DeepWork Portfolio Careers

About Crowded

Crowded is a financial technology platform built to empower complex, multi-entity organizations, including camps, nonprofits, associations, sports clubs, and Girl Scout councils. By simplifying banking, payments, and financial management across sub-accounts, per diem cards, and chapter tracking, we help organizations operate with transparency, compliance, control, and scale.

Role Overview

We are seeking a Senior Customer Success Manager to own and grow a portfolio of Mid-Market and Enterprise customers. This role is responsible for driving net dollar retention, expansion, and long-term strategic partnerships across Crowded’s most complex and high-impact accounts.

You will act as a trusted advisor to executive stakeholders, finance leaders, and operational owners, guiding customers through adoption, expansion, renewals, and organizational scale. This role requires comfort navigating multi-entity account structures, longer sales cycles, and revenue-driven success motions.

This position is ideal for a senior CSM who blends relationship management, commercial ownership, and strategic problem-solving and who wants direct influence over revenue outcomes.

Key Responsibilities

Account Ownership & Strategy

• Own a portfolio of Mid-Market and Enterprise accounts, serving as the primary strategic relationship owner post-onboarding.

• Develop and execute account success plans aligned to customer goals, contract structure, and expansion potential.

• Build trusted relationships with senior stakeholders including CFOs, executive directors, and national finance leaders.

Retention, Expansion & Revenue Growth

• Drive net dollar retention (NDR) through proactive adoption, expansion, and renewal management.

• Identify, position, and close expansion opportunities including additional sub-accounts, per diem programs, processing volume growth, and premium platform features.

• Lead renewal conversations, negotiate multi-year agreements, and partner cross-functionally to secure long-term commitments.

• Forecast renewals and expansion accurately using Salesforce and internal reporting tools.

Customer Outcomes & Advocacy

• Lead executive business reviews/QBRs focused on outcomes, ROI, and future-state planning.

• Act as the voice of the customer, providing structured feedback to Product, Operations, and Leadership.

• Identify and cultivate customer champions, references, and long-term advocates.

• Drive adoption and continued onboarding of different EIN customers with a National relationship.

Cross-Functional Leadership

• Partner closely with Sales, Onboarding, Support, Product, and Finance to deliver a cohesive customer experience.

• Support complex transitions such as migrations, organizational restructures, and large-scale rollouts.

• Contribute to process improvement, playbooks, and scalable CS motions for Mid-Market and Enterprise customers.

Qualifications

• 5+ years of experience in Customer Success, Account Management, or a similar client-facing SaaS or fintech role.

• Direct experience managing Mid-Market and/or Enterprise accounts with complex stakeholders and account structures.

• Proven track record of owning renewals and expansion revenue in a quota- or target-carrying role.

• Strong executive presence with the ability to influence and advise senior decision-makers.

• Experience supporting multi-entity or federated organizations (e.g., chapters, franchises, districts, councils).

• Highly organized, proactive, and comfortable operating in ambiguity.

• Proficiency with Salesforce and data-driven account management.

Compensation & Benefits

• OTE of $130,000–$140,000, consisting of a competitive base salary based on experience, and a performance-based variable tied to retention and expansion.

• Comprehensive health, dental, and vision benefits.

• Collaborative, mission-driven culture with high ownership and visibility.

• Opportunity to shape and scale Customer Success at a high-growth fintech serving mission-driven organizations.