Vice President, Client Enrollments

Job Description

At Freedom Debt Relief, we help everyday people move from struggling to thriving with personalized financial solutions. We are evolving from a fully phone-led enrollment model to a digital-first, hybrid one. Clients can choose to enroll online with guided, AI-assisted help and work with a skilled advisor whenever that serves them better.

As Vice President, Client Enrollments, you will lead that transformation while meeting enrollment targets through it. You will own one enrollment funnel that leverages both modes, digital self-enrollment and agent-assisted sales, so they reinforce each other rather than compete. You will lead a multi-site and remote organization of directors, managers and hundreds of enrollment specialists.

This role collaborates with performance marketing, digital product, data science and the contact center systems. You own conversion yield, unit economics, contact strategy, regulatory compliance and, ultimately, achieving the enrollment targets committed to monthly, quarterly and annually. If you have led a sales organization through a shift like this, and grown the business in both modes at once, we want to talk to you.

What you'll do:

• Lead the hybrid enrollment transformation. Define and execute the roadmap from phone-led to digital-first enrollment. Set milestones for digital enrollment share, conversion and cost per enrollment, and sequence the change so enrollments grow throughout it.
• Shape the digital enrollment experience with Product. Partner with Product, Design and Engineering on the guided flow: discovery, solutioning, approval and enrollment. Define the milestones, when a human or AI agent steps in, and handoffs that give the advisor full context so the live conversation picks up where the member left off digitally.
• Redesign the sales operating model. Rethink how human and AI capacity is organized as more members enroll digitally. Refine team structures, lead ownership, compensation and incentives, and how work is routed. Build staffing and capacity plans that keep top talent engaged as roles evolve.
• Run a modern, multichannel contact strategy. Optimize for answer rate and trust, not dial volume. Lead branded calling, verified caller ID, SMS, email, chat and appointment scheduling, and protect line health and deliverability across carriers and devices.
• Engage the lead. Align preview, power and AI dialing to lead value, and build blended teams that work their pipeline, take new leads, and handle inbound calls and warm transfers.
• Put AI to work across the sales lifecycle. Deploy AI to deliver information to the advisors that will improve the consumer experience and strengthen the advisor’s performance.
• Measure everything and test rigorously. Establish KPIs from connect rate, connect-to-close, cost per enrollment, CAC and LTV. Use controlled tests and holdouts so changes such as new dialing strategies are measured and proven out, not assumed to be valuable.
• Drive enterprise alignment. Partner with Lending (personal loans and home equity) on shared assessment, lead-value scoring, a single consumer profile and cross-product pathing. Converge where it improves results and diverge deliberately where business needs and economics differ.
• Lead people through change. Reskill frontline teams for new roles, keep top talent through compensation and role changes, and build frontline leadership depth. Cultivate a culture anchored in Achieve's values: Care, Get Better, Act with Integrity and Collaborate.
• Champion compliance in every channel. With Legal, Risk and Compliance, maintain adherence to TSR, TCPA, FTC guidance, state debt relief laws and UDAAP. Extend that rigor to digital disclosures, e-signature, consent for SMS, and AI-assisted conversations.

What success looks like:

Success is a growing enrollment business that has become genuinely hybrid. Members can start and finish an enrollment online and can reach a skilled advisor when that serves them better; ultimately, both paths should feel like one integrated experience. Enrollments grow throughout the shift, not only after it, against targets set with executive leadership.

Behind that client experience sits a stronger foundation: higher answer rates and healthier lines, an operating model and incentives built for hybrid enrollment, and AI that makes every advisor more effective. Cost per enrollment falls, lifetime value rises, and Debt Relief works in step with Lending to match each consumer to the right solution.

Qualifications

What you'll bring

• A transformation you led. You have led, not just supported, a sales or enrollment organization through a shift from phone-led to digital or hybrid enrollment at scale. You can show the before and after: digital share, conversion, CAC and headcount.
• Growth in both modes at once. A track record of growing digital and advisor assisted channels together, resolving channel conflict, and building compensation and roles so frontline teams embraced the shift.
• Executive leadership at scale. 12+ years of progressive sales, enrollment or customer acquisition leadership, including 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.
• Multichannel contact expertise. Deep experience with voice, SMS, email, chat and AI voice in high-volume environments. You understand caller-ID reputation, branded calling, carrier spam labeling, consent management and dialer strategy, and how they drive answer rates.
• Digital funnel fluency. You have partnered closely with product and engineering on conversion funnels, A/B testing and milestone analytics, and you can shape a digital experience, not just staff the phones behind it.
• AI in sales operations. Hands-on experience deploying AI agent assist, conversational AI, automated disposition or AI-driven quality assurance, with measurable results and sound guardrails.
• Contact center technology. Experience scaling modern stacks, including telephony (e.g., Five9, Genesys, Twilio), CRM (e.g., Salesforce), preview, power and AI dialers, and messaging platforms.
• Commercial and analytical rigor. Command of unit economics, CAC and LTV, lead scoring and routing, capacity planning and incentive design for hybrid models. Comfortable with experiment design and holdout testing.
• Regulatory depth. Strong knowledge of consumer financial services regulation, the Telemarketing Sales Rule, TCPA, UDAAP and call center governance, including how they apply to digital and AI-assisted interactions.
• Change leadership and empathy. Proven ability to bring large frontline teams through change, present strategy to the C-suite, and keep deep empathy for consumers facing financial hardship.
• Education. Bachelor's degree required; MBA is a plus factor.

Additional Information

Achieve well-being with:

• 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, as well as dedicated volunteer days
• Access to wellness support through Employee Assistance Program, Talkspace, and fitness discounts
• Up to $5,250 paid back to you on eligible education expenses
• Pet care discounts for your furry family members
• Financial support in times of hardship with our Achieve Care Fund
• A safe place to connect and a commitment to diversity and inclusion through our six employee resource groups

Note: We will be unable to facilitate H1-B Visa transfer or sponsorship, along with STEM-OPT Visa.

Work from home/hybrid:

We are proudly offering hybrid options in the San Francisco, CA and Phoenix, AZ metro markets. Hiring remotely in selected locations throughout PST, MST, CST.

Salary Range: $240,000 to $275,000 salary + bonus + benefits.

This information represents the expected salary range for this role. Should we decide to make an offer for employment, we'll consider your location, experience, and other job-related factors.

Join Achieve, change the future.

At Achieve, we’re changing millions of lives.
From the single parent trying to catch up on bills to the entrepreneur needing a loan for the next phase of growth, you’ll get to be a part of their journey to a better financial future. We’re proud to have over 3,000 employees in mostly hybrid and 100% remote roles across the United States with hubs in Arizona, California, and Texas. We are strategically growing our teams with more remote, work-from-home opportunities every day to better serve our members. A career at Achieve is more than a job—it’s a place where you can make a true impact, have a sense of belonging, establish a fulfilling career, and put your well-being first.

Attention Agencies & Search Firms: We do not accept unsolicited candidate resumes or profiles. Please do not reach out to anyone within Achieve to market your services or candidates. All inquiries should be directed to Talent Acquisition only. We reserve the right to hire any candidates sent unsolicited and will not pay any fees without a contract signed by Achieve’s Talent Acquisition leader.