Customer Success Lead

Job Title: Customer Success Lead

Reports To: Director of Operations

Job Description

Cloudasta is looking for a full-time seasoned Customer Success Lead to own, grow, and protect the commercial relationships within our high-touch customer base. This is a player-coach role: you will directly manage a Book of Business (BoB) of up to 50 accounts representing approximately ~$4M in total annual Google Workspace spend, while also leading our Solutions team for tactical/low-touch initiatives.

You will be the person our highest-value clients — Directors, VPs, Procurement leads, and C-Suite executives — trust as a strategic partner. Your primary mandate is ensuring clients renew, expand, and view Cloudasta as an indispensable part of their Google ecosystem.

Alongside that, you will be expected to drive Gemini and Google Cloud adoption, execute on expansion opportunities, and develop the playbooks that scale our CS motion across the organization.

This role is distinct from a traditional Customer Success Manager or Key Account Manager. You will carry a full-cycle commercial motion — onboarding, retention, and upsell — while simultaneously building the systems, segmentation, and coaching cadence that allow your Solutions team to handle the tactical, low-touch layer.

Your Responsibilities

Account Management & Retention

• Own a BoB of up to 50 accounts (high-touch), representing ~$4M in total annual Google Workspace spend.
• Drive contract renewals end-to-end, including multi-year Google Workspace agreements and Google product expansions.
• Develop and maintain executive relationships at the Director, VP, and C-Suite level across your accounts.
• Segment your portfolio by churn risk, growth potential, and strategic value — adjusting your cadence accordingly.
• Maintain a target Net Revenue Retention (NRR) of ≥110% and < 8% churn rate annually across your BoB.

Growth & Expansion

• Identify and execute upsell and cross-sell opportunities including Gemini Enterprise, additional Google Workspace SKUs, and Google Cloud services.
• Lead a Solutions team and collaborate with Sales to develop account expansion plans tied to QBRs and annual reviews.
• Actively position Gemini AI features and Google Cloud capabilities during client engagements as part of Cloudasta's value proposition.

Onboarding & Product Adoption

• Lead high-touch onboarding experiences for new and migrated clients, ensuring rapid time-to-value.
• Drive product adoption across Google Workspace, monitoring usage signals to intervene proactively with at-risk accounts.
• Build educational materials, training sessions, and adoption playbooks for Gemini and Workspace best practices.

Team Leadership

• After a 90-day onboarding period, take ownership of the Solutions team, with direct reports transitioning to you.
• Coach and delegate tactical/low-touch account management to your Solutions team, freeing your capacity for strategic high-touch work.
• Establish clear KPIs, SLAs, and workflows for the combined CS + Solutions Success motion.

Operations & Tooling

• Maintain a clean, up-to-date CRM pipeline across all accounts and contacts in your BoB.
• Report on key CS metrics weekly and prepare executive summaries for leadership reviews.
• Partner with the Director of Operations to refine CS SOPs, health scoring models, and renewal workflows.

Our Candidate

• You have 3+ years of experience in a full-cycle Customer Success, Account Management, or Commercial AM role — you have owned renewals, driven upsells, and managed a real book of business with ARR targets.
• You are genuinely client-facing. You are comfortable and confident in front of C-level executives, VPs, and Procurement teams — over video, in writing, and in live strategy sessions.
• You think commercially. You understand the difference between a support interaction and a revenue conversation, and you know how to navigate both.
• You are organized and process-driven. You thrive when managing a high-volume portfolio and have a system for triaging urgency, tracking your pipeline, and staying ahead of churn signals.
• You are a leader-in-the-making (or already one). You are comfortable mentoring, delegating, and being accountable for a small team's output.
• You write exceptionally well in English. Client communications should require minimal editing. You know how to strike the right tone with an executive vs. a technical lead.
• You are curious about AI in the context of real business workflows. You understand or can quickly learn how Gemini integrates with Google Workspace and why that matters to a leadership team.
• You are self-directed and proactive. You identify what needs to happen next before being asked, and you follow through.
• Google Workspace familiarity is a strong plus. A GWS Admin or GCP certification, or demonstrable product knowledge, meaningfully reduces ramp up time.

Compensation

• We offer competitive base pay with a highly rewarding performance-based bonus structure. The variable incentive is designed to directly reward your impact on Net Revenue Retention (NRR) and growth.

Work Location

• This is a 100% remote opportunity! Preference for candidates in Central or Eastern U.S. time zones.

If you are a motivated and results-oriented individual who is looking for a challenging and rewarding opportunity, we look forward to hearing from you!