VP of Sales

Position Overview

ASI is seeking an experienced Sales Director to lead, coach, and develop a team of new-business sales professionals serving the community-banking market. This is a true management opportunity for someone who has personally succeeded as a hunter and understands what it takes to create opportunities, build credibility, navigate long sales cycles, and close complex software deals.

What You’ll Do

• Manage, motivate, and develop a team of Saas sales professionals focused primarily on acquiring new community-bank customers.
• Establish a high-energy, accountable Saas sales culture built around disciplined prospecting and consistent pipeline creation.
• Coach representatives through live deals, discovery calls, presentations, objections, negotiations, and closing strategies.
• Conduct regular one-on-one coaching sessions, pipeline reviews, call reviews, and deal-strategy meetings.
• Identify individual development needs and create practical coaching plans that improve performance.
• Train the team on outbound prospecting, consultative selling, executive discovery, competitive positioning, and relationship-based selling.
• Help sales representatives become more confident and effective when engaging bank CEOs, presidents, COOs, CIOs, and board members.
• Set clear performance expectations and address performance issues promptly, directly, and fairly.
• Build executive-level relationships with prospective community-bank customers.
• Help the team develop territory plans, target-account strategies, and personalized outreach campaigns.
• Step into complex or stalled opportunities to identify obstacles and establish a clear path forward.
• Develop and maintain strong relationships with consultants and trusted advisors serving community banks.
• Bring an existing network of community-banking consultants, bank executives, industry influencers, and referral partners- particularly within the Midwest or Southeast.
• Position ASI as a trusted option when consultants are advising banks on core evaluations, technology modernization, or vendor selection.
• Create a consistent approach to identifying, developing, and managing referral relationships.
• Maintain regular communication with consultants and partners so ASI remains top of mind for relevant opportunities.
• Track consultant- and partner-sourced opportunities with the same discipline applied to direct sales.
• Represent ASI at community-banking conferences, association events, consultant meetings, and regional industry gatherings.

What We’re Looking For

• Demonstrated success as a new-business Saas hunter selling within banking technology, fintech, core banking, or financial software.
• Previous experience managing, coaching, or training a team of hunters.
• A proven ability to improve prospecting, pipeline creation, sales discipline, and closing performance.
• Experience selling Finance Software in complex, high-value solutions with long and non-linear sales cycles.
• Strong knowledge of the community-banking ecosystem and how community banks evaluate technology partners.
• Established relationships with community-bank executives, consultants, banking associations, referral partners, or industry influencers.
• Experience developing consultant and referral channels that generate qualified opportunities.
• Ability to coach through real deals - not simply manage activity metrics and forecasts.
• Executive presence and the ability to build trust with bank CEOs, presidents, COOs, CIOs, and board members.
• Strong command of discovery, qualification, negotiation, and consultative selling.
• Experience using Salesforce or a comparable CRM to manage pipeline activity and forecast performance.
• Willingness to travel approximately 20–25% for customer meetings, team activities, conferences, and industry events.
• Residence in the Midwest or Southeast United States.

What ASI Offers

• Competitive base salary with performance-driven incentive compensation
• Unlimited PTO
• Standard company holidays
• Comprehensive health benefits
• 401(k) program
• Remote-first work environment
• Approximately 20–25% travel
• Opportunity to lead and develop a team in a growing, relationship-driven market
• Support from an established community-banking technology company with more than 40 years of experience
• A high-growth, PE-backed environment with meaningful career potential
• The opportunity to strengthen community banks and the communities they serve