Head of Software Sales and Customer Success

About iBusiness.ai

iBusiness.ai is a leading financial technology company helping banks, credit unions, and lenders modernize lending operations through secure AI, automation, and enterprise software. In the last decade the company's platforms have grown into supporting more than 50 financial institutions and have facilitated over $11 billion in lending volume.

As a pioneer in secure AI, automation, and AI software development, we build infrastructure and platforms that empower teams to modernize processes and work more efficiently without sacrificing compliance or security. Our workflow, verticalized, and point solutions enable seamless digital transformation, giving organizations of all sizes the tools they need to compete, innovate, and grow. 

Join us and be part of a team that’s building solutions designed to help businesses thrive!

Position Summary

iBusiness.ai is seeking an accomplished, commercially driven, technically fluent, and execution focused Head of Software Sales and Customer Success to lead the growth and performance of the Company’s software business.

This senior leadership role will oversee software sales, customer success, commercial execution, product commercialization, and customer growth. The ideal candidate will bring enterprise software sales leadership, customer success experience, financial services technology knowledge, operational discipline, and strong executive presence.

This person should be able to lead teams, improve commercial performance, support strategic customer relationships, represent the Company in the market, and help scale a high performing software business.

Major Areas of Responsibility

Sales and Revenue Leadership

• Lead software sales strategy and execution across the Company’s platforms, AI capabilities, automation solutions, and related products. Drive revenue growth through pipeline development, enterprise sales execution, account strategy, renewals, expansion, and customer growth.

Customer Success and Account Growth

• Lead customer success strategy focused on adoption, retention, renewals, customer value, and long term account growth. Build strong customer relationships and ensure customers realize measurable value from the Company’s software and services.

Commercial Operating Discipline

• Strengthen the systems, processes, and operating rhythms needed to manage a high performing commercial organization. Improve visibility, accountability, forecasting, pipeline quality, team execution, and overall commercial performance.

Team Leadership and Performance Management

• Lead, coach, and develop sales and customer success team members at different experience levels. Establish clear expectations, success metrics, development plans, and performance standards for both new and experienced team members.

Product Commercialization

• Support the launch and growth of the Company’s software platforms, AI capabilities, automation solutions, and new products. Partner across teams to align product readiness, customer needs, market feedback, messaging, enablement, and revenue goals.

AI and Product Evangelism

• Represent the Company as a market facing voice for its AI capabilities, software platforms, automation solutions, and new products. Participate in customer meetings, executive briefings, conferences, webinars, panels, partner discussions, and industry events.

Sales Enablement and Market Messaging

• Help strengthen sales messaging, customer communications, presentations, demo strategy, competitive positioning, and sales enablement. Ensure teams can clearly communicate the Company’s value to executive, technical, operational, and financial services stakeholders.

Pricing, Packaging, and Market Feedback

• Provide market informed input on pricing, packaging, positioning, customer needs, competitive trends, and revenue opportunities. Help translate market feedback into practical recommendations that support growth and customer value.

Cross Functional Leadership

• Partner with Sales, Customer Success, Product, Technology, Marketing, Operations, and Executive leadership to align priorities and drive execution. Help ensure customer needs, product direction, market feedback, and revenue goals are connected across the organization.

Required Knowledge, Skills, and Abilities

• 8 to 12 or more years of experience in enterprise software sales, customer success, commercial leadership, revenue leadership, business development, or related roles.
• Experience leading sales and customer success teams in B2B SaaS, fintech, financial services technology, lending technology, AI, automation, or related enterprise software environments.
• Proven ability to grow software revenue, improve sales performance, strengthen customer adoption, and build scalable commercial processes.
• Experience selling to or supporting banks, credit unions, lenders, fintech companies, or other regulated financial institutions strongly preferred.
• Strong understanding of enterprise sales cycles, including discovery, stakeholder management, business case development, negotiation, implementation alignment, and executive relationship management.
• Technical fluency with SaaS platforms, lending technology, workflow automation, integrations, data, AI capabilities, and software platforms.
• Ability to translate technology capabilities into clear business value for executive, technical, operational, and financial services stakeholders.
• Strong executive presence, communication skills, presentation ability, writing ability, and cross functional influence.
• Experience representing a company externally in customer meetings, executive briefings, conferences, panels, webinars, industry events, or partner discussions.
• Highly operational, accountable, and comfortable turning strategy into practical execution.
• Bachelor’s degree in business, finance, marketing, technology, or a related field required. MBA or relevant advanced degree preferred.

Preferred Qualifications

• Experience in lending, banking, fintech, financial services, loan origination, credit workflows, banking operations, or financial institution modernization.
• Experience commercializing new software products, automation solutions, workflow platforms, AI capabilities, or enterprise software platforms.
• Experience leading a sales or customer success organization through product launch, market repositioning, operational improvement, transformation, or growth.
• Strong network across banks, credit unions, fintech companies, lenders, financial institutions, industry associations, technology partners, or strategic partners.
• Experience with account based marketing, strategic partnerships, enterprise SaaS pricing, platform sales, renewals, expansion, sales compensation, customer success operations, or sales enablement.
• Experience developing thought leadership, conference presentations, webinars, industry content, product launch messaging, executive briefing materials, or customer education content.

Success Measures

The successful candidate will be expected to drive measurable improvement in software revenue growth, pipeline quality, sales execution, customer adoption, retention, renewals, expansion, forecasting accuracy, team performance, customer success outcomes, executive client relationships, and external market presence.

Success will also be measured by the candidate’s ability to strengthen commercial discipline, improve team performance, support new product commercialization, increase market visibility for the Company’s AI and software capabilities, and align cross functional teams around shared growth priorities.

Ideal Candidate Profile

The ideal candidate is a commercially driven software sales and customer success leader who can turn strategy into execution, customer relationships into growth, and team activity into measurable results.

This person is a builder, operator, coach, communicator, and public representative who can lead teams, strengthen customer relationships, support product growth, and help the Company win in a competitive market.