Senior Customer Success Manager, Onboarding & Retention

Senior Customer Success Manager, Onboarding & Retention

Title: Senior Customer Success Manager, Onboarding & Retention 

Company: Puzzle Financial Inc.

Location: U.S. or Canada (Remote)

Job Type: Full-time

Compensation: $75,000 USD/year + equity & benefits package

About Puzzle

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 bookkeeping tedium. To help us achieve our goals, we're looking for an experienced Senior Customer Success Manager to own how new customers get started on Puzzle and why they stay.

What We're Looking For

Most churn starts in a customer's first 30 days . We're hiring our first dedicated owner of onboarding and retention to change that. You'll run onboarding for new customers, own the cancellation and save process end to end, and support our accounting partner firms on the platform.

This role is for someone who has done the books . Former bookkeepers or staff accountants who moved into SaaS customer success or implementation will feel at home here. Our customers range from founders who may not have deep accounting expertise to CPAs and accounting firms who need someone they can talk to as a peer.

You'll play a key role in driving product adoption, customer satisfaction, and retention , and you'll be measured on it. This is an opportunity to join a fast-growing startup, build the playbook rather than follow one, and work closely with customers who are building the next generation of companies.

What You'll Do

Customer Onboarding & Adoption

• Run 1:1 onboarding calls tailored to each customer's accounting setup: entity type, revenue model, payroll, and historical books
• Book onboardings within 3 business days and send written next steps after every call
• Run structured check-ins at days 14, 30, and 60 to make sure customers are getting value from Puzzle
• Build self-serve onboarding paths and resources for simpler accounts so your time goes where it matters most

Retention (Primary Metric)

• Own our cancellation flow and save offers in ChurnKey
• Manage failed-payment recovery and apply our refund policy consistently
• Analyze cancellation feedback weekly and turn it into product and process recommendations
• Monitor customer health to spot at-risk accounts early and reach out before they cancel
• Track save rate and logo churn weekly and report on trends

Partner Support

• Enable our accounting partner firms on the platform
• Respond to partner questions within one business day

Cross-Functional Collaboration

• Work closely with Product, Engineering, and Support teams to escalate issues and advocate for customer needs
• Share customer and churn insights that help shape product improvements
• Recognize when a customer needs full-service accounting help and hand them off cleanly to our Services team

Who You Are

• 3+ years of experience in Customer Success or Implementation in B2B SaaS, following hands-on experience as a bookkeeper or staff accountant
• Solid, practical accounting knowledge: accrual vs. cash, deferred revenue, clearing accounts, payroll entries, and opening balances
• A discovery-first approach: you ask before you demo and tailor every walkthrough to the customer
• Accurate product knowledge, including being clear and upfront about what the product doesn't do
• A track record of owning a churn, retention, or save metric and moving it
• Strong communication skills, comfortable explaining concepts simply to founders and speaking as a peer with CPAs and finance leaders
• Proactive self-starter with an ownership mindset and high attention to detail. You create the process when there isn't one.

Nice-to-Haves

• QuickBooks ProAdvisor or Xero certification; familiarity with QuickBooks, Xero, NetSuite, or similar platforms
• Experience with accounting migrations
• Experience with startup clients (C-corps, SaaS revenue through Stripe)
• Familiarity with ChurnKey, Stripe Billing, Intercom, and/or HubSpot
• Experience working at a fintech, financial SaaS, or accounting technology company
• Based in Central or Eastern time, for morning customer coverage

Your First 90 Days

• Weeks 1–2: Shadow onboarding calls. Learn ChurnKey, Intercom, and our partner history.
• Weeks 3–4: Co-lead onboardings, take over ChurnKey, and start the weekly cancellation-feedback review.
• Weeks 5–8: Run onboarding on your own, launch the day 14/30/60 check-ins, and deliver your first churn readout.
• Weeks 9–12: Own save rate and partner relationships, and ship a self-serve onboarding path.

This role has a clear path to Customer Success Lead , with a scope and level review at 6–12 months.

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 compensation
• 100% paid employee health, dental, and vision plans
• 10 observed holidays and a flexible PTO policy so you can recharge
• Regular company off-sites for face time with your colleagues
• 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.