Outbound Account Executive

Come build the future of finance with Datarails. We’re a global, AI-powered FinanceOS company helping finance teams transform the way they work. By combining intelligent automation, AI, and seamless integrations with the tools finance teams already know and trust, we empower organizations to make faster, smarter decisions with confidence. With approximately 350 employees worldwide, we’re building the next generation of finance technology - where innovation, collaboration, and customer success go hand in hand.

If you’re looking for a fantastic opportunity to join a growing startup in a role with massive impact, we would love to meet you!

We’re hiring an Enterprise Account Executive to join our upmarket team, focused on companies with 500+ employees. This role works closely with our SDR team, taking outbound-generated, booked meetings and running the full enterprise sales cycle to close.

This position is 100% remote, based anywhere in the United States. No sponsorship or relocation assistance is available.

• Own and run the full sales cycle for enterprise (500+ employee) prospects, from SDR-booked outbound meetings through close, developing relationships, uncovering complex organizational needs, and driving adoption of our solution across multiple stakeholders
• Partner closely with your dedicated SDR(s) to sharpen targeting, messaging, and qualification criteria for outbound-generated pipeline, ensuring a high-quality, well-qualified meeting flow
• Own your forecasting and quota, delivering consistently against quarterly and annual enterprise targets
• Navigate multi-stakeholder buying committees at finance functions (CFO, VP Finance, Controllers, FP&A leaders) plus IT/Security evaluators, building consensus and creating bespoke proposals and business cases
• Manage a longer, more complex upper mid market and enterprise sales cycle with rigor, accurate Salesforce documentation, stakeholder mapping, and disciplined deal progression

• 5+ years of experience as an Account Executive selling complex B2B SaaS, ideally in enterprise/upmarket segments (500+ employees), to finance ICPs (CFO, VP Finance, Controllers) or in financial services, OR equivalent enterprise FP&A experience.
• Track record of consistently exceeding quota in an enterprise or upmarket sales motion.
• Experience working in tandem with an SDR/BDR team on outbound-sourced pipeline - you know how to give feedback that improves targeting and meeting quality, not just take meetings as handed off.
• Comfort managing longer, multi-stakeholder enterprise sales cycles, including IT/security evaluations and procurement processes.
• Strong command of CRM and sales enablement tools (Salesforce, Hub Spot, or similar) with disciplined pipeline hygiene and documentation habits.
• Ability to understand, quantify, and synthesize technical and commercial needs across a buying committee, and guide prospects to the right solution before bringing in specialized reinforcements.
• Strategic, independent self-starter who takes ownership of the role and can sell effectively against a defined framework/system.

• The base salary range for this role is $90-100k USD and generous OTE. Final offer amounts are determined by multiple factors including prior experience, value add, and location, and may vary from the amount above.
• Meaningful equity
• 401(k) plan with up to 4% match and HSA & FSA Options
• 100% paid medical, dental, and vision coverage for employees and 100% paid medical and 80% paid dental and vision coverage for dependents
• $540/year toward glasses, sunglasses, or contact lenses from XP Health for employees enrolled in any Guardian Vision plan
• Paternity leave
• Flexible, unlimited sick time and PTO (we recommend 18-25 vacation days…