ASG VP of Sales

ASG • Newton, MA

8h • $260,000 - $300,000 • Hybrid

About The Position

ASG is an unconventional group of market-leading software companies, serving industries ranging from behavioral health to retail to hospitality. ASG believes deeply in the power of people and data to grow great organizations, and that sharing knowledge, expertise, and resources across its community of businesses drives exponential growth. ASG has acquired over 60 businesses since its inception in August of 2016. We are backed by Alpine Investors and operated by world-class PeopleFirstTM leaders. Founders of leading SaaS companies continue to trust ASG to grow their businesses and build even stronger legacies for the future. To learn more, visit www.alpinesg.com.
JOB DESCRIPTION
The VP, Sales designs and leads revenue acceleration initiatives across ASG’s portfolio of Operating Companies with a clear mandate: double bookings within 18 months by building repeatable, durable revenue engines. Reporting to the Chief GTM Officer, this leader partners directly with CEOs and sales leaders to professionalize and scale GTM functions, institutionalize best-in-class sales systems, and ensure new acquisitions are onboarded with rigor and velocity. This is both a strategic and hands-on role—requiring the ability to architect portfolio-wide playbooks while stepping into interim leadership when needed.

Requirements

• You have 10+ years of experience leading high-performing SaaS sales teams, with a track record of consistently exceeding bookings targets.
• You have built and scaled repeatable sales systems that improved pipeline coverage, forecast accuracy, and win rates in measurable ways.
• You have strong executive presence and experience coaching and influencing CEOs and senior leaders.
• You have successfully hired, developed, and upgraded A-player sales talent and leadership.
• You are fluent in SaaS metrics and operate from a rigorous, data-driven foundation.
• You have practical experience leveraging AI in sales or customer operations to improve forecasting, productivity, positioning, or support efficiency.
• You are comfortable operating in ambiguous or transitional environments and stepping into hands-on leadership when needed.
• You are willing and able to travel approximately 20% of the time.
• You strongly align with our cultural principles of “Will to win and win with love” and “Entrepreneurs at heart.”

Responsibilities

• Lead portfolio-wide sales engagements that drive measurable bookings growth and establish consistent performance standards.
• Refine and operationalize GTM playbooks to build repeatable revenue systems that create long-term enterprise value.
• Partner with CEOs to improve pipeline coverage, forecast accuracy, win rates, and sales productivity using rigorous SaaS metrics and operating cadence.
• Assess, hire, and upgrade sales leadership talent—ensuring the right leaders are in the right seats across the portfolio.
• Step into interim or fractional sales leadership roles to stabilize performance, evaluate teams, and accelerate results when needed.
• Serve as the GTM operating partner for new acquisitions—leading onboarding, revenue acceleration planning, systems implementation, and early talent evaluation.
• Institutionalize AI within GTM workflows to enhance forecasting accuracy, pipeline visibility, positioning, and operational leverage across sales and customer support.
• Strengthen RevOps foundations and measurement infrastructure to ensure accountability, visibility, and scalable growth across diverse SaaS businesses.

What This Job Offers

• Job Type: Full-time
• Career Level: Executive
• Education Level: No Education Listed