Enterprise Account Executive

Outsiders Fund; New York, Northern (NY, KY); Hybrid; USD 271,000 - 352,000; Full time

Benefits offered by this job

Equity

Private medical insurance

Mental health support

Fertility support

Group life insurance

Pension with salary sacrifice

Flexible PTO

Relocation support to NYC

Visa sponsorship

AI token usage

Learning & development budget

Job summary

DualEntry is hiring for a senior enterprise sales leader based in New York, with visa sponsorship and relocation support after two years. You will own the full sales cycle for high-value deals ($100K+ ACV) across finance, IT, and executives, leveraging MEDDPICC to win complex opportunities and shape the product roadmap with the founders.

You’ll join an early team with significant equity and a direct impact on GTM strategy, reports to leadership, and operates in a high-speed, high-trust

Qualifications

• 7+ years in sales with 5+ years closing enterprise deals ($100K+ ACV)
• Fluency in formal sales methodologies (MEDDPICC/MEDDIC/Command of the Message)
• Experience selling into finance, accounting, or ERP buyers is a plus
• Experience in early-stage startups and building process rather than inheriting it
• Entrepreneurial mindset with ownership over deals and processes

Responsibilities

• Own the full enterprise sales cycle from prospecting to close across multiple economic buyers
• Cultivate relationships across finance, IT, security, and executives
• Run deals using MEDDPICC or similar framework
• Lead internal teams through complex, multi-stakeholder processes
• Navigate procurement, security reviews, and legal negotiations
• Partner with BDRs to develop and prioritize enterprise pipeline
• Identify target personas and tailor outreach to build pipeline
• Create playbooks, talk tracks, and battlecards for the team
• Own forecasting and pipeline accuracy for your book of business
• Influence GTM strategy and the product roadmap with founders

Skills

Enterprise sales

MEDDPICC

Multi-stakeholder deals

GTM strategy influence

Finance/ERP domain

Startup scaling

Tools

MEDDPICC framework

Job description

About DualEntry

DualEntry is building the OS for finance.

Every business needs a financial system of record, yet the world's largest fintech market ($220B+) still runs on software from the 1990s. DualEntry's AI-native ERP automates accounting from data entry to close, so finance teams move faster, spend less and incur less risk.

In just 2 years we've raised $100M+ from Lightspeed, Khosla Ventures, Contrary and Google Ventures and earned the trust of customers from $5M ARR to publicly traded companies.

We hire outliers - people who have achieved difficult things, in their careers or beyond. You'll find leaders, colleagues who've competed at the highest levels of sport, performed on Broadway, trained with UFC champions and founded the country’s largest Python community.

Where You'll Create Impact

• Own the full enterprise sales cycle: prospecting through close, on complex deals multiple economic buyers

• Multi-thread every opportunity: build relationships across finance, IT, security, and executive sponsors

• Run deals with MEDDPICC or an equivalent framework

• Manage internal teams through complex, multi-stakeholder sales processes

• Navigate procurement, security reviews, and legal negotiations to close

• Partner with BDRs to develop and prioritize enterprise pipeline

• Identify target personas within top accounts and customize outreach to build pipeline

• Build the playbook: talk tracks, battlecards, and the deal patterns others on the team will run

• Own forecasting and pipeline accuracy for your book of business

• Have real influence on GTM strategy and the product roadmap, working directly with founders

What Sets You Up for Success

• Hardcore work ethic and high agency

• 7+ years in sales, with 5+ years as an individual contributor closing enterprise deals ($100K+ ACV, multi-stakeholder, 6+ month cycles)

• Fluency in a formal sales methodology (MEDDPICC, MEDDIC, Command of the Message, or similar) and a track record of applying it to win complex deals

• Experience selling into finance, accounting, or ERP buyers a plus

• You have sold at early-stage startups, building process rather than inheriting it

• Open to non-traditional backgrounds with finance or accounting experience

• An entrepreneurial mindset and willingness to take radical ownership over deals and process

Why You’ll Thrive Here

• Significant equity ownership in one of the top AI companies in the world

• You’re joining early and will grow with DualEntry

• Your feedback shapes the product directly

• High-speed, high-trust environment with high expectations

Meet the Sales Team

• Sam Bush closed his first deal 28 days after his start date

• Andy Woods, Head of Product: under his leadership the team shipped 29 projects and 325+ features in a single cycle, rebuilt bank connections and reporting infrastructure, and launched an AI accounting copilot. Kicked off DualEntry's Ctrl+AI series, walking the company through how we think about building AI-native workflows.

• David Ryan closed 160% of his quota in his first quarter and was promoted to Sales Manager

Compensation & Benefits

• Equity: £30,000 - £40,000

• Base salary: £100,000 - £130,000

• Commission: £100,000 - £130,000 (uncapped)

• OTE: £200,000 - £260,000

• Private medical insurance through Freedom Elite

• Mental health support (Talkspace)

• Fertility support (Carrot)

• Group life insurance (Allianz)

• Workplace pension through Penfold (with salary sacrifice option)

• Flexible PTO (28 days, including public holidays)

• Unlimited AI token usage

• AI skills development & enablement

• Learning & development budget for courses, certifications & language learning

• Visa sponsorship and relocation support for a move to NYC (after 2 years' tenure)

• In-person team meetups (our last ones: Lisbon, Vienna, Warsaw, Cyprus, and more!)

- David Ryan, Sales Manager at DualEntry