Benepass

• Lead, coach, and develop a team of Technical Account Managers through regular 1:1s, feedback, career development, and performance management. • Foster a culture of curiosity, accountability, continuous learning, and technical growth. • Help teammates build confidence in technical problem-solving, AI-assisted workflows, and customer consulting. • Stay close to the team's work by understanding customer challenges, supporting complex situations, and removing obstacles that prevent the team from succeeding. • Recruit, onboard, and develop new team members as the organization grows. • Create an environment where teammates feel supported, challenged, and empowered to grow their careers. • Partner with the Director of Customer Operations to evolve the Technical Account Management function as the organization grows. • Identify opportunities for greater specialization, segmentation, or changes in team ownership based on customer needs, workload, and business priorities. • Use operational data, team feedback, and firsthand knowledge of day-to-day work to make thoughtful recommendations that improve scalability and team effectiveness. • Help implement organizational changes, new processes, and operating models as the team continues to mature. • Develop team processes and operating rhythms that enable consistent execution while creating capacity to support future growth. • Develop a deep understanding of the team's day-to-day workflows and identify opportunities to improve efficiency, quality, and consistency. • Regularly evaluate recurring work to determine whether it should remain within Technical Account Management, be automated, or be addressed through Product or Engineering improvements. • Build and refine processes that help the team scale while maintaining a high-quality customer experience. • Partner closely with Product, Engineering, Customer Success, and Operations to remove friction and improve cross-functional collaboration. • Monitor team capacity, workload, and operational health to ensure sustainable execution. • Serve as a senior escalation point for complex customer situations, partnering across teams to drive resolution. • Coach the team through technical investigations rather than simply providing answers, helping build long-term technical capability. • Ensure technical customer issues are documented, prioritized, and translated into actionable product or operational improvements. • Build repeatable playbooks and best practices for common technical scenarios. • Encourage thoughtful use of AI tools to improve investigation, documentation, and operational efficiency. • Identify opportunities to automate repetitive work and reduce manual effort across the team. • Champion continuous improvement by helping the team experiment with new tools, workflows, and ways of working. • Build strong partnerships with Product, Engineering, Customer Success, Support, and Operations. • Advocate for customer needs while balancing operational efficiency and product scalability. • Provide structured feedback that helps influence product improvements and operational investments. • Help define clear ownership boundaries between Technical Account Management and partner teams as responsibilities evolve.

• Lead, coach, and develop a team of Customer Success Managers through regular 1:1s, performance management, and career development. • Own team performance across customer retention, renewals, customer health, product adoption, and expansion pipeline generation. • Partner with CSMs on strategic customer relationships, executive conversations, and complex customer escalations. • Establish scalable operating rhythms for account reviews, renewal forecasting, health monitoring, and portfolio management. • Champion the adoption of AI and automation across the Customer Success organization by identifying opportunities to eliminate manual work, improve customer experiences, and enable the team to scale without sacrificing service quality. • Analyze customer and team performance data to identify trends, coaching opportunities, and process improvements. • Partner with Sales to ensure successful customer transitions and identify expansion opportunities. • Collaborate with Implementation, Technical Account Management, Customer Experience, Product, and Engineering to deliver an exceptional end-to-end customer experience. • Build and improve playbooks, customer journeys, and operational processes that enable the team to scale efficiently. • Serve as the voice of the SMB and Mid-Market customer internally by advocating for customer needs and communicating product feedback. • Help recruit, onboard, and develop future Customer Success talent as the organization continues to grow.

Role Description Benepass is looking for a Senior Product Designer to design thoughtful, high-quality product experiences on a small, high-ownership team. This role is ideal for a designer who is strong in execution, cares deeply about craft, and enjoys working on meaningful product problems in close partnership with Product and Engineering. You’ll design real, customer-facing experiences, contribute to the evolution of the product, and see your work ship and iterate over time. This role offers clear ownership, strong collaboration, and the opportunity to do focused, high-impact design work within a supportive team environment. In this role, you’ll be responsible for designing and delivering end-to-end product experiences in close partnership with Product and Engineering. You will: - Design full product pages, flows, and feature areas from early concepts through polished execution - Work closely with a Product Manager to understand goals, requirements, and constraints, and translate them into effective design solutions - Contribute to the design system by applying existing patterns thoughtfully and helping improve consistency and quality - Participate in product discovery and user research to understand user needs and validate design decisions - Iterate on designs based on feedback, data, and usability insights - Communicate design rationale clearly to cross-functional partners - Deliver work reliably and on time, surfacing questions or risks early You’ll be expected to work independently on your designs, while collaborating closely with your manager and teammates to ensure alignment and quality. Qualifications - 3–5+ years of experience as a Product Designer working on digital products - Solid visual design and interaction design skills, with strong attention to detail - Enjoy being hands-on and doing the work - Comfortable owning meaningful design work from start to finish - Can incorporate feedback and context to improve design outcomes - Comfortable working within existing systems and constraints - Communicate clearly and collaborate well with Product and Engineering partners - Curious, thoughtful, and motivated to continue growing your craft - Take accountability seriously and follow through on what you commit to Requirements - Experience working on complex products or in fast-moving environments is a plus - Most interested in fundamentals, judgment, and approach to collaboration Compensation Base salary of $140,000 to $160,000 + equity. Range(s) is subject to change. Benepass takes a number of factors into account when determining individual starting pay, including market comparables, interview performance, peer compensation, and years of experience. Benefits - 95% coverage of medical, dental, and vision - Fantastic benefits, including: - $250 WFH setup (one time) - $500/year Learning & Development Benefit - $150/month cell phone + internet - $100/month Wellness - $100/month Co-working and Commuter Benefit - Several team onsites a year - Flexible PTO

• Manage a portfolio of SMB and/or mid-market clients through all stages of the customer lifecycle, from onboarding to ongoing success planning • Drive admin platform education and adoption by providing regular check-ins, product training, and best practice guidance • Identify growth opportunities within your accounts and collaborate with sales on upsell and expansion strategies • Monitor customer health metrics and proactively address at-risk accounts • Gather and communicate customer feedback to product and engineering teams to help shape our roadmap • Develop scalable processes and resources tailored to the unique needs of SMB clients

• Own end-to-end implementations for a portfolio of 5–7 enterprise and strategic customers, from kickoff through go-live and handoff • Act as the primary point of contact for customer stakeholders, including senior and executive-level partners • Develop and manage detailed project plans, timelines, and deliverables across complex, multi-workstream implementations • Drive cross-functional alignment across internal teams (Product, Engineering, Customer Success, Operations, etc.) to ensure successful execution • Proactively identify and mitigate risks, managing escalations with urgency and clarity • Lead effective, structured communication with both internal and external stakeholders, including regular status updates and executive readouts • Ensure a high-quality customer experience, balancing speed with accuracy and attention to detail • Continuously improve implementation processes by identifying patterns, gaps, and opportunities for scalability • Serve as a trusted advisor to customers, guiding them through best practices and complex decision-making

• Build, operationalize, and scale the security engineering practices that protect the benefits platform • Work across application security, cloud security, security architecture, supply chain security, detection engineering, and vulnerability management • Partner deeply with the teams building web and mobile applications, backend services, system integrations, card and banking workflows, infrastructure as code, and data platforms • Turn risk reduction into scalable guardrails, automated controls, and clear engineering guidance • Help define secure AI tooling usage, LLM and code-assistant governance, and data protection practices for AI-enabled development workflows • Balance ideal security outcomes with engineering velocity and business priorities

• Maintain and improve information security policies, standards, procedures, control documentation, and related governance materials. • Help map policies and controls to frameworks such as SOC 2, ISO 27001/27002, HITRUST, NIST CSF 2.0, and other customer, regulatory, or security requirements. • Support policy exceptions, risk acceptances, remediation tracking, control owner follow-ups, and recurring governance workflows. • Support SOC 2, ISO 27001, and HITRUST readiness, audit preparation, evidence collection, auditor coordination, and audit response management. • Maintain recurring evidence-gathering and control testing workflows, helping ensure controls operate consistently across the business. • Track audit findings, control gaps, remediation plans, owners, due dates, and closure evidence. • Support risk assessments, control gap assessments, internal reviews, and maintenance of the risk register. • Translate technical and security risks into clear business language, including mitigations, ownership, timelines, and residual risk. • Own or support customer security questionnaires, RFP security sections, due diligence requests, and trust or compliance documentation. • Maintain reusable questionnaire content, approved responses, compliance artifacts, and customer-facing assurance materials. • Support employee security awareness programs and create clear internal guidance for policies, controls, and compliance responsibilities. • Support vendor security reviews, third-party risk assessments, remediation tracking, risk acceptance documentation, and vendor compliance evidence. • Use GRC platforms such as Vanta, Drata, Thoropass, Secureframe, or similar tools to improve evidence collection, control monitoring, task tracking, reporting, and repeatable compliance operations.

• Design and operate systems responsible for ledgering, transaction processing, decisioning, and money movement • Build systems that are correct by design • Own the lifecycle of financial transactions end-to-end • Lead architectural decisions and write technical approach documents • Improve system resilience and operational tooling • Mentor other engineers

• Own Benepass’ fintech stack strategy, including build vs. partner decisions, across multiple time horizons • Manage and deepen relationships with key partners • Ensure existing integrations are stable, scalable, and fully utilized • Identify gaps in current capabilities and drive solutions with partners or internal teams • Align partner capabilities with our product roadmap and influence roadmap decisions • Evaluate and onboard new partners to expand our product offering • Act as the primary point of contact for fintech partners across product, engineering, and executive stakeholders • Lead issue resolution, escalations, and ongoing optimization work with partners • Represent Benepass in partner conversations and industry events

• Own launch readiness end-to-end • Drive launch readiness across all product and engineering workstreams • Build and manage project plans, timelines, and milestones, working backward from launch • Define readiness criteria and make final go / no-go recommendations • Run a weekly launch readiness sync to track progress, surface risks, and drive accountability • Identify downstream impact of product launches on Operations workflows, and ensure associated documentation and process updates are made • Monitor post-launch feedback, ensuring issues are resolved, and learnings are captured • Collaborate closely with our existing Operations Enablement function • Work directly with Product and Engineering Managers to understand the roadmap and upcoming sprint work • Evaluate initiatives for user, administrative, and internal operational impact, including potential effects on support volume • Translate technical work into clear operational implications and requirements • Ensure operational considerations are incorporated early in planning, not just at launch • Own a consolidated Ops roadmap across CX, CS, Implementation, and TAM, bringing a single, clear view of priorities • Build a structured system to synthesize Ops asks into clearly defined problem statements, and use cases • Quantify impact (revenue, retention, efficiency, risk) and help size opportunities to support prioritization (role needs to be analytical, and use Ops data - CX ticket data, Ops costs etc, - to drive clear prioritization) • Act as the single threaded owner of Ops → Product alignment, driving clarity on tradeoffs, sequencing, and expected business outcomes • Create launch runbooks that will enable scalable go-live plans as the company grows