VP, Biller Commercial Services (Inside Sales)

We are seeking an experienced and results-driven Vice President of Biller Commercial Services to lead our biller enrollment and retention strategies. In this senior leadership role, you will be responsible for developing and optimizing sales strategies that drive biller enrollment, improve retention rates, and reduce cancellations. You will oversee our Sales & Support teams, including Enrollment and Support, ensuring seamless, efficient, and digitally enhanced processes that maximize impact. 

The ideal candidate will have a proven track record in biller enrollment, multi-channel sales, and call center management in a fintech or similar high-tech environment. This role requires a strategic, hands-on leader with experience in optimizing sales processes, utilizing data insights, and leveraging new technology to enhance team performance and customer experiences. The successful candidate will be a strong coach, capable of leading large teams, driving performance, and improving customer outcomes. 

Key Responsibilities 

Biller Enrollment Strategy & Execution: 

• Lead the development and execution of a standardized sales strategy for biller enrollment, aligned with the company's broader goals. 

• Drive improvements in sales conversion, focusing on upselling, long-term retention, and expanding the value of customer relationships. 

• Streamline biller enrollment processes, reducing friction and enhancing the customer journey. 

• Build and optimize digital acquisition channels and selling/support automation to increase sales conversion and reduce customer acquisition cost (CAC). 

• Discover and optimize the acquisition channel mix in collaboration with marketing and Go-To-Market (GTM) Leader  

Retention & Cancellation Prevention: 

• Redefine and evolve customer support into a strategic function that not only drives retention but fuels product innovation, improves support efficiency, and develops a strong talent bench. 

• Design and implement strategies to proactively prevent cancellations, identify at-risk billers, and improve retention efforts. 

• Oversee the Support team in creating retention campaigns, proactive outreach initiatives, and personalized solutions aimed at reducing churn. 

• Standardize procedures for managing at-risk accounts and cancellations, ensuring consistent and effective communication. 

Team Leadership & Development: 

• Lead, manage, and mentor the Enrollment & Support teams (30-50+ people), including inside sales and call center functions, driving high performance and efficiency. 

• Foster a culture of accountability, collaboration, and continuous improvement, with a focus on achieving KPIs for sales, retention, and customer satisfaction. 

• Develop and implement effective sales training programs and ensure the team is well-equipped with the knowledge and skills needed to succeed in biller enrollment, retention, and product offerings. 

Process Standardization & Digitalization: 

• Standardize sales and support processes to ensure consistency, scalability, and an optimized customer experience. 

• Identify opportunities to digitize, automate, and improve key processes, enhancing team efficiency, speed, and accuracy. 

• Collaborate with the Technology team to integrate digital tools into workflows, improving operational performance and reducing manual tasks. 

Data-Driven Decision Making: 

• Analyze sales and retention data to identify trends, gaps, and opportunities for improvement. 

• Use performance metrics and data insights to inform strategic decisions and evaluate the effectiveness of sales and retention initiatives. 

• Provide regular performance reports to the executive team on sales results, retention metrics, and process improvements. 

Cross-Functional Collaboration: 

• Collaborate closely with Marketing and the Go-To-Market (GTM) Leader to ensure alignment across acquisition strategies, customer experience, and the packaging and promotion of payment solutions.  

• Partner with Marketing and GTM Leader to support SMB-focused initiatives, including input on demand generation efforts and solution packaging. 

• Collaborate with Marketing, Product, and Customer Success teams to align sales strategies with broader company goals and ensure seamless onboarding and customer experiences. 

• Serve as a strategic partner and advisor to senior leadership, offering insights and recommendations on sales and support-related matters. 

Executive Competencies: 

• Strong executive presence with a strategic mindset and business-first approach. 

• Proven ability to influence and align cross-functional stakeholders, including executive-level peers. 

• Comfortable presenting and selling ideas, strategies, and initiatives across the organization. 

• Brings a customer-centric lens to leadership and decision-making. 

Minimum Qualifications 

• Bachelor’s degree in business administration, sales, marketing, or a related field (MBA preferred). 

• Proven experience (10+ years) in a senior sales leadership role within fintech, financial services, wireless telecom, insurance, or business processing outsourcing (BPO), with a focus on enrollment, retention, and inside sales.

• Expertise in Direct to Business (D2B) sales, enrollment processes, sales for high-value products (e.g., >$500 annual revenue per lead), and support best practices. 

• Strong experience managing large inside sales teams 

• Demonstrated direct or indirect management of GTM payment solution packaging for SMB and demand generation. 

• Strong customer-driven mindset with experience in identifying and launching new solutions that add customer value and drive growth. 

• Demonstrated success in leading multi-channel sales strategies that integrate outbound calling, digital marketing (push & pull), and brand awareness marketing. 

• Experience in standardizing processes, driving digital transformation, and using technology to improve sales and support efficiencies. 

• Proven track record in hiring, training, coaching, and developing teams for high performance, including building succession plans. 

• Strong understanding of data analytics, lead targeting, and utilizing technological tools to drive performance and improve team effectiveness. 

• Experience with CRM systems (Salesforce, etc.), sales automation tools, and customer support platforms. 

• Excellent leadership, communication, and interpersonal skills, with the ability to inspire and motivate teams at all levels. 

SUPERVISORY RESPONSIBILITIES 

This position has direct and indirect supervisory responsibilities of a team of 40+ employees.