VP of Sales - ASI

About the role

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.

Responsibilities

• 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.
• Create a consistent approach to identifying, developing, and managing referral relationships.
• 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.

Requirements

• 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.

Qualifications

• Education: Bachelor's degree preferred, but not required.
• Experience: Minimum 8 years of experience in sales, preferably in the banking technology sector.
• Technical Knowledge: Familiarity with banking technologies and software solutions is beneficial.

Skills

• Outbound prospecting skills.
• Consultative selling techniques.
• Executive-level communication and presentation skills.
• Strong organizational and time management skills.
• Ability to build and maintain relationships with key stakeholders.
• Experience with CRM systems.

Benefits

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
Opportunity to strengthen community banks and the communities they serve
Compensation: $130K to $150K USD Annual Base Salary (Uncapped commission)

Pay

$130K to $150K USD Annual Base Salary (Uncapped commission)

Schedule

Remote-first work environment with approximately 20–25% travel