Puzzle.io is hiring a Scaled Customer Success Manager

Puzzle.io is looking for a Scaled Customer Success Manager to own the customer journey for a portfolio of 100+ accounts. Your mission is to ensure strong product adoption, retention, and expansion by delivering exceptional value at scale through creative outreach and data-driven insights into accounting workflows.

What You'll Do

• Own and manage a portfolio of hundreds 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 value.
• 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.
• 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.
• 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.

What We're Looking For

• 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.
• 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).
• Legally authorized to work in the U.S. or Canada without requiring new visa sponsorship or transfer of an existing visa.
• Currently residing in the U.S. or Canada.

Nice to Have

• 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.

Technical Stack

• HubSpot
• CRM systems
• Customer success platforms (Vitally, ChurnZero, Gainsight)
• Product analytics tools (Mixpanel, Amplitude)
• Support/engagement tools (Intercom, Zendesk)

Team & Environment

You'll collaborate cross-functionally with Product, Engineering, Support, Marketing, and CS leadership.

Benefits & Compensation

• Competitive base pay and meaningful equity
• 100% paid employee health, dental, and vision plans
• 10 observed holidays and a flexible PTO policy
• $1000 home office budget
• $2400 co-working budget
• $600 learning and development budget
• 401K

Work Mode

This role is open to candidates locally based in the U.S. or Canada.

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.