Implementation Specialist

About the job

Implementation Specialist, FlexPoint

Location: Remote (US) · Type: Full-time · Team: Customer Success

About FlexPoint

FlexPoint is a rapidly growing venture-backed Software as a Service (SaaS) provider of payments and financial solutions for the Managed IT Services (MSP) industry. FlexPoint has raised $19.5M in funding from top-tier venture investors to date and is a fast-growing startup with employees distributed across the United States.

About the role

As our Implementation Specialist, you'll take new MSP customers from signed contract to live, paying and fully adopted in 30 days or less. You'll own the technical side of onboarding: PSA and accounting integrations, payment migrations from legacy processors, and customer training. You'll also run our onboarding pipeline, leading daily standups and the weekly pipeline review with leadership.

You'll work closely with our Customer Success Managers, who own the long-term relationship, and hand off customers at graduation ready to renew and grow. If you like solving technical puzzles, keeping a lot of projects moving at once, and seeing a customer's first payment land, this role is for you.

What you'll do

• Get customers live. Guide each new customer from sales handoff through kickoff, setup, and launch, hitting clear milestones at every stage.
• Own integrations. Configure and test PSA and accounting integrations (ConnectWise, Autotask, HaloPSA, QuickBooks Online, Xero and more), document customer workflows, and confirm a first successful payment.
• Run payment migrations. Move customers' stored payment methods off legacy processors, coordinating with the customer, Product and Engineering teams to finish on time and without disruption.
• Train customers. Deliver live training on invoicing, notifications and reconciliation, and help build our self-serve learning courses.
• Drive adoption. Make sure customers turn on the features that create value, such as AutoPay, notifications, stored payment methods, and Same-Day ACH, before they graduate.
• Run the pipeline. Lead weekly pipeline review with leadership: who's moving, who's stuck, what's blocking them, and who owns the next step.
• Catch risks early. Spot stalled accounts within the first two weeks and run a structured recovery plan, so no customer falls through the cracks.
• Solve problems. Own onboarding support tickets, troubleshoot most issues yourself, and know when to escalate.
• Make it scale. Write help-center articles and macros, find repetitive work to automate, and share customer feedback with Product.
• Build in-product automation. Design and maintain in-app guides, checklists, tooltips and triggered workflows in a digital adoption tool like Pendo, so customers can self-onboard and adopt key features without waiting on a call.
• Hand off well. Transition graduated customers to their CSM with a clear picture of goals, risks and growth opportunities.

Your first 90 days

• 30 days: Learn the FlexPoint product, our payment migration process and our tools. Shadow kickoffs and training sessions and take ownership of the onboarding ticket queue.
• 60 days: Run daily standups and the weekly pipeline review on your own. Own payment migrations and customer training end to end.
• 90 days: Resolve most onboarding issues without escalation, cut the number of stuck accounts, and ship your first help center and training improvements.

How we measure success

customers live within 30 days of kickoff, a 90%+ onboarding graduation rate, post-onboarding NPS of +30 or higher, payment migrations completed on time, and strong support response times.

What you bring

• 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. You're comfortable troubleshooting sync errors and setup issues on your own.
• Strong project management. You keep many accounts moving at once, with clear next steps and clean records.
• Comfort running a meeting with data. You can present pipeline status and KPIs to leadership.
• Clear, calm communication with finance teams and business owners, including when you need to reset expectations.
• Strong writing skills for help articles, macros and process docs.

Nice to have

• Experience in or with MSPs, or with tools like ConnectWise, Autotask, HaloPSA, Kaseya BMS, Syncro, QuickBooks Online or Xero.
• Payments or fintech background, especially migrating customers between payment processors.
• Experience with HubSpot, Zendesk, a customer success platform (Custify, Gainsight, ChurnZero), an LMS, or a digital adoption platform (Pendo, WalkMe, Appcues, Userpilot).
• A working grasp of billing and payments: invoicing, ACH, card processing, AutoPay and reconciliation.
• Startup experience. You're happy switching between hands-on work and building process.

Compensation and benefits

• Base salary: $70,000–$90,000 USD, based on experience
• Remote: fully remote team, with top-tier equipment and work-from-home setup gear
• Employee equity plan as part of a competitive compensation package
• Health, dental and vision: high-quality plans, 100% employer-paid
• Unlimited PTO plus paid company holidays
• 401(k) with a 3% company match

FlexPoint is committed to fostering, cultivating, and preserving a culture of diversity and inclusion. We believe in equal treatment and opportunity for all staff and strive to actively build a diverse workforce where everyone is treated equally. Everyone has a responsibility to treat others with dignity and respect, and make sure all people feel included and have access to the same opportunities. We actively strive to create an environment where all people can share their ideas, beliefs, and skills. We are proud to be an Equal Opportunity Employer, committed to equal employment opportunity and equitable compensation regardless of race, gender, religion, sex, sexual orientation, national origin, or disability.