AI is an AI-native enterprise software company transforming how the world's largest real estate investment managers work. The company automates complex document workflows, extracts structured intelligence from unstructured data, and delivers an AI workspace that replaces manual processes with 98% accuracy—significantly outperforming horizontal AI tools at 60-70% accuracy.
You will own new business across North America on a full-cycle basis, reporting directly to the cofounder CEO. This is a high-autonomy role where you will source, run, and close $250k to $400k+ ACV deals with institutional real estate owners, operators, and investment managers.
Day-to-day responsibilities include:
- Source and build a self-generated pipeline; you own the number for North America
- Run consultative, multi-stakeholder sales cycles with C-level buyers and heads of function through procurement, legal, and security review
- Partner with pre-sales to deliver live demos on prospects' own data
- Build and document the sales playbook: qualification, messaging, sequencing, and deal reviews that become the standard for the US team
- Carry deal intelligence into Product and Engineering to shape the product roadmap
- Turn wins into reference customers, case studies, and proof points that accelerate future cycles
- Contribute to pricing, packaging, and US go-to-market strategy
- Work in the Midtown Manhattan office three days per week
This is an early-stage role where there is no existing playbook, a thin case-study library, and everyone wears multiple hats. You will be one of the first enterprise sellers in NYC, and the reps hired after you will sell the way you decide they should.
Fifth Dimension is backed by top-tier American and European investors, closed a Series A at $26 million, and operates globally with offices in London, New York, and Singapore. The team is 30 people with a culture centered on Own It, Ship It, and Don't Be Boring.
REQUIREMENTS:
- 5+ years of enterprise sales, consistently over quota as a full-cycle Account Executive at early- to growth-stage B2B SaaS companies
- Proven track record as a top rep at companies where the product was hard to explain and the buyer was hard to reach
- Experience selling complex, technical products (AI/ML, deeptech, fintech, or similar) and ability to hold a room of C-level stakeholders without relying on a solutions engineer
- Demonstrated success navigating six- and seven-figure deals through procurement, legal, and multi-stakeholder sign-off
- Ability to run your sales process like an engineer: instrumented, tested weekly, rebuilt based on data
- Self-sufficiency: build your own decks, prep your own calls, don't wait for enablement teams or materials
- Comfort thriving in chaos with minimal structure and playbooks
Bonus qualifications:
- Venture-backed startup experience through multiple funding rounds
- Experience shaping GTM strategy in a scaling environment
- Background selling to institutional real estate, private markets, or real-assets buyers
- Deep HubSpot and sales automation expertise
