Senior Enterprise Account Executive - AI, New York

What a week looks like

Monday. Pipeline review. Fourteen live opportunities, four in late stage. A $350k deal with a global investment manager's Head of Asset Management has gone quiet since legal picked it up. You call their General Counsel directly rather than waiting on your champion.

Tuesday. First meeting with the COO of a REIT that "already has ChatGPT Enterprise." You don't argue. You ask how long their last lease abstraction took, what it cost, and what happened when the numbers were wrong. Then you book the pre-sales engineer to run 5D on their own documents next week.

Wednesday. Procurement at a $2 billion fund wants 40% off. You hold the price, restructure the phasing, and get the CFO on a call. You know the ROI cold because you built the business case with them.

Thursday. Two hours with the CTO and the pre-sales engineer, working through what three prospects asked for that the product doesn't do yet. One of them is worth building. You say which, and why.

Friday. Verbal on the $350k. You draft the case-study ask before the contract is signed. Then you rebuild your outbound sequence: last week's reply rate was 6%, and you have a hypothesis for getting it to 10.

This is enterprise sales at Fifth Dimension. You own the number for North America. You sell to the people who run the firms that finance and manage the built world. Revenue depends on you.

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 a global company with offices in London, New York, and Singapore, backed by top-tier American and European investors. Our founders, Johnny Morris and Dr. Kate Jarvis, bring a powerful combination: Johnny has more than 18 years applying data and analytics to real estate, while Kate holds a Stanford PhD and 12 years of executive experience across Silicon Valley and London.

Our values are Own It, Ship It, and Don't Be Boring. We are demanding and encouraging in equal measure. We experiment, we challenge each other, and we ship daily.

What you'll do

You own new business across North America, full cycle, from first outbound to signature. Reporting to the cofounder CEO.

Day to day, you will:

• Source, run, and close $250k to $400k+ ACV deals with institutional real estate owners, operators, and investment managers

• Build and own a self-generated pipeline. You don't wait for marketing leads that don't exist yet

• Run consultative, multi-stakeholder cycles with C-level buyers and heads of function, through procurement, legal, and security review

• Partner with pre-sales to put live demos on prospects' own data in front of every buyer who matters

• Build the playbook: qualification, messaging, sequencing, deal reviews. What you write down becomes how the US team sells

• Carry deal intelligence into Product and Engineering, shaping what gets built next

• Turn wins into reference customers, case studies, and the proof points that shorten the next cycle

• Contribute to pricing, packaging, and US go-to-market decisions, and feed frontline customer insight into fundraising

What we're looking for

You've been the top rep, more than once, at companies where the product was hard to explain and the buyer was hard to reach. You close.

• 5+ years of enterprise sales, consistently over quota as a full-cycle AE at early- to growth-stage B2B SaaS companies

• You've sold complex, technical products (AI/ML, deeptech, fintech, or similar) and can hold a room of C-level stakeholders without a solutions engineer as a crutch

• You've navigated six- and seven-figure deals through procurement, legal, and multi-stakeholder sign-off

• You run your sales process like an engineer: instrumented, tested weekly, rebuilt when the data says so

• You build your own decks, prep your own calls, and don't wait for enablement teams or materials that don't exist yet

• There's no playbook, the case-study library is thin, and everyone's wearing 1000 hats. You thrive in that chaos

• In the Midtown Manhattan office three days a week

Bonus points:

• Venture-backed startup experience through multiple funding rounds

• You've shaped GTM strategy in a scaling environment

• Sold to institutional real-estate, private-markets or real-assets buyers

• Deep HubSpot and sales automation expertise

What we offer

We're building something extraordinary and we want extraordinary people. Our benefits go beyond the standard: from tailored support for life's challenges (IVF, gender-affirming care, ADHD diagnosis, and more) to meaningful parental leave.

• Compensation: $130,000 to $150,000 base + uncapped commission, targeting a 50/50 split ($260,000 to $400,000 OTE at target)

• Equity: Meaningful, on a standard vesting schedule

• 401(k): 2% company-sponsored contributions

• Healthcare: Company-sponsored medical, dental, and life insurance

• PTO: Unlimited

• Wellbeing: $100 monthly budget

• Tailored support: Contributions to gender-affirming care, private specialist and scans, ADHD/autism diagnosis, IVF, and therapy

• Parental leave: 14 weeks full pay (primary caregiver), six weeks full pay (secondary caregiver)

• Training: $1,000 annual budget

Why this role

Most AE roles hand you a territory and a playbook. This one asks you to write the playbook.

You will be one of the first enterprise sellers in NYC, closing $250,000 to $400,000 ACV deals with marquee institutional customers and working directly with the founders on the biggest ones. The reps hired after you will sell the way you decided they should.

The product does the hard part when demoed well. 98% accuracy on lease abstraction, where ChatGPT delivers 65%, silences a room. Your job is to get into that room, and out of it with a signature.

Series A closed at $26 million. The team is 30 people. No bureaucracy. Ship daily. NYC hybrid office.

If you embody Own It, Ship It, and Don't Be Boring, we want to hear from you.