Regional Director, Enterprise

Fivetran; Illinois; Hybrid; USD 180,025 - 225,031; Full time

Benefits offered by this job

100% employer-paid medical insurance

Generous paid time-off policy

RSU stock grants

Professional development opportunities

Monthly cell phone stipend

Job summary

Fivetran is looking for a Regional Director, Enterprise Sales to lead and scale a team of high‑achieving Enterprise Account Executives. This role involves driving new business and expansion opportunities across strategic accounts in a full-time remote environment.

The ideal candidate will possess 5+ years of enterprise sales leadership experience and a proven track record of exceeding revenue goals. This position is ideal for a passionate leader looking to build a motivated team that excels in sales execution.

Qualifications

• 5+ years of experience in enterprise sales leadership.
• Proven history of exceeding revenue targets.
• Ability to foster trust among team members.

Responsibilities

• Attract and develop a team of Enterprise Account Executives.
• Drive a high-accountability culture through coaching.
• Collaborate cross-functionally to build effective GTM motion.

Skills

Enterprise sales leadership experience

Track record of recruiting high-performing AEs

Engaging with Economic Buyers

Ability to inspire and motivate teams

Expertise in outbound selling culture

Job description

Overview

Fivetran’s mission has remained the same: make access to data as simple and reliable as electricity.

About the Role

Fivetran is building data pipelines to power the modern data stack for thousands of companies. We’re looking for a Regional Director, Enterprise Sales to lead and scale a team of high‑achieving Enterprise Account Executives focused on driving new business and expansion opportunities across Fivetran’s most strategic accounts. This full‑time remote position is based in Minnesota, Michigan, Ohio, Wisconsin, or Illinois.

What You’ll Do

• Attract, hire, develop, and empower a team of Enterprise Account Executives to exceed Fivetran’s growing Enterprise revenue targets.
• Drive a high‑accountability culture through best‑in‑class coaching and disciplined sales process.
• Champion outstanding sales rigor through value‑based Command of the Message and MEDDPICC methodologies.
• Collaborate cross‑functionally with leaders in Marketing, Customer Success, Alliances, Product, and Revenue Operations to build an effective Enterprise GTM motion.
• Collaborate externally with our ecosystem of partners including SI’s, GSI’s, and tech partners.
• Ensure excellence in sales execution for complex multi‑stakeholder deals while building the foundation for growth in enterprise accounts.
• Drive AE‑ownership of Enterprise pipeline generation and encourage effective AE/BDR collaboration to prospect, qualify, and build sustainable pipeline.
• Forecast accurately to executive leadership and work with partners to achieve successful co‑selling.

Skills We’re Looking For

• 5+ years enterprise sales leadership experience with a track record of recruiting and retaining high‑performing senior AEs selling a technical solution to large, complex enterprises.
• Proven history of overachievement as an enterprise seller and as a leader whose teams consistently exceeded revenue targets.
• Ability to inspire and motivate AEs, fostering trust and a One Team One Dream mindset.
• Passion for field sales, capable of engaging directly with Economic Buyers and providing executive bridging to close new and expansion opportunities.
• Experience partnering cross‑functionally and co‑selling with external partners to build an Enterprise business from the ground up.
• Expertise in both land and expand sales motions and data‑backed vision for driving positive business outcomes.
• Experience building and championing an outbound selling culture and driving accountability for qualified pipeline generation.
• Unwillingness to settle for good results when great results are possible.

Bonus Skills

• Experience with a consumption business.
• Ability to leverage AI to enhance a richer, more robust sales motion.

Compensation

Pay Range: $180,025 — $225,031 USD
OTE (On Target Earning): $360,050 — $450,062 USD

Benefits

• 100% employer‑paid medical insurance
• Generous paid time‑off policy, paid sick time, parental leave, holidays, and volunteer days off
• RSU stock grants
• Professional development and training opportunities
• Company virtual happy hours, free food, and team‑building activities
• Monthly cell phone stipend
• Access to an innovative mental health support platform offering personalized care, coaching, and self‑guided mindfulness exercises for all covered employees and dependents.

EEO Statement

We are committed to ensuring that all candidates have an equal opportunity to participate in our interview process. If you require accommodations at any stage of the process due to a disability, medical condition, or any other circumstance, please submit your request. We will work with you to provide reasonable accommodations to facilitate your participation and ensure a fair and accessible interview experience. Your request and any information provided will be kept confidential and will not impact your candidacy.