- VP of Client Success | AI SaaS
- Reports to CEO
- Automotive (Alpha Drive AI) & Luxury Hospitality (Call Stream AI)
- Remote (Florida) + Up to 25% Travel
- Full-Time | FLSA: Exempt
- Base $150,000–$175,000 |* OTE $185,000–$215,000 | *Equity eligible
The Opportunity
We are hiring our first VP of Client Success to own the entire post-sale experience across both of our AI divisions — Alpha Drive AI (automotive) and Call Stream AI (luxury hospitality). This is a build-and-lead role. You will own implementation of new clients, retention and growth of existing ones, and the client help desk — and you will build and train the team that delivers all of it.
You are a self-starter who shows up with a plan. We are not looking for someone to be told how client success works; we are looking for the operator who has stood up this function before and can do it again, faster, here. You will inherit a small team and a strong client base, and your job is to turn both into a scalable, repeatable, technically credible client success organization.
Our clients are sophisticated operators — dealer principals, General Managers, Fixed Ops Directors, hotel GMs, and F&B directors — who expect a peer, not a vendor, and who can tell the difference in the first five minutes of a call. If you can earn their trust, speak credibly about how the product actually works, and lead a team to do the same at scale, this role is built for you.
About Our Two Divisions
ALPHA DRIVE AI
Alpha Drive AI is the most customizable AI communication platform for automotive dealerships. We handle inbound and outbound calls, lead capture, scheduling, and BDC functions 24 hours a day, helping dealers book more appointments and capture more leads without adding headcount. As featured on CBT News. Our clients are competitive, ROI-driven, and protective of their customer relationships.
CALL STREAM AI
Call Stream AI powers the full guest economy — hotels, restaurants, venues, travel, and beyond. We serve Michelin-starred restaurants, Forbes Five-Star hotels, Michelin Key properties, Conde Nast award winners, and World Travel Award recipients. Our AI handles reservations, guest inquiries, upsells, and follow-up automatically. Our clients here run properties where brand reputation and guest experience are everything, and they expect excellence from every vendor.
What You Will Do
-- Lead the Client Success Organization
- Own the full post-sale client lifecycle — implementation, retention, growth, and support — across both Alpha Drive AI and Call Stream AI
- Set the strategy, standards, playbooks, and metrics for the client success function and own its results
- Serve as the senior client-facing leader for our most important and most sophisticated accounts
- Report directly to the CEO and act as the voice of the client at the leadership table
-- Implementation & Onboarding
- Own implementation of new clients from signed contract through live deployment across both divisions
- Project-manage technical setup, AI voice configuration, system integrations, and staff training
- Build and continuously refine the implementation playbook so launches are repeatable, clean, and on time
- Partner with product and engineering to clear technical blockers and ensure every go-live lands
-- Retention, Renewals & Growth
- Own net revenue retention and churn across the entire client base
- Build proactive account-health monitoring — usage data, response rates, satisfaction signals — and an early-warning system for at-risk accounts
- Personally lead recovery on escalations and high-value at-risk accounts where senior involvement is warranted
- Own renewal and expansion strategy, and equip the team to grow accounts, not just maintain them
-- Help Desk & Support Operations
- Own the client help desk — staffing, processes, escalation paths, SLAs, and quality
- Define response and resolution targets, hit them, and build the reporting that proves it
- Turn recurring support themes into product feedback and process improvement
-- Systems & Tooling Ownership
- Architect and own the client function’s tech stack — HubSpot, Jira, and ClickUp — at an advanced, hands-on level
- Build out CRM pipelines, ticketing and escalation workflows, implementation boards, automations, dashboards, and reporting; don’t just operate the tools, design how the team works inside them
- Understand our AI voice platform (e.g., Bland AI) conceptually — call flows, pathways, prompts — well enough to direct and support the team configuring it
- Standardize and document the operational tooling so the function scales cleanly as the team grows
-- Team Building & Enablement
- Recruit, hire, and onboard the client success and implementation team
- Train and level up the people already in place — including the Client Experience Managers — on product depth, client handling, and operational rigor
- Establish onboarding, ongoing enablement, and a culture of consultative, technically fluent client engagement
-- Voice of the Client & Cross-Functional Leadership
- Partner with the Chief Product Officer on client-informed product priorities
- Represent the client perspective in leadership decisions on roadmap and go-to-market
- Surface product gaps and market insight from the front line of both industries
What We Are Looking For
- 7+ years in SaaS client success, account management, or implementation, including 3+ years building and leading a team
- Proven experience standing up or scaling a client success, implementation, or support function — not just running one that already exists
- Direct experience in, or selling into, automotive (dealerships, OEM, dealer technology), call centers / BDC, and/or luxury hospitality is strongly preferred
- Hands-on implementation experience — you have project-managed software go-lives at customer sites
- Comfortable owning a help desk or support operation with defined SLAs
- Advanced, hands-on administrator of HubSpot, Jira, and ClickUp — you don’t just use these systems, you build them out: pipelines, workflows, automations, boards, dashboards, and reporting
- Able to design and own the operational tooling for the whole client function — ticketing, onboarding workflows, and account-health reporting — and train the team to run inside it
- Conceptual understanding of conversational AI voice platforms (e.g., Bland AI) — enough to speak credibly to how call flows, pathways, and prompts work and to partner with the team configuring them
- Technical fluency — you can hold a credible, detailed conversation about how the product actually works with a sophisticated operator, without retreating to a script
- A self-starter who arrives with a plan; you have built from zero before
- Executive presence and consultative credibility with senior dealer principals, GMs, Fixed Ops Directors, hotel GMs, and F&B directors
- Genuinely fluent with modern AI tools (Claude, ChatGPT, Gemini) and with SaaS as a category
- Comfortable using data and metrics as the working language of the function
- Willing to travel up to 25%, and energized by learning both the automotive and hospitality worlds deeply and quickly
Compensation
We believe in being upfront about pay. This role offers a base salary of $150,000–$175,000 depending on experience, with on-target earnings (OTE) of $185,000-$215,000. This includes annual performance bonus tied to retention, implementation, and support targets. This role is eligible for equity / long-term incentive participation. Full compensation details are provided during the offer conversation.
Benefits
- Health, dental, vision and life insurance
- 401(k) matching
- Paid time off
- Remote work (FL) — approved home office environment
- Paid travel for client visits and team events
How to Apply
Submit your resume. Candidates with automotive, call center, or luxury hospitality experience are reviewed first. Optionally include a brief paragraph on a client success, implementation, or support function you built or scaled — and what made it work.
Work Environment
This position operates in a professional home office or approved remote work environment and routinely uses standard office equipment including computers, phones, and video conferencing tools. It requires extended periods of computer and phone use. Regular travel to client sites, team meetings, and industry events is required.
Systems and Tools
This is a hands-on, build-it-yourself role. Our client operations run on HubSpot (CRM, pipelines, and reporting), Jira (project and issue tracking), and ClickUp (work and implementation management), and we expect a VP who is advanced enough in all three to architect them — not just use them. You will design the pipelines, workflows, automations, boards, and dashboards the whole team works inside, and train the team to run there. Our AI products are built on a cascading LLM architecture across Anthropic Claude, OpenAI ChatGPT, and Google Gemini, with conversational voice handled through platforms like Bland AI; you should understand these conceptually and partner with the team configuring them. Hands-on fluency with modern AI assistants is expected, and day-to-day work also runs through Google Workspace and Slack.
Physical Demands
The physical demands described here are representative of those that must be met by an employee to successfully perform the essential functions of this job. While performing the duties of this job, the employee is regularly required to talk or hear. The employee frequently is required to sit, stand, walk, use hands to handle and feel, and reach with hands and arms. The employee must occasionally lift and/or move up to 25 pounds, such as marketing materials, product samples, or trade show materials. Ability to communicate effectively in person, via phone, and via video conferencing for extended periods is required. The employee must be comfortable with travel, including air travel, driving, and extended time away from the primary work location.
Position Type and Expected Hours of Work
This is a full-time position. Hours of work may vary and flexibility is required. Evening and weekend availability may occasionally be needed based on client time zones and urgent client needs.
Travel
Travel is required up to 25% of the time for client visits, onboarding or implementation sessions, team meetings in Estero, Florida, and industry events.
Other Duties
Please note this job description is not designed to cover or contain a comprehensive listing of activities, duties, or responsibilities required of the employee. Duties, responsibilities, and activities may change at any time with or without notice.
FLSA Status
Exempt
AAP/EEO STATEMENT
Dealer’s Greatest Assets d/b/a Alpha Drive AI LLC provides equal opportunity in employment for all qualified persons and prohibits discrimination in employment on the basis of race, color, religion, creed, sex, sexual orientation, gender identity, national origin, ancestry, age, veteran status, disability unrelated to job requirements, genetic information, military service, or other protected status. All qualified applicants will receive consideration for employment without regard to any protected characteristic.
Work Authorization
Applicants must be legally authorized to work in the United States. This is a fully remote position within the United States; visa sponsorship is not available at this time.
Pay: $150,000.00 - $215,000.00 per year
Benefits:
- 401(k) matching
- Dental insurance
- Employee assistance program
- Health insurance
- Life insurance
- Paid time off
- Vision insurance
Application Question(s):
- Are you located within the state of Florida?
- (Optional) Include a brief paragraph on a client success, implementation, or
support function you built or scaled — and what made it work.
Education:
Experience:
- Account management: 5 years (Required)
- Client Excellence: 3 years (Required)
- Leadership: 3 years (Required)
Language:
Willingness to travel:
Work Location: Hybrid remote in Bonita Springs, FL 34134
