VP, Hybrid Enrollment & Digital Growth

Achieve; Chicago (IL); Hybrid; USD 240,000 - 275,000; Full time

Benefits offered by this job

Hybrid/Remote work opportunities

401(k) matching

Medical, dental, vision

Job summary

Achieve is seeking a Vice President, Client Enrollments to lead a major transformation from phone-led enrollment to a digital‑first, hybrid model. You will own a unified enrollment funnel across digital self‑enrollment and advisor‑assisted channels, guiding a multi‑site and remote organization of directors, managers, and hundreds of enrollment specialists.

You will collaborate with performance marketing, digital product, data science, and contact center systems to optimize conversion, unit

Qualifications

• 12+ years of progressive sales/enrollment leadership.
• 5+ years as Senior Director or VP leading 100+ FTEs.
• Experience in fintech, consumer lending, mortgage, debt relief or similar high‑volume consumer businesses.
• Deep experience with voice, SMS, email, chat and AI voice in high‑volume environments.
• Partnership with product and engineering on conversion funnels, A/B testing and analytics.
• Hands-on with AI agent assist, conversational AI or AI-driven quality assurance.

Responsibilities

• Lead the hybrid enrollment transformation from phone-led to digital-first enrollment.
• Shape the digital enrollment experience with Product, Design and Engineering.
• Redesign the sales operating model and staffing plans.
• Run a modern, multichannel contact strategy across channels.
• Engage the lead and align AI dialing to lead value.
• Put AI to work across the sales lifecycle to improve advisor performance.
• Measure KPIs and run controlled tests for optimization.
• Drive enterprise alignment with Lending and cross‑product pathing.
• Lead change, reskill teams, and uphold Achieve’s values.

Skills

Transformation leadership

Executive leadership

Multichannel contact

Digital funnel

AI in sales

Regulatory knowledge

Change management

Growth strategy

Leadership at scale

Communication skills

Education

Bachelor's degree

MBA (plus)

Tools

Five9

Genesys

Twilio

Salesforce

Job description

Achieve is seeking a Vice President, Client Enrollments to lead a major transformation from phone-led enrollment to a digital‑first, hybrid model. You will own a unified enrollment funnel across digital self‑enrollment and advisor‑assisted channels, guiding a multi‑site and remote organization of directors, managers, and hundreds of enrollment specialists.

You will collaborate with performance marketing, digital product, data science, and contact center systems to optimize conversion, unit