Regional Director, Enterprise

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

WFA Digital Insight

The demand for skilled sales leaders in the tech industry has grown significantly, with a 25% increase in remote job postings in 2025. As companies like Fivetran continue to expand their enterprise sales teams, the need for experienced professionals with a deep understanding of GTM and data analysis has never been more pressing. With Fivetran's mission to simplify data access, this role offers a unique opportunity to lead a high-performing team and drive business growth. Candidates should be prepared to showcase their ability to drive sales excellence, collaborate with cross-functional teams, and leverage their technical expertise to drive results.

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 will focus on driving new business and expansion opportunities across Fivetran's most strategic accounts. As a foundational leader in the Enterprise business, the successful candidate will report directly to the RVP of Enterprise Sales and will be responsible for driving revenue growth, developing and executing sales strategies, and collaborating with cross-functional teams to build an effective Enterprise GTM motion.

The ideal candidate will have a deep understanding of the sales process, exceptional leadership skills, and a proven track record of driving sales excellence in a fast-paced, dynamic environment. They will be responsible for attracting, hiring, and developing a team of talented Enterprise Account Executives, and will work closely with the sales operations team to ensure seamless sales execution.

Fivetran is committed to making access to data as simple and reliable as electricity. With a strong focus on innovation and customer satisfaction, the company is poised for continued growth and success. As a Regional Director, Enterprise Sales, you will be at the forefront of this growth, driving business expansion and developing strategic partnerships to propel the company forward.

What You Will Do

  • Attract, hire, and develop a team of high-performing Enterprise Account Executives to drive revenue growth and expansion
  • Drive a high-accountability culture through best-in-class coaching, clear expectations, and a disciplined process for the team
  • Collaborate with cross-functional teams, including Marketing, Customer Success, Alliances, Product, and Revenue Operations to build an effective Enterprise GTM motion
  • Champion outstanding sales rigor through value-based Command of the Message and MEDDPICC methodologies
  • Ensure excellence in sales execution for complex multi-stakeholder deals, 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
  • Develop and execute sales strategies to drive revenue growth and expansion
  • Collaborate with the sales operations team to ensure seamless sales execution

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
  • Natural ability to lead and develop high-performing teams, with a strong focus on coaching, mentoring, and sales excellence
  • Strong understanding of GTM and data analysis, with the ability to leverage technical expertise to drive sales results
  • Excellent communication, interpersonal, and problem-solving skills, with the ability to collaborate effectively with cross-functional teams and partners
  • Strong business acumen, with the ability to drive revenue growth and expansion through strategic planning and execution
  • Experience working in a fast-paced, dynamic environment, with a strong ability to adapt to changing circumstances and priorities

Nice to Have

  • Experience working with data analysis tools and technologies, such as Excel, SQL, and data visualization software
  • Knowledge of sales methodologies, such as Command of the Message and MEDDPICC
  • Experience working in a remote or distributed team environment, with a strong ability to collaborate and communicate effectively with team members and stakeholders
  • Certification in sales or a related field, such as CSO or CSS

Benefits and Perks

  • Competitive salary and bonus structure, with a strong focus on performance-based rewards
  • Comprehensive benefits package, including health, dental, and vision insurance, as well as a 401(k) matching program
  • Flexible work arrangements, including remote work options and a flexible vacation policy
  • Opportunities for professional development and growth, including training, mentorship, and career advancement opportunities
  • Access to the latest tools and technologies, including data analysis software and sales enablement platforms
  • Collaborative and dynamic work environment, with a strong focus on teamwork, innovation, and customer satisfaction
  • Recognition and rewards for outstanding performance, including sales achievements and company-wide recognition programs
  • Equity and stock options, with the opportunity to participate in the company's growth and success

How to Stand Out

  • Develop a strong understanding of Fivetran's products and services, as well as the company's mission and values, to demonstrate your passion and commitment to the role.
  • Highlight your experience working with data analysis tools and technologies, such as Excel and SQL, to showcase your technical skills and expertise.
  • Showcase your ability to drive sales excellence, including your experience with sales methodologies and your track record of achieving revenue targets and growing sales teams.
  • Be prepared to provide specific examples of your sales experience, including successful sales strategies and tactics, and your ability to collaborate with cross-functional teams and partners.
  • Research the company culture and values, and be prepared to discuss how you align with Fivetran's mission and values, and how you can contribute to the company's growth and success.
  • Practice your sales pitch and be prepared to articulate your value proposition, including your unique skills and experience, and how you can drive revenue growth and expansion for Fivetran.

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