Onboarding Specialist

About Puzzle

At Puzzle, we’re not just building accounting software — we’re reimagining how modern startups and small businesses understand and run their finances. Our platform brings real-time accounting, automation, and deep fintech integrations together so founders always know where they stand. Our mission is to make accounting intuitive, transparent, and genuinely helpful.

About the Role

To support our growing customer base, we’re looking for an Onboarding Specialist to guide new customers through their first and most critical moments with Puzzle. This role is highly customer-facing and ideal for someone who loves talking to people, understands bookkeeping fundamentals, and thrives in a fast-moving startup environment. As an Onboarding Specialist, you’ll be the primary point of contact for new customers during their early journey with Puzzle. You’ll help them understand their numbers, configure their accounts correctly, and feel confident using our platform from day one. You’ll act as a trusted guide, translating accounting concepts into plain language and ensuring customers are set up for long-term success. This role is perfect for someone who enjoys building relationships, explaining complex topics simply, and being on the front lines with customers. This is an opportunity to join a well-funded, fast-growing startup led by experienced founders and make a real impact on how modern businesses experience accounting. If you love helping people, enjoy talking through numbers, and want to shape the customer experience from the ground up, we’d love to meet you.

What You’ll Do

• Lead 1:1 onboarding calls with new customers to set up their Puzzle account and core workflows
• Guide customers through bookkeeping and accounting concepts relevant to startups and small businesses
• Support data migrations from other accounting platforms (e.g., QuickBooks, Xero), ensuring accuracy and a smooth transition
• Serve as a friendly, knowledgeable first point of contact via video, email, and chat
• Proactively identify gaps, risks, or opportunities during onboarding and recommend best practices
• Partner closely with Customer Success, Product, and Engineering teams to surface feedback and improve the onboarding experience
• Help refine onboarding playbooks, templates, and documentation as we scale
• Ensure customers complete onboarding feeling confident, informed, and excited to use Puzzle

Who You Are

• 1–3 years of customer-facing experience (customer success, onboarding, support, accounting, or similar)
• Working knowledge of bookkeeping and accounting fundamentals is a must
• Strong verbal and written communication skills - able to explain complex ideas clearly and empathetically
• Energized by talking to customers and building relationships
• Highly organized and comfortable managing multiple onboarding workflows at once
• Curious, adaptable, and excited to learn new tools and processes

Nice-to-Haves

• Experience onboarding customers in a B2B SaaS environment
• Familiarity with startup accounting and common tools (QuickBooks, Xero, Stripe, Gusto, etc.)
• Background in accounting, finance, or bookkeeping
• Experience working at a startup or fast-growing company

What's 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 pay
• 100% paid employee health, dental, and vision plans (U.S. & Canada vary)
• 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

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. 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.

Key skills/competency

• Customer Onboarding
• Bookkeeping Fundamentals
• SaaS
• Customer Success
• Relationship Building
• Communication Skills
• Problem Solving
• Data Migration
• Startup Environment
• Fintech