Outbound Account Executive

Datarails; Northern (KY); Hybrid; USD 90,000 - 100,000; Full time

Benefits offered by this job

Equity

401(k) with match

HSA & FSA Options

Medical, dental, and vision coverage

Glasses allowance

Paternity leave

Paid time off

Company holidays

Life insurance

Job summary

Datarails, a global AI-powered FinanceOS company, is hiring an Account Executive to own the full sales cycle from outbound meetings to close. You will engage finance leaders and IT stakeholders, tailoring proposals to complex needs and driving adoption of our finance automation platform.

This 100% remote US-based role collaborates with SDRs, targets upmarket accounts, manages forecasts in Salesforce, and delivers against quarterly quotas.

Qualifications

• 5+ years as an Account Executive selling complex B2B SaaS to finance ICPs.
• Proven track record of exceeding quota in upmarket sales motions.
• Experience collaborating with SDR/BDR teams on outbound pipeline.
• Comfort handling long, multi-stakeholder sales cycles including IT/security.
• Strong CRM discipline and documentation habits.

Responsibilities

• Own and run full sales cycle from outbound meetings to close.
• Partner with SDRs to sharpen targeting and qualification criteria.
• Own forecasting and quota delivery with accurate Salesforce records.
• Navigate finance buying committees and IT/security evaluations.
• Develop bespoke proposals and business cases for prospects.

Skills

Account Executive

B2B SaaS

Quota attainment

Sales cycle mgmt

CRM tooling

Tools

Salesforce

HubSpot

Job description

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 anAccount Executive to join our upmarket team. This role works closely with our SDR team, taking outbound-generated, booked meetings and running the full sales cycle to close.

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

What You’ll Do

• Own and run the full sales cycle for 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 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 sales cycle with rigor, accurate Salesforce documentation, stakeholder mapping, and disciplined deal progression

Requirements

• 5+ years of experience as an Account Executive selling complex B2B SaaS, ideally in upmarket segments to finance ICPs (CFO, VP Finance, Controllers) or in financial services, OR equivalent FP&A experience.
• Track record of consistently exceeding quota in 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 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.

What we offer:

• 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 annually)
• 12 paid company holidays
• Life insurance

We want to make sure everyone has an equal chance to participate and make a difference. Datarails is an equal opportunity employer and prioritizes building a diverse and inclusive workplace. We provide equal employment opportunities to all employees and applicants of any type and do not discriminate based on race, color, religion, national origin, gender, age, sexual orientation, physical or mental disability, genetic information or characteristic, gender identity and expression, veteran status, or other non-job related characteristics or other prohibited grounds specified in applicable federal, state, and local laws. Datarails’ policy is to comply with all applicable laws related to nondiscrimination and equal opportunity and will not tolerate discrimination or harassment based on any of these characteristics. This policy applies to all terms and conditions of employment, including recruiting, hiring, placement, promotion, termination, layoff, recall, transfer, leaves of absence, compensation, and training.