Senior Pre-Sales Engineer

Monday. A $400k deal with a REIT’s VP of Technology closes next month. You’re building a custom AI workspace with their actual portfolio data: their buildings, their leases, their numbers on screen for tomorrow’s demo.

Tuesday. Live demo. Their CTO asks how your AI evaluation framework compares to generic benchmarks. You walk through domain-specific evals, pull up accuracy metrics in real time, and show 98% lease abstraction accuracy on their documents. The room goes quiet.

Wednesday. Discovery call with a prospect who “already has ChatGPT Enterprise.” You show them what 65% accuracy looks like on a real lease abstract versus 98%, and why the gap matters when you’re managing a $2 billion portfolio. They ask for a follow-up with their data team.

Thursday. You draft the security response to their RFP. You map a competitor’s technical gaps on a battle card for the AE team. You know where the gaps are because you’ve been in the room with the buyer.

Friday. Pipeline review with the sales team. Three deals need technical depth next week; you’re prioritizing by deal size and close probability. One AE needs coaching on how to position the data integration story to a CFO.

This is pre-sales engineering at Fifth Dimension. You are the technical voice in every deal that matters. You build trust with CTOs. You drive unit economics, ensuring what’s good for our partners and what’s good for us align beautifully. Revenue depends on you.

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.

You own the technical side of winning enterprise deals across the US. First dedicated pre-sales hire. Reporting directly to the CPO.

Day to day, you will:

• Lead technical discovery and scoping with prospects, translating their requirements into solution architecture and implementation plans that close deals

• Build and run live demos with prospect-specific data, making the technical case so compelling that procurement becomes a formality

• Own RFP/RFI responses and security questionnaires: the technical collateral that gets deals through procurement

• Build the pre-sales playbook, demo environments, battle cards, and competitive positioning from humble beginnings

• Partner with AEs to prioritize pipeline, coach on technical positioning, and ensure every high-value conversation has technical depth

• Bridge won deals to the implementation team with clean handoffs and scoped requirements

• Carry the voice of prospect technical requirements into Product and Engineering, shaping the roadmap with deal intelligence

• Unite longterm product vision from the founders with daily deal implementation and sales

• Travel 25 to 30% to prospect and client sites across the US

You sell to CTOs. You walk into a room and earn technical credibility in the first 5 minutes. Your pre-sales work closes deals.

• You discuss what differentiates 5D from marketplace competitors (horizontal and vertical) with ease. You know how to go toe-to-toe with CTOs on LLMs, RAG, security architecture, and data pipelines. No prep sheet required.

• You build and run live demos with their actual data.

• You’ve navigated $250k+ deals through procurement, legal, and multi-stakeholder sign-off.

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

• While we’ve had solutions engineers help out with pre and post sales, you’re building out the pre sales function as one of the first in the role. There’s no set playbook, the demo library is spotty, and everyone’s wearing 1000 hats. You thrive in that chaos.

• Track record of shortening sales cycles.

Bonus points:

• You’ve been the first or founding pre-sales / SE hire at a startup

• Real estate, financial services, or professional services domain knowledge

• Coding ability (Python, SQL) to build custom demo environments and proof-of-value scripts

• Experience at an AI-native or data platform company

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: $170,000 to $220,000 base + variable (up to $290,000 OTE) depending on experience

• 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

Most pre-sales roles slot you into an existing machine. This one asks you to build it.

You will be the first senior pre-sales hire in NYC selling $250,000 to $400,000 ACV deals to marquee enterprise customers. You will work shoulder-to-shoulder with the founders on the highest-value deals. You will set the standard for everyone who follows.

The product sells itself when demoed well. 98% accuracy on lease abstraction, where ChatGPT delivers 65%, is not a talking point; it’s a live demonstration that silences a room. Your job is to put that demonstration in front of every CTO who matters.

Series A closed at $26 million. The team is 40 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.