Regional Director Sales, Boston (Enterprise)

Ladders; Boston (MA); Remote; USD 200,000 - 220,000; Full time

Benefits offered by this job

Health, dental, and vision insurance

Short-term disability and life 보험

Job summary

Ladders is seeking a Regional Director of Sales for the Boston area to lead an Enterprise sales organization in a remote-first environment. You will recruit and develop a 5-7 person team, build a strategic plan to exceed goals, and drive complex SaaS deals with Fortune 1000 customers across multiple time zones.

The role emphasizes leadership development, go-to-market execution, and maintaining high performance in a distributed setting. Remote work is core to this position.

Qualifications

• Minimum 5 years of leading Enterprise sales teams.
• Proven track record of annual overachievement.
• Experience with security channel partners.
• Familiarity with SaaS sales in cloud, logs, IT operations, and security.
• History of closing large deals with Fortune 1000 companies.
• Experience with MEDDIC methodology.

Responsibilities

• Recruit, develop, and lead a team of 5-7 Enterprise Sales Representatives
• Build a sales team and cultivate future sales leaders
• Develop a strategic business plan to exceed sales goals
• Manage the entire sales ecosystem from lead generation to closing
• Collaborate with a proven leadership team to shape the go-to-market strategy
• Adapt to a remote-first work environment across multiple time zones
• Occasionally perform duties outside standard working hours

Skills

Enterprise sales leadership

Team development

Pipeline development

SaaS sales

Complex deals

MEDDIC methodology

Tools

MEDDIC methodology

Job description

For our client, we are seeking a Regional Director Sales, Boston (Enterprise) to join the team of a leader in the Information Technology space.
This role will lead an Enterprise sales organization responsible for driving revenue growth in a remote-first environment. The position will focus on building a high-performing team, developing pipeline, and advancing complex sales cycles with large customers. You will partner closely with senior leadership to shape go-to-market strategy and strengthen market execution across multiple time zones.
The ideal candidate will bring deep enterprise sales leadership experience, a strong record of overachievement, and the ability to develop future sales leaders while consistently exceeding goals.
Location: Remote
Compensation: $200,000 – $220,000 annually

Responsibilities

• Recruit, develop, and lead a team of 5-7 Enterprise Sales Representatives
• Build a sales team and cultivate future sales leaders
• Develop a strategic business plan to exceed sales goals
• Manage the entire sales ecosystem from lead generation to closing
• Collaborate with a proven leadership team to shape the go-to-market strategy
• Adapt to a remote-first work environment across multiple time zones
• Occasionally perform duties outside standard working hours

Qualifications

• Minimum 5 years of leading Enterprise sales teams
• Proven track record of annual overachievement
• Experience leading sales teams selling through security channel partners
• Skilled in navigating complex sales cycles
• Familiarity with SaaS sales in cloud, logs, metrics, IT operations, and security
• History of closing large deals with Fortune 1000 companies
• Experience with MEDDIC methodology
• Proven ability to develop pipeline and open new accounts
• Preferred background in Cloud, Security, or Machine Learning

Benefits

• Health, dental, and vision insurance
• Short-term disability and life insurance
• Paid holidays and paid time off
• Fertility treatment benefit
• 401(k) plan
• Equity options
• Participation in the corporate bonus program

Our client is an equal opportunity employer. We encourage you to apply even if you don’t meet every qualification—your background could be exactly what this team needs.