Vice President, Client Enrollments

Achieve

. Lead the transformation from phone-led to digital-first, hybrid client enrollment .

Posted 11/3/2026full-timeRemote • Chicago • Illinois • United StatesLead💰 $240,000 - $275,000 per yearWebsite

Core Competencies

Role fit

Core Competencies

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Demonstrates expertise in leading digital transformation initiatives in enrollment processes, with a strong focus on optimizing multichannel strategies and deploying AI solutions to enhance consumer outcomes. Proven ability to manage large teams and drive compliance with financial regulations while achieving key performance indicators.

Highest-signal resume keywords

Digital Enrollment LeadershipAI Deployment in SalesMultichannel Contact StrategyCompliance with Financial RegulationsChange Leadership

ATS Keywords

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Applicant Tracking System Keywords

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Hard Skills

Digital Conversion FunnelsA/B TestingUnit EconomicsLead ScoringCapacity PlanningIncentive DesignSales Funnel OptimizationKPI EstablishmentExperiment DesignAnalytics

Soft Skills

Empathy for ConsumersChange LeadershipC-Suite Strategy Presentation

Tools & Technologies

Five9GenesysTwilioSalesforceAI VoiceConversational AIAutomated DispositionDialer StrategyMessaging PlatformsCRM

Industry Keywords

FintechConsumer LendingMortgageInsuranceDebt ReliefHigh-Volume Consumer BusinessesTSRTCPAUDAAPConsumer Financial Services Regulation

About the role

Key responsibilities & impact

Lead the transformation from phone-led to digital-first, hybrid client enrollment
Own the integrated digital self-enrollment and agent-assisted enrollment funnel
Lead a multi-site and remote organization of directors, managers and hundreds of enrollment specialists
Set milestones for digital enrollment share, conversion and cost per enrollment
Shape guided digital enrollment experiences with Product, Design and Engineering
Define human and AI handoffs that preserve member context
Redesign sales operating models, team structures, lead ownership, compensation, incentives and work routing
Build staffing and capacity plans
Lead multichannel contact strategies across branded calling, verified caller ID, SMS, email, chat and appointment scheduling
Optimize dialing, answer rates, trust, line health and deliverability
Deploy AI across the sales lifecycle to improve advisor and consumer outcomes
Establish KPIs including connect rate, connect-to-close, cost per enrollment, CAC and LTV
Run controlled tests and holdouts to measure strategy impact
Partner with Lending on assessment, lead-value scoring, consumer profiles and cross-product pathing
Reskill frontline teams, retain talent and build leadership depth
Maintain compliance with TSR, TCPA, FTC guidance, state debt relief laws, UDAAP, digital disclosures, e-signature, SMS consent and AI-assisted conversations

Requirements

What you’ll need

Bachelor's degree required; MBA is a plus factor
12+ years of progressive sales, enrollment or customer acquisition leadership
5+ years as a Senior Director or VP leading 100+ FTEs
Experience in fintech, consumer lending, mortgage, insurance, debt relief or similar high-volume consumer businesses
Led a sales or enrollment organization through a shift from phone-led to digital or hybrid enrollment at scale
Track record of growing digital and advisor-assisted channels together
Deep experience with voice, SMS, email, chat and AI voice in high-volume environments
Knowledge of caller-ID reputation, branded calling, carrier spam labeling, consent management and dialer strategy
Experience with digital conversion funnels, A/B testing and milestone analytics
Hands-on experience deploying AI agent assist, conversational AI, automated disposition or AI-driven quality assurance
Experience scaling telephony, CRM, dialers and messaging platforms, including Five9, Genesys, Twilio and Salesforce
Command of unit economics, CAC, LTV, lead scoring, routing, capacity planning and incentive design
Experience with experiment design and holdout testing
Strong knowledge of TSR, TCPA, UDAAP, consumer financial services regulation and call center governance
Proven change leadership, C-suite strategy presentation and empathy for consumers facing financial hardship
Must be authorized to work in the United States; H1-B Visa transfer/sponsorship and STEM-OPT Visa cannot be facilitated

Benefits

Comp & perks

Hybrid and remote work opportunities
401(k) with employer match
Medical, dental, and vision with HSA and FSA options
Competitive vacation and sick time off
Dedicated volunteer days
Employee Assistance Program
Talkspace
Fitness discounts
Up to $5,250 paid back on eligible education expenses
Pet care discounts
Financial support through the Achieve Care Fund
Six employee resource groups
Bonus compensation