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Outsiders Fund

Head of Business Development

northern, KY

Check who can apply and the requirements below before continuing.

About this opportunity

Outsiders Fund lists this Head of Business Development opportunity in northern, Kentucky. Review the employer’s description below for duties, qualifications and application requirements.

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

Build!

Recruit, onboard, coach and develop a high-performing UK BDR team

Own the day-to-day performance of the BDR function, setting clear expectations around activity, qualified meetings, pipeline generation and conversion

Build a strong outbound culture centered around quality, accountability, consistency and continuous improvement

Run regular 1:1s, call coaching, team meetings, performance reviews and development conversations

Use activity, conversion and pipeline data to identify performance gaps and improve results across the funnel

Work closely with Account Executives to develop account strategies, coordinate outbound activity and maintain high-quality opportunity handovers

What Sets You Up for Success

Hardcore work ethic and high agency

Proven experience managing BDRs or SDRs within a B2B SaaS or technology company.

Strong understanding of modern outbound prospecting, particularly cold calling, email, LinkedIn and account-based approaches

Previous success in an individual pipeline-generation or closing sales role, giving you first‑hand understanding of what strong prospecting looks like

Strong coaching skills with the ability to identify why someone is underperforming and turn that diagnosis into practical improvement

Experience building or improving sales processes, messaging, sequences, qualification frameworks or outbound playbooks

High expectations of yourself and your team, combined with the ability to coach people constructively and help them improve

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

Nice to have

Experience selling ERP, accounting software, fintech, financial management software or another complex business application

Experience prospecting into CFOs, Finance Directors, Financial Controllers or other senior finance stakeholders

Experience helping build or scale a new market, territory or sales development function.

Experience working within an early-stage or high-growth US SaaS company expanding internationally

Meet the Team

David Ryan has closed 160% of his quota in his first quarter and got promoted to a Sales Manager

Sam Bush closed his first deal in 28 days since his start date

Wyatt Myers has been building our West Coast presence by organizing events for finance leaders, most recently a poker night that turned attendees into channel partners and warm intros

Compensation & Benefits

Equity: $40,000 - $55,000

Base Salary: $120,000 - $160,000

Commission: $40,000 - $60,000 (uncapped)

OTE: $160,0000 - $220,000

Medical, dental & vision insurance

One Medical membership

Mental health support (Talkspace)

Fertility & family-building support (Kindbody)

Virtual healthcare (Teladoc Health)

401(k) benefits

Commuter benefits

Learning & development budget for courses, certifications & language learning

Unlimited AI tokens

AI skills development & enablement

Visa & permanent residence sponsorship

Relocation support for employees moving to New York

Flexible PTO (27 days, including public holidays)

Collaborative, in‑office culture with no bureaucracy

Snacks, drinks, team events & more

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Who can apply

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