Senior Enterprise Account Executive - AI, US
About The Position
Fifth Dimension is hiring a Senior Enterprise Account Executive to own new business across North America, managing the full sales cycle from outbound prospecting through signature. The role sells AI-native enterprise software to institutional real estate owners, operators, and investment managers, with deals typically ranging from $250,000 to $400,000 or more in annual contract value. The position reports to the cofounder CEO and works closely with company founders and pre-sales, Product, and Engineering teams. The Account Executive will build and manage a self-generated pipeline, lead consultative sales processes with C-level and functional leaders, and guide complex deals through procurement, legal, and security review. They will help establish the US sales playbook, bring customer and deal insights into product decisions, turn customers into references and case studies, and contribute to pricing, packaging, go-to-market decisions, and fundraising insights. The company describes the position as based in its Midtown Manhattan office three days a week, while also stating that the role is remote in the US.
Requirements
- At least 5 years of enterprise sales experience, consistently exceeding quota as a full-cycle Account Executive at early- to growth-stage B2B SaaS companies.
- Track record as a top sales representative more than once, including selling products that are difficult to explain and reaching challenging buyers.
- Experience selling complex technical products, such as AI/ML, deeptech, or fintech products.
- Ability to engage C-level stakeholders without relying on a solutions engineer as a crutch.
- Experience navigating six- and seven-figure deals through procurement, legal, and multi-stakeholder approval.
- Uses an instrumented, data-driven sales process that is tested and revised regularly.
- Can independently build sales decks and prepare for calls without relying on enablement teams or existing materials.
- Comfort thriving in an early-stage environment with limited playbooks and case studies and broad responsibilities.
- The posting specifies working in the Midtown Manhattan office three days a week.
Nice To Haves
- Venture-backed startup experience through multiple funding rounds.
- Experience shaping go-to-market strategy in a scaling environment.
- Experience selling to institutional real estate, private-markets, or real-assets buyers.
- Deep HubSpot and sales automation expertise.
Responsibilities
- Source, run, and close $250,000 to $400,000+ ACV deals with institutional real estate owners, operators, and investment managers.
- Build and own a self-generated pipeline.
- Run consultative, multi-stakeholder sales cycles with C-level buyers and heads of function, including procurement, legal, and security review.
- Partner with pre-sales to deliver live demonstrations using prospects’ own data.
- Develop the sales playbook, including qualification, messaging, sequencing, and deal reviews.
- Share deal intelligence with Product and Engineering to influence product development.
- Turn wins into reference customers, case studies, and proof points.
- Contribute to pricing, packaging, and US go-to-market decisions, and provide frontline customer insight for fundraising.
- Build and manage outbound sequences, monitor their performance, and improve them based on results.
- Develop business cases, navigate negotiations, and close enterprise deals.
Benefits
- Uncapped commission; target compensation is a 50/50 base and commission split.
- Meaningful equity on a standard vesting schedule.
- Company-sponsored 401(k) contributions of 2%.
- Company-sponsored medical, dental, and life insurance.
- Unlimited paid time off.
- $100 monthly wellbeing budget.
- Contributions toward gender-affirming care, private specialists and scans, ADHD/autism diagnosis, IVF, and therapy.
- 14 weeks of fully paid parental leave for primary caregivers and six weeks for secondary caregivers.
- $1,000 annual training budget.
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What This Job Offers
Job Type
Full-time
Career Level
Senior
Education Level
No Education Listed
