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Salary: USD 70,000 - 90,000 / annual
FlexPoint is a venture-backed SaaS provider of payments and financial solutions for the Managed IT Services (MSP) industry, having raised $19.5M from top-tier investors.
As Implementation Specialist, you will own the technical onboarding of new MSP customers, taking them from signed contract to live, paying, and fully adopted within 30 days or less. You'll manage the complete technical implementation lifecycle including PSA and accounting integrations (ConnectWise, Autotask, HaloPSA, QuickBooks Online, Xero), payment migrations from legacy processors, and customer training. You'll also run the onboarding pipeline, leading daily standups and weekly pipeline reviews with leadership.
Key responsibilities include:
- Guiding customers through kickoff, setup, and launch with clear milestones
- Configuring and testing integrations, documenting workflows, and confirming first successful payments
- Running payment migrations by coordinating with customers, Product, and Engineering teams
- Delivering live training on invoicing, notifications, reconciliation, and building self-serve learning content
- Driving feature adoption (AutoPay, notifications, stored payment methods, Same-Day ACH)
- Leading weekly pipeline reviews and identifying stalled accounts within two weeks for recovery
- Owning onboarding support tickets and troubleshooting issues
- Writing help-center articles, creating macros, and identifying automation opportunities
- Designing and maintaining in-app guides, checklists, and workflows using digital adoption tools like Pendo
- Handing off graduated customers to Customer Success Managers with clear goals and growth opportunities
Your first 90 days: Days 1-30 involve learning the product, payment migration process, and tools while shadowing and taking ownership of the ticket queue. Days 30-60 you'll run standups and pipeline reviews independently, owning migrations and training end-to-end. By day 90, you'll resolve most issues without escalation, reduce stuck accounts, and ship help center and training improvements.
Success is measured by: customers live within 30 days, 90%+ onboarding graduation rate, post-onboarding NPS of +30 or higher, on-time payment migrations, and strong support response times.
REQUIREMENTS:
- 2–4 years in SaaS implementation, onboarding, customer success, or technical support, taking customers from contract to go-live
- Hands-on experience with software integrations or data migrations; comfortable troubleshooting sync errors and setup issues independently
- Strong project management skills; ability to keep many accounts moving with clear next steps and clean records
- Comfort presenting pipeline status and KPIs to leadership
- Clear, calm communication with finance teams and business owners, including resetting expectations
- Strong writing skills for help articles, macros, and process documentation
NICE TO HAVE:
- Experience in or with MSPs, or with tools like ConnectWise, Autotask, HaloPSA, Kaseya BMS, Syncro
- Payments or fintech background, especially migrating customers between payment processors
- Experience with HubSpot, Zendesk, customer success platforms (Custify, Gainsight, ChurnZero), LMS, or digital adoption platforms (Pendo, WalkMe, Appcues, Userpilot)
- Working knowledge of billing and payments: invoicing, ACH, card processing, AutoPay, reconciliation
- Startup experience and comfort switching between hands-on work and building process
