Vice President, Client Enrollments

This is a fully remote position, open to applicants in Illinois.

📋 Description

• Spearhead the transition from a phone-led approach to a digital-first, hybrid client enrollment model.

• Manage the comprehensive digital self-enrollment and agent-assisted enrollment funnel.

• Oversee a geographically diverse and remote team consisting of directors, managers, and numerous enrollment specialists.

• Establish key milestones for digital enrollment share, conversion rates, and cost per enrollment.

• Collaborate with Product, Design, and Engineering to create guided digital enrollment experiences.

• Define the handoff processes between humans and AI to maintain member context.

• Redesign sales operational frameworks, team structures, lead ownership, compensation models, incentives, and workflow routing.

• Develop staffing and capacity plans to meet organizational needs.

• Lead multi-channel contact strategies encompassing branded calling, verified caller ID, SMS, email, chat, and appointment scheduling.

• Enhance dialing efficiency, answer rates, trust, line health, and deliverability.

• Implement AI throughout the sales lifecycle to boost outcomes for both advisors and consumers.

• Set and track KPIs such as connect rate, connect-to-close ratio, cost per enrollment, customer acquisition cost (CAC), and lifetime value (LTV).

• Conduct controlled experiments and holdouts to assess the impact of strategies.

• Collaborate with the Lending team on assessments, lead-value scoring, consumer profiling, and cross-product pathing.

• Reskill frontline teams, retain valuable talent, and develop leadership capabilities.

• Ensure compliance with TSR, TCPA, FTC guidelines, state debt relief laws, UDAAP, digital disclosure requirements, e-signature protocols, SMS consent, and AI-assisted interactions.

⛳️ Requirements

• Bachelor's degree is mandatory; an MBA is considered an advantage.

• A minimum of 12 years in progressive sales, enrollment, or customer acquisition leadership roles.

• At least 5 years as a Senior Director or VP overseeing teams of 100 or more FTEs.

• Background in fintech, consumer lending, mortgage, insurance, debt relief, or comparable high-volume consumer sectors.

• Proven experience leading a sales or enrollment organization through a transition from phone-led to digital or hybrid enrollment on a large scale.

• Demonstrated success in expanding both digital and advisor-assisted channels simultaneously.

• Extensive experience with voice, SMS, email, chat, and AI voice in high-volume settings.

• Familiarity with caller-ID reputation, branded calling, carrier spam labeling, consent management, and dialing strategies.

• Proficient in digital conversion funnels, A/B testing, and milestone analytics.

• Practical experience deploying AI agent assist, conversational AI, automated disposition, or AI-driven quality assurance.

• Experience in scaling telephony, CRM systems, dialers, and messaging platforms, including Five9, Genesys, Twilio, and Salesforce.

• Strong understanding of unit economics, CAC, LTV, lead scoring, routing, capacity planning, and incentive design.

• Experience in experimental design and holdout testing methodologies.

• In-depth knowledge of TSR, TCPA, UDAAP, regulations in consumer financial services, and call center governance.

• Proven ability in change leadership, strategy presentation to C-suite executives, and empathy towards consumers experiencing financial difficulties.

• Must have authorization to work in the United States; H1-B Visa transfer/sponsorship and STEM-OPT Visa cannot be accommodated.

🏝️ Benefits

• Opportunities for hybrid and remote work.

• 401(k) plan with employer matching contributions.

• Comprehensive medical, dental, and vision coverage, including HSA and FSA options.

• Competitive vacation and sick leave policies.

• Designated volunteer days.

• Employee Assistance Program.

• Access to Talkspace.

• Discounts on fitness memberships.

• Up to $5,250 reimbursement for eligible educational expenses.

• Discounts on pet care services.

• Financial support through the Achieve Care Fund.

• Six active employee resource groups.

• Bonus compensation opportunities.