Regional Director, Enterprise

Fivetran·Remote(Remote, Minnesota, United States, AMER)
Software Development
GTMExcel

WFA Digital Insight

The demand for seasoned sales leaders in the tech industry has grown exponentially, with a 25% increase in remote job openings in 2025. As companies like Fivetran continue to expand their enterprise offerings, the need for strategic directors who can drive growth and revenue has become paramount. With the rise of data-driven decision-making, professionals with expertise in GTM and data analysis are in high demand. Fivetran's commitment to making data access simple and reliable has positioned the company for significant growth, and this role offers a unique opportunity for a sales leader to make a lasting impact. Before applying, candidates should be prepared to showcase their ability to scale high-performing teams and drive complex sales initiatives.

Job Description

About the Role

The Regional Director, Enterprise Sales will play a critical role in leading and scaling a team of high-achieving Enterprise Account Executives at Fivetran. This team is focused on driving new business and expansion opportunities across Fivetran's most strategic accounts. As a key leader in the Enterprise business, this role will report directly to the RVP of Enterprise Sales and will be instrumental in shaping the company's sales strategy.

The successful candidate will have a deep understanding of the enterprise sales landscape and a proven track record of recruiting, developing, and retaining high-performing sales teams. They will be responsible for driving a high-accountability culture, championing sales rigor, and collaborating with cross-functional teams to build an effective Enterprise GTM motion.

Fivetran's mission is to make access to data as simple and reliable as electricity, and the Regional Director, Enterprise Sales will be a key player in helping the company achieve this goal.

What You Will Do

  • Attract, hire, develop, and empower a team of Enterprise Account Executives to consistently and predictably exceed Fivetran's growing Enterprise revenue targets
  • Drive a high-accountability culture through best-in-class coaching, modeling clear expectations for achievement, and evangelizing a disciplined process for the team
  • 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 Fivetran's 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 efficiently prospect, identify, qualify, and build sustainable pipeline
  • Forecast clearly to the executive leadership team, with consistent accuracy and a deep knowledge of the Enterprise business
  • Work in lockstep with technology and SI partners to achieve a successful co-selling motion

What We Are Looking For

  • 5+ years of enterprise sales leadership experience with a consistent track record of recruiting and retaining high-performing senior AEs selling technical solutions to large, complex enterprises
  • Proven and repeatable history of overachievement both as an enterprise seller and a leader whose teams consistently exceeded revenue targets and accelerated their careers under your leadership
  • Natural ability to lead and manage high-performing teams, with a focus on coaching, development, and talent management
  • Strong understanding of the enterprise sales landscape, including the ability to navigate complex sales cycles and build strong relationships with key decision-makers
  • Excellent communication and interpersonal skills, with the ability to effectively collaborate with cross-functional teams and external partners
  • Strong analytical and problem-solving skills, with the ability to analyze complex data sets and develop strategic sales plans

Nice to Have

  • Experience with data analysis and visualization tools, such as Excel, Tableau, or Power BI
  • Knowledge of sales methodologies, such as Command of the Message and MEDDPICC
  • Experience working with CRM systems, such as Salesforce.com
  • Familiarity with the data integration and analytics market, including trends and key players

Benefits and Perks

  • Competitive salary and bonus structure
  • Equity package
  • Comprehensive health, dental, and vision insurance
  • 401(k) matching program
  • Flexible PTO policy
  • Remote work stipend
  • Professional development opportunities, including training and conference sponsorships
  • Access to a comprehensive suite of sales tools and technologies

How to Stand Out

  • Tip: Highlight your experience with GTM and data analysis in your resume and cover letter to stand out as a candidate.
  • Be prepared to discuss your sales methodology and how you have applied it in previous roles to drive revenue growth.
  • Showcasing your ability to build and manage high-performing teams will be critical in this role, so be prepared to provide specific examples.
  • Familiarize yourself with Fivetran's products and services, as well as the company's mission and values, to demonstrate your interest and enthusiasm for the role.
  • Consider creating a portfolio of your sales achievements and strategies to share with the interviewer.
  • Don't be afraid to ask questions about the company culture and team dynamics during the interview process.

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