PSS Activations Specialist

The Payment Success Specialist – Activation is a pivotal, high-impact role that shapes the first impression and long-term success of Weave’s payments customers. As a trusted advisor and subject matter expert, you will lead customers through a strategic, white-glove onboarding journey — transforming the activation experience into a catalyst for sustained adoption, revenue growth, and operational transformation.

In this role, you are not simply enabling transactions — you are architecting how new customers integrate payments into their business model from day one. You’ll design activation strategies tailored to each customer’s workflows, train their teams with precision, and guide them through early adoption milestones that lay the foundation for long-term success. Your ability to influence behavior, anticipate challenges, and drive measurable outcomes will directly impact retention, revenue, and customer lifetime value.

This role reports to the Manager of Payment Success

This role is hybrid in office

What You’ll Own

Strategic Activation & Onboarding

• Serve as the primary consultant and trusted advisor for new payments customers, delivering a world-class onboarding experience from kickoff to activation.

• Lead comprehensive Payment Success Introduction + Training Calls that go beyond setup — aligning Weave’s capabilities with the customer’s operational goals and success metrics.

• Ensure flawless deployment of hardware, software, and Text-to-Pay workflows, guiding customers through best-practice configurations and tailored implementation plans.

• Design activation roadmaps that strategically guide customers toward their first milestones, including completing three transactions with unique customers ,while embedding Weave Payments into daily operations.

• Establish clear activation success criteria and set expectations for adoption, usage, and continued engagement.

Customer Enablement & Value Realization

• Conduct proactive follow-up engagements with key stakeholders, assessing adoption progress and identifying opportunities for optimization.

• Deliver strategic recommendations to remove barriers, streamline workflows, and maximize payment utilization — positioning Weave as a mission-critical revenue tool.

• Act as a payments SME, advising customers on industry best practices, regulatory nuances, and operational strategies that improve financial performance.

Post-Activation Success & Growth Acceleration

• Monitor customer processing volume for six months post-activation, using data-driven insights to identify opportunities for increased usage and deeper platform adoption.

• Strategically guide customers toward reaching $5,000 in monthly processing volume — positioning them as Meaningful Volume Customers (MVC) and unlocking the full potential of Weave Payments.

• Partner with internal stakeholders across Customer Success, Sales, and Product to share activation trends, feedback, and market intelligence that shape go-to-market strategy.

What You Will Need to Accomplish the Job

• 5+ years of experience in customer onboarding, activation, customer success, or implementation — preferably within SaaS, FinTech, or payments.

• Proven expertise in payments technology, workflows, and best practices, with the ability to consult at a strategic level.

• Exceptional communication and facilitation skills, including experience engaging with business owners, operations leaders, and financial decision-makers.

• Advanced problem-solving skills — with the ability to proactively identify adoption risks, design tailored solutions, and influence outcomes.

• Deep understanding of change management and how to guide customers through behavioral and operational shifts.

• A results-driven mindset — consistently meeting or exceeding activation, volume, and adoption KPIs.

• Highly collaborative and cross-functional — thrives on working with Sales, Product, and Support teams to deliver a seamless, high-impact customer experience.

What Will Make Us Love You

• Deep subject-matter expertise in payments, including knowledge of processing platforms, merchant onboarding, and transaction lifecycle.

• Experience driving adoption of Stripe or similar payments solutions.

• A track record of transforming onboarding into a revenue-accelerating motion, not just a support function.

• Exceptional emotional intelligence and consultative skills — with the ability to influence behavior, build trust, and create advocates from day one.

• A passion for delivering white-glove experiences that set the standard for customer excellence.

At Weave, we use Artificial Intelligence (AI) tools to help us work more efficiently and create a smoother candidate experience. AI may assist with things like writing job descriptions, scheduling interviews, or reviewing applications against job-related criteria. For additional information, please review the External AI Policy Statement available on our Careers page.

Weave is an equal opportunity employer that is committed to fostering an inclusive workplace where all individuals are valued and supported. We welcome anyone who is hungry to learn, problem-solve and progress regardless of race, color, ancestry, religion, sex, national origin, sexual orientation, age, citizenship, marital status, disability, gender identity, veteran status, or other applicable legally protected characteristics. If you have a disability or special need that requires accommodation, please let us know.

All official correspondence will occur through Weave branded email. We will never ask you to share bank account information, cash a check from us, or purchase software or equipment as part of your interview or hiring process.