Outbound Account Executive

Datarails; United States; Remote; USD 90,000 - 100,000; Full time

Benefits offered by this job

Equity

Base salary $90-100k USD + OTE

401(k) with up to 4% match

Medical, dental, and vision coverage

Paternity leave

Paid time off and holidays

Remote work

Job summary

Datarails is hiring an Enterprise Account Executive to own the full enterprise sales cycle for 500+ employee prospects, from outbound meetings to close. This 100% remote role targets CFOs, VP Finance, and IT evaluators across multi-stakeholder deals.

You will partner with SDRs, manage forecasting, and keep a clean Salesforce/HubSpot pipeline. The base salary is $90k–$100k USD with generous OTE and equity.

Qualifications

• 5+ years of experience in enterprise B2B SaaS sales to finance ICPs.
• Proven track record of exceeding quarterly/annual quotas.
• Experience partnering with SDR/BDR teams on outbound pipeline.
• Ability to navigate multi-stakeholder IT/security and procurement processes.
• Strong familiarity with CRM and sales enablement tools and disciplined documentation.

Responsibilities

• Own and run the full sales cycle for enterprise prospects (500+ employees) from outbound meetings to close.
• Collaborate with SDRs to sharpen targeting, messaging, and qualification criteria for outbound pipeline.
• Own forecasting and quota attainment, delivering against targets.
• Navigate buying committees across CFO, VP Finance, Controllers, FP&A and IT/security evaluators.
• Maintain accurate Salesforce documentation and a disciplined deal progression.

Skills

Enterprise sales

Quota attainment

CRM proficiency

Cross-functional collaboration

Outbound activity

Tools

Salesforce

HubSpot

Job description

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 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.

What You’ll Do

• 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

Requirements

• 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.

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
• CPA/CFA license renewal reimbursement

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.