Head of Customer Success

Trove; Encinitas (CA); Hybrid; USD 105,000 - 165,000; Full time

Benefits offered by this job

Hybrid work

NDR-based bonus

Competitive base salary

Job summary

Trove is seeking a hands-on Head of Customer Success to manage ~100 dealership accounts, drive retention, and scale an AI-first CS engine. The role combines client leadership with operational rigor, reporting into a lean, bootstrapped team.

In Encinitas, you’ll work 3 days on-site with 2 days remote, overseeing a support specialist and contractors while pushing for above-market compensation tied to Net Dollar Retention and expansion revenue.

Qualifications

• 3-6+ years in CS management or senior account management in B2B SaaS or tech-enabled services.
• Hands-on player-coach mindset, managing accounts daily while optimizing team workflows.
• AI & automation mindset with practical experience using AI tools to streamline processes.
• Experience owning revenue retention metrics (GRR/NRR) and identifying upsell opportunities.
• Local presence: able to work in Encinitas office 3 days a week.

Responsibilities

• Direct account management for ~100 dealership clients.
• Own Net Dollar Retention and renewals across the customer lifecycle.
• Bridge software and ad services to maximize client ROI.
• Implement AI CS workflows to scale service capacity.
• Scale operations leanly with automated workflows and documented processes.
• Coordinate with contractors and internal teams to deliver against commitments.
• Capture dealer feedback and feed it into product and marketing loops.
• Align monthly ad campaigns with dealership sales performance.

Skills

Account management

Leadership

AI & automation

Retention & growth

B2B SaaS

Tools

LLMs

Zapier/Make

Automated reporting tools

Job description

Location: Hybrid (3 days/week in Encinitas, CA)

Type: Full-Time

Compensation: Competitive Base + High-Upside NDR Bonus

About Trove

Trove is the vertical SaaS and digital marketing platform purpose-built for the manufactured and modular home industry. We build the website, CRM, and automated marketing tools that independent home dealers use to attract leads, convert buyers, and close more deals. Our managed digital marketing service (Facebook, Instagram, and Google Ads) is a core part of our platform- dealers trust us to run their ad spend so they can focus on closing deals on the lot.

The Opportunity

We are looking for a hands-on Head of Customer Success who thrives at the intersection of client relationship management, ad service execution, and modern AI automation.

In this role, you will be our primary "player-coach" owning customer retention and success across our entire roster of ~100 dealership accounts. You will manage a full-time support specialist and a bench of contractor partners, while building an AI-first CS engine designed to scale service capacity without inflating headcount.

If you achieve high retention, drive expansion revenue, and build an operationally efficient CS function, we will compensate you above market rates with direct financial upside on Net Dollar Retention (NDR).

What You'll Do

• Direct Account Management: Serve as the main strategic partner and escalation lead for our dealership clients (~100 accounts).
• Drive Net Dollar Retention (NDR): Own retention, renewals, and upsells across the customer lifecycle. Identify churn risks early and actively partner with dealers on growth tactics.
• Bridge Software & Ad Services: Help dealers realize maximum ROI from both our SaaS platform (CRM/Websites) and managed ad campaigns (Facebook, Instagram, Google).

2. Operational Excellence & AI Scaling

• Implement AI CS Workflows: Leverage modern AI tools (e.g., AI call summaries, automated ticket support, auto-generated ad performance reporting, predictive churn signals) to streamline daily client touchpoints.
• Scale Leanly: Build automated workflows and documentation that allow our team to handle 2-3x account growth while keeping the core team lean.
• Team & Contractor Coordination: Direct our 1 full-time support specialist and manage day-to-day deliverables with our external ad ops and technical contractors.

3. Product & Marketing Feedback Loop

• Voice of the Customer: Route direct dealer feedback to leadership and product engineering to continuously refine Trove's SaaS and marketing offerings.
• Ad Campaign Alignment: Partner with ad contractors to ensure monthly campaign performance maps directly to dealer sales volume.

What We're Looking For

• 3-6+ Years in CS Management or Senior Account Management: Background in B2B SaaS, tech-enabled services, or performance marketing agencies managing mid-market clients.
• Hands-on Player-Coach Mentality: Comfortable actively managing accounts daily while simultaneously optimizing team workflows.
• AI & Automation Mindset: Practical experience using modern software and AI tools (LLMs, Zapier/Make, automated reporting tools) to eliminate manual administration.
• Retention & Growth Ownership: Proven track record holding revenue retention metrics (GRR/NRR) and identifying natural upsell/expansion opportunities.
• Local Presence: Able to work in-office 3 days a week in either our Encinitas office.

Bonus Points

• Experience in Real Estate, Automotive, Dealership SaaS, or Vertical B2B SaaS.
• Familiarity with digital ad channels (Facebook, Instagram, and Google Ads).

Aligned with our lean, high-performing bootstrapped structure, we provide competitive cash pay with high variable upside tied to department efficiency and retention:

• Base Salary: $105,000 - $135,000 (dependent on location and experience).
• Variable Bonus (Tied to NDR): $15,000 - $30,000+ uncapped performance bonus tied directly to Net Dollar Retention and expansion revenue.
• Total Target Earnings (OTE): $120,000 - $165,000+.
• Hybrid Work: 3 days in office (Sausalito or San Diego), 2 days remote.