Scaled Customer Success Manager

At Puzzle, we're not just building accounting software - we're fundamentally reimagining it. Our cutting-edge platform seamlessly integrates with modern fintech tools, offering founders and finance teams a real-time and comprehensive view of their finances like never before.

Our mission is to empower businesses with seamless financial operations, realtime insights and free accountants from rote tasks. To help us achieve our goals, we're looking for an experienced Scaled Customer Success Manager to drive adoption, retention, and growth across a high-volume portfolio of small to mid-sized finance teams.

What Were Looking For

As a Scaled Customer Success Manager, you'll own the customer journey for 100+ accounts, ensuring strong product adoption, retention, and expansion. You'll be a strategic partner who understands how to deliver exceptional value at scale through creative outreach, data-driven interventions, and a deep understanding of accounting workflows.

This role combines your accounting and bookkeeping expertise with scaled customer success best practices. You'll proactively identify at-risk accounts, drive feature adoption, manage renewal conversations, and create scalable playbooks that ensure customers unlock the full potential of Puzzle's financial platform. If you thrive on balancing automation with human touch and love empowering finance teams with cutting-edge technology, this role is perfect for you.

This is your opportunity to join a well-funded startup led by accomplished founders. Join us remotely from anywhere in the US or Canada.

What You'll Do

Portfolio Management & Retention

Own and manage a portfolio of 100s of small to mid-sized customer accounts, ensuring strong retention, product adoption, and customer health at scale

Monitor product usage data and health scores to identify trends, adoption gaps, and churn risks across your portfolio

Proactively intervene with at-risk accounts through targeted outreach, value reinforcement content, and personalized engagement strategies

Lead renewal conversations by showcasing ROI, usage trends, and opportunities for expanded valueeven with hard-to-reach customers

Scaled Engagement & Enablement

Deliver value through scalable, creative methods including Loom videos, email campaigns, group webinars, office hours, and asynchronous training resources

Conduct 1 : 1 training calls and Zoom check-ins when high-touch engagement is warranted

Develop and refine customer success playbooks, email sequences, and automated workflows for onboarding, adoption, and renewal stages

Create compelling written content that articulates Puzzle's ROI and educates customers on maximizing platform capabilities

Guide customers through complex accounting migrations and platform configurations with a consultative approach

Cross-functional Collaboration & Strategy

Partner with Product, Engineering, and Support teams to escalate technical issues, advocate for customer needs, and influence product roadmap priorities

Collaborate with Marketing and CS leadership to design and execute scaled engagement campaigns, lifecycle programs, and customer education initiatives

Build and maintain robust documentation, knowledge base articles, FAQs, and best practice resources

Maintain accurate records in CRM (HubSpot or similar), ensuring data hygiene and actionable insights for leadership

Strategic Impact

Surface customer insights, feature requests, and market trends to inform product strategy and go-to-market initiatives

Identify expansion opportunities and champion upsell conversations where appropriate

Contribute to the evolution of Puzzle's scaled customer success motion and operational excellence

Who You Are

4+ years of customer-facing experience in customer success, account management, or similar roles within B2B SaaS

2+ years managing scaled / lifecycle customer success programs or high-volume SMB / mid-market segments

Proven track record of managing 100+ accounts simultaneously while maintaining high retention and satisfaction rates

Strong understanding of accounting and bookkeeping principles with ability to speak credibly to finance professionals about workflows, reconciliations, and reporting

Exceptional written communication skills- you can craft persuasive emails, clear training documentation, and compelling product narratives

Data-driven mindset with ability to analyze usage patterns, identify churn signals, and take proactive intervention steps

Highly organized with a systems-oriented approach to workflows, segmentation, and process optimization

Self-starter who thrives in ambiguity and fast-paced, evolving startup environments

Bachelor's degree in accounting, finance, business, or related field (or equivalent experience)

Nice-to-Haves

Experience with accounting platforms (QuickBooks, Xero, NetSuite, etc.) and understanding of financial workflows

Familiarity with customer success platforms (Vitally, ChurnZero, Gainsight) and product analytics tools (Mixpanel, Amplitude)

Proficiency with CRM systems (HubSpot preferred) and support / engagement tools (Intercom, Zendesk)

Experience at a fintech, financial services SaaS, or accounting technology startup

Background supporting professional services teams (accounting firms, finance departments, CFO offices)

Track record of building scaled CS programs, playbooks, or automation workflows from scratch

Whats in it for you?

Join Puzzle Financial at a pivotal growth stage where you'll help redefine and reimagine how companies handle their financials while building your career in a flexible, remote-first environment. You'll have the opportunity to make a significant impact, work with innovative founders, and develop valuable expertise at the intersection of modern accounting and fintech.

Here is a preview of some of the amazing benefits here at Puzzle :

Competitive base pay and meaningful equity

100% paid employee health, dental, and vision plans

10 observed holidays and a flexible PTO policy so you can recharge

$1000 home office budget to get you set up for success

$2400 co-working budget for face time with your colleagues

$600 learning and development budget

401K so you can save for your future

And much more

• Visa Sponsorship Notice : Puzzle does not provide visa sponsorship for new hires at this time. We can only consider candidates who are legally authorized to work in the U.S. or Canada without requiring new visa sponsorship or transfer of an existing visa.

Candidates should be currently residing in the U.S. or Canada to be eligible for this position. If hired, you will be required to present proof of work authorization. This employer is a participant of the E-Verify program.

Puzzle is an equal opportunity and affirmative action employer. We welcome and encourage diversity in the workplace regardless of gender, race or color, ethnicity or national origin, age, disability, religion, sexual orientation, gender identity or expression, veteran status, or any other characteristics protected by law.