Note: The job is a remote job and is open to candidates in USA. Datarails is a global, AI-powered FinanceOS company helping finance teams transform how they work through intelligent automation, AI, and integrations. The Outbound Account Executive will manage the full enterprise sales cycle for outbound-generated opportunities, partnering with SDRs, navigating complex stakeholder groups, forecasting quota, and closing deals with companies of 500 or more employees.
Responsibilities
- 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
Skills
- 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, HubSpot, 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
- This position is 100% remote, based anywhere in the United States. No sponsorship or relocation assistance is available
Benefits
- 100% remote, based anywhere in the United States
- Generous OTE
- Meaningful equity
- 401(k) plan with up to 4% match
- HSA & FSA Options
- 100% paid medical, dental, and vision coverage for employees
- 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 annually)
- 12 paid company holidays
- Life insurance
- CPA/CFA license renewal reimbursement
Company Overview