Senior Director, Customer Success (RapidScale) (Remote)

Job Summary

Company

Overview

RapidScale is establishing Customer Success as a core revenue-adjacent capability designed to ensure delivery of contracted business outcomes and measurable business value, improve customer advocacy, drive gross revenue retention, and enable expansion.

The Senior

Director, Customer Success is accountable for owning customer outcomes and value realization, while acting as the orchestrator / quarterback across the entire RapidScale ecosystem—Sales (AEs/AMs), Delivery, Operations, Consulting, Support, and administrative billing.

This role builds the system that ensures customers consistently experience RapidScale as one accountable partner, not a collection of teams. This role directly protects revenue durability, customer lifetime value, and enterprise credibility. By owning outcomes, building segment-specific playbooks, and acting as RapidScale’s internal quarterback, the Senior Director of Customer Success ensures customer success is repeatable, scalable, and growth-generating.

Strategic Objectives

  • Ensure customers realize measurable business outcomes and value from RapidScale solutions
  • Improve Gross Revenue Retention (GRR) from ~78% toward 80–85%+ near term and 85–90%+ over time
  • Reduce churn and downsell through proactive lifecycle management and expectation alignment
  • Institutionalize a single accountable customer advocate and internal orchestration model
  • Scale Customer Success through repeatable programs and playbooks by customer segment
  • Enable expansion by surfacing Customer Success Qualified Leads (CSQLs) to Sales

Responsibilities

Core Responsibilities

Business Outcomes & Value Realization (Primary Accountability)

  • Own accountability for ensuring RapidScale delivers the business outcomes and business value committed to customers
  • Ensure every Gold+ customer has a clearly defined Outcome-Based Success Plan (OBSP) tied to customer objectives, KPIs, and value realization milestones
  • Validate that delivery, consulting, and operational activities remain aligned to outcomes—not just scope completion
  • Lead executive-level value realization discussions with customer stakeholders
Customer Success Strategy, Programs & Playbooks
  • Design, develop, and continuously evolve Customer Success programs and playbooks by customer segment:
  • Diamond: Executive partnership, white-glove orchestration, strategic roadmap alignment
  • Platinum: Proactive value realization, adoption acceleration, expansion readiness
  • Gold: Structured onboarding, standardized engagement, outcome validation
  • Define segment-specific engagement models, lifecycle touchpoints, success metrics, and escalation paths
  • Ensure playbooks are operationalized through tooling, enablement, and governance—not left as static documents
  • Standardize best practices while preserving flexibility for complex enterprise environments
Quarterback & Cross-Functional Orchestration
  • Act as the orchestrator / quarterback across all RapidScale functions involved in the customer lifecycle, including:

    Sales (AEs and AMs)

  • Delivery and Operations
  • Consulting and Professional Services
  • Support and Cloud Engineering
  • Administrative and billing functions
  • Ensure seamless handoffs, clear accountability, and coordinated execution across teams
  • Proactively resolve cross-functional friction impacting customer outcomes, timelines, or experience
Retention, Renewal & Expansion Enablement
  • Own renewal readiness in close partnership with Sales and Account Management
  • Ensure early renewal conversations grounded in delivered value and outcomes
  • Enable expansion by identifying unmet needs, adoption signals, and Customer Success Qualified Leads (CSQLs)
  • Maintain clear role boundaries between Customer Success and commercial ownership while remaining tightly aligned
Customer Experience & Executive Engagement
  • Standardize proactive communication, progress updates, and transparency into risks or delays
  • Elevate QBRs to focus on outcomes achieved, value delivered, and forward-looking roadmaps
  • Ensure customers experience RapidScale as a coordinated, accountable enterprise partner
Team Leadership & Capability Building
  • Build, lead, and develop the Customer Success leadership team and CSM organization
  • Establish performance standards, coaching rigor, and clear career progression paths aligned to customer tiers
  • Foster a culture of ownership, accountability, and continuous improvement

    Metrics, Governance & Insights

Own CS KPIs including:
  • Gross Revenue Retention (GRR)
  • Net Revenue Retention (NRR)
  • Customer Success Qualified Leads (CSQLs)
  • Customer health scores
  • Team-level CS NPS
  • Implement governance, operating cadence, and executive reporting to the CRO and RSLT

Qualifications

Experience & Qualifications
  • BA/BS degree with 12+ years of relevant experience including: Customer Success, Client Services, Enterprise Account Leadership, or Consulting within B2B technology or services OR equivalent combination of education and experience (MS + 10 years of experience or P.D. + 7 years of experience or 16 years of experience with no degree)
  • 7+ years of experience in a leadership role
  • Excellent communication and interpersonal skills, with the ability to build relationships and influence key stakeholders
  • Proven experience designing scalable Customer Success programs and playbooks, not just managing accounts
  • Strong background in managed services, cloud, SaaS, or complex enterprise delivery environments
  • Demonstrated ability to orchestrate cross-functional execution in matrixed organizations
  • Executive presence with customers and senior internal leaders
Leadership Attributes:
  • Outcome-obsessed, enterprise-minded, and commercially astute
  • High EQ, low ego; trusted integrator across functions
  • Structured, decisive, and comfortable driving accountability at scale
  • Data-driven with a bias toward execution and value realization
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Common Interview Questions And Answers

1. HOW DO YOU PLAN YOUR DAY?

This is what this question poses: When do you focus and start working seriously? What are the hours you work optimally? Are you a night owl? A morning bird? Remote teams can be made up of people working on different shifts and around the world, so you won't necessarily be stuck in the 9-5 schedule if it's not for you...

2. HOW DO YOU USE THE DIFFERENT COMMUNICATION TOOLS IN DIFFERENT SITUATIONS?

When you're working on a remote team, there's no way to chat in the hallway between meetings or catch up on the latest project during an office carpool. Therefore, virtual communication will be absolutely essential to get your work done...

3. WHAT IS "WORKING REMOTE" REALLY FOR YOU?

Many people want to work remotely because of the flexibility it allows. You can work anywhere and at any time of the day...

4. WHAT DO YOU NEED IN YOUR PHYSICAL WORKSPACE TO SUCCEED IN YOUR WORK?

With this question, companies are looking to see what equipment they may need to provide you with and to verify how aware you are of what remote working could mean for you physically and logistically...

5. HOW DO YOU PROCESS INFORMATION?

Several years ago, I was working in a team to plan a big event. My supervisor made us all work as a team before the big day. One of our activities has been to find out how each of us processes information...

6. HOW DO YOU MANAGE THE CALENDAR AND THE PROGRAM? WHICH APPLICATIONS / SYSTEM DO YOU USE?

Or you may receive even more specific questions, such as: What's on your calendar? Do you plan blocks of time to do certain types of work? Do you have an open calendar that everyone can see?...

7. HOW DO YOU ORGANIZE FILES, LINKS, AND TABS ON YOUR COMPUTER?

Just like your schedule, how you track files and other information is very important. After all, everything is digital!...

8. HOW TO PRIORITIZE WORK?

The day I watched Marie Forleo's film separating the important from the urgent, my life changed. Not all remote jobs start fast, but most of them are...

9. HOW DO YOU PREPARE FOR A MEETING AND PREPARE A MEETING? WHAT DO YOU SEE HAPPENING DURING THE MEETING?

Just as communication is essential when working remotely, so is organization. Because you won't have those opportunities in the elevator or a casual conversation in the lunchroom, you should take advantage of the little time you have in a video or phone conference...

10. HOW DO YOU USE TECHNOLOGY ON A DAILY BASIS, IN YOUR WORK AND FOR YOUR PLEASURE?

This is a great question because it shows your comfort level with technology, which is very important for a remote worker because you will be working with technology over time...

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