VP, Mid-Market SaaS Sales (OTE $380k-$420k, 10+ Years SaaS Leadership Exp. Req.) REMOTE

twiceasnice Recruiting; Town of Texas (WI); Remote; USD 190,000 - 210,000; Full time

Job summary

A leading company in revenue orchestration software is seeking a Vice President of Mid-Market Sales to oversee a team and drive growth across North America. The ideal candidate will have extensive SaaS experience and a track record of success in management roles, helping to scale operations and sales strategies effectively.

Benefits

Medical

Dental

Vision

Disability

401K w/ Match

Unlimited PTO

Tuition Reimbursement

Qualifications

• 10+ years of proven management experience in SaaS.
• Experience across diverse SaaS customer segments, including B2B tech.
• Success leading mid-market teams selling to companies with 1,000+ employees.

Responsibilities

• Lead, scale & support a team of regional VPs & front-line managers across North America.
• Own the overall mid-market revenue strategy, including net-new acquisition and cross-sell.
• Actively coach & develop sales leaders while fostering a high-performance culture.

Skills

Management experience in SaaS environment

Operational strategy

P&L understanding

CRM & AI tools

Education

Bachelor’s degree

Job description

VP, Mid-Market SaaS Sales – North America (10+ Years Leadership Req.)
Location: Remote – United States
Salary: Base $190k-$210k + Uncapped Commission (OTE $380k-$420k) + Stock
Benefits: Medical, Dental, Vision, Disability, 401K w/ Match, Unlimited PTO, Tuition Reimbursement
Job Type: Full-Time
Start Date: ASAP
Sponsorship: Not available
Relocation Assistance: Not Available
Territory: North America
Travel: ~30% across North America (~3 nights every other week)

VP, Mid-Market SaaS Sales – North America (10+ Years Leadership Req.) Description

Our client, a global leader in revenue orchestration software, is seeking a hands-on Vice President of Mid-Market Sales to lead, develop, and directly support a high-performing sales organization across North America. This role oversees a team of Regional VPs and front-line managers, with full accountability for driving new logo acquisition, cross-selling expansion, and achieving aggressive revenue growth in the mid-market segment. The ideal candidate is a gritty, roll-up-your-sleeves sales executive with deep SaaS experience and a passion for building and scaling quickly. You must be comfortable staying close to the field, actively coaching managers, joining client conversations, and ensuring sales strategy translates into execution. This is a high-impact leadership opportunity to build a best-in-class sales engine in a fast-growing, high-performance environment.

VP, Mid-Market SaaS Sales – North America (10+ Years Leadership Req.) Responsibilities

• Lead, scale & support a team of regional VPs & front-line managers across North America
• Own the overall mid-market revenue strategy, including net-new acquisition and cross-sell
• Actively coach & develop sales leaders while fostering a high-performance, accountable culture
• Stay close to the field — join prospect calls, assist with deal strategy, and model best practices
• Define and implement sales playbooks and KPI frameworks
• Align cross-functionally to optimize go-to-market strategy
• Guide teams through complex sales cycles with structure, creativity, and urgency
• Oversee pipeline generation, forecasting, and territory planning across regions
• Champion the adoption of technology and analytics to improve sales efficiency and performance
• Represent Mid-Market Sales in strategic planning and executive-level discussions
• Build scalable programs for onboarding, enablement, and talent development
• Promote a team-first culture rooted in continuous learning, integrity, and customer focus

VP, Mid-Market SaaS Sales – North America (10+ Years Leadership Req.) Qualifications

• Bachelor’s degree is required
• 10+ years of proven management experience in SaaS environment is required
• Experience across diverse SaaS customer segments, including B2B tech is required
• Proven success leading mid-market teams selling to companies with 1,000+ employees
• Prior success scaling B2B sales in both small & large companies is required
• Strong operational strategy, P&L understanding, & continuous improvement is required
• Experience leveraging CRM & AI tools to drive sales performance is required