Roadie

• Identify, thoroughly investigate, and resolve risk-related issues on the Roadie platform • Leverage data to identify patterns and trends in escalated incidents • Identify procedural gaps to develop efficiency and effectiveness within the team • Manage critical and high-risk situations appropriately and with a sense of urgency • Adjudicate user background screenings while adhering to geographic compliance & regulations • Adhere to legal and risk-related policies and procedures • Partner with law enforcement as needed when managing ongoing investigations • Investigate, audit, and decision on sender Gig related claims • Research industry standards and best practices to improve internal processes • Reduce company losses by assessing internal and external liabilities • Partner with the Legal team to conduct investigative research and support external user communications

• Own the roadmap and backlog for Roadie’s internal billing and sender payment platforms, balancing business priorities, technical needs, and long-term product strategy • Partner with Finance, Sales, Data Science, Operations, and Engineering to design and deliver scalable billing and payment solutions • Translate complex business needs into clear product requirements, user stories, and prioritized work for engineering teams • Drive product decisions by analyzing data, identifying opportunities, and measuring the impact of new features and improvements • Build and maintain strong relationships with internal stakeholders and external partners, including UPS and payment vendors • Develop reporting and instrumentation to monitor billing accuracy, platform health, and operational performance • Continuously improve internal workflows to increase efficiency, reduce manual effort, and create a better experience for Roadie teams

Role Description As a CX Content Specialist, you will play a critical role in developing, organizing, and maintaining high-quality internal and external content that supports the Customer Experience (CX) team, our customers, and cross-functional partners. You will work closely with Training, Quality, and Operations teams, as well as collaborate with Product, Marketing, and Legal stakeholders to ensure content is accurate, consistent, and aligned with brand standards. You will be responsible for managing content requests, maintaining our knowledge bases, and ensuring content enables CX teams to deliver a seamless customer experience. What You’ll Do - Create and refine CX content that aligns with Roadie’s voice and style, ensuring clarity, consistency, usability, and strong customer self-service outcomes. - Regularly audit internal and external Salesforce content for accuracy and relevance, partnering with the CX Enablement team to analyze user behavior, address content gaps, and improve resources. - Translate process maps and workflows provided by CX Operations Specialists into clear, digestible guides for CX team members. - Partner with Product and Marketing teams to stay current on feature rollouts, enhancements, and campaigns, ensuring CX teams are equipped with the most up-to-date resources and messaging. - Work with the Legal team to secure necessary approvals for external-facing content. - Prioritize and organize incoming content requests based on scope, urgency, and deadlines. - Ensure efficient and timely completion of deliverables based on KPIs set by the Content & Instructional Design Manager. - Develop and maintain CX team macros to ensure standardized, brand-aligned communication across customer interactions. - Deliver and manage internal communications for CX teams across communication channels. - Optimize the knowledge base’s search experience by staying current on Salesforce features and capabilities. - Provide regular updates to CX Enablement leadership regarding help center performance, content initiatives, and identified opportunities for knowledge improvement. Qualifications - Bachelor's degree in English, Communication, Technical Writing or a related field. - 2+ years of experience in technical writing or content development and creation. - Experience with content management systems and knowledge bases, Salesforce strongly preferred. - Ability to quickly grasp technical knowledge and convey relevant information in an engaging manner. - Tenacity for problem-solving with exceptional patience and persistence. - Excellent written and verbal communication skills, with an ability to communicate technical concepts to a nontechnical audience. - Ability to produce digestible, searchable, accessible content for a variety of audiences. - Self-starter and ability to work independently. Benefits - Competitive total rewards package. - 100% company-paid health insurance for yourself. - 401(k) with company match. - Tuition & student loan repayment assistance - yes, we’ll contribute directly to your student loans! - Remote-first environment. - Unlimited PTO. - Inclusive family leave policy that supports all new parents. - Paid Wellness Days in addition to Company holidays. - Monthly WFH stipend. - Paid sabbatical leave - tenured Roadies are given extra time to unplug, rest, and explore. - The technology you need to get the job done.

• Own the end-to-end strategy and performance of Roadie’s third-party contact center vendors, ensuring alignment with Roadie’s CX goals • Lead and mentor CX Vendor Managers, driving accountability, performance, and effective escalation management • Drive comprehensive vendor assessments by analyzing performance data, KPIs, compliance, quality, and service levels • Monitor and manage vendor performance, holding partners accountable to Roadie’s service delivery and quality expectations • Identify opportunities for operational improvements and guide your team in building clear action plans to drive measurable results • Collaborate and align with Training & Quality to oversee initial and ongoing training and enablement requirements for all vendor partners. • Ensure adherence to contract terms, SLAs, commitments, and communication standards—escalating concerns when needed • Oversee and coordinate vendor performance audits (regulatory, technical, security, risk, etc.) and communicate insights to Roadie leadership • Build and maintain strong vendor relationships, including facilitating QBRs, participating in contract negotiations, and overseeing invoice review and approvals • Partner with Workforce Management to forecast capacity needs and allocate headcount across vendors • Collaborate cross-functionally to support broader CX operational initiatives and contribute to strategic planning • Owns risk management, including operational, contractual, and co-employment considerations

Role Description Our Support team is the front line of the Roadie experience, serving as the trusted first point of contact for our community. We’re looking for a Customer Support Specialist who thrives from helping people, brings strong communication and problem-solving skills, and genuinely puts the customer first. In this role, you’ll become an expert in our mobile and web-based tools, playing a critical part in keeping our logistics services running smoothly while delivering exceptional experiences to our users. This is a full-time role on a 4-day workweek, with schedules that may include evenings, weekends, and holidays—perfect for someone who enjoys flexibility and fast-paced, meaningful work. - Provide phone, email, and text-based support to Roadie customers, partners, users, and other community members - Address all customer concerns politely, using active listening skills to understand and confirm the information - Balance efficiency and speed in addressing questions or issues with ensuring a high-quality customer experience - Proactively monitor in-progress deliveries and take corrective action when necessary - Manage non-standard delivery situations with professionalism, empathy, and urgency - Effectively use Salesforce and other internal tools to accurately log interactions and solve issues - Collaborate with team members from various Roadie departments to ensure seamless delivery experience Qualifications - 2+ year customer service experience, optimally with a technology or logistics company - Strong written and verbal communication skills, with the ability to interact and connect with many types of personalities - Able to quickly and efficiently problem solve and troubleshoot - Comfortable with a fast-paced environment and changing requirements - Ability to receive and implement feedback to continuously improve quality of support provided to customers - Proactive and able to comfortably navigate through uncertainty and ambiguity - Must have the ability to work a schedule comprised of non-standard hours, including evenings and weekends - Experience with Salesforce, a plus! Benefits - Competitive total rewards package - 100% company-paid health insurance for yourself - 401(k) with company match - Tuition & student loan repayment assistance - yes, we’ll contribute directly to your student loans! - Remote-first environment - Generous PTO - Inclusive family leave policy that supports all new parents - Paid Wellness Days in addition to Company holidays - Monthly WFH stipend - Paid sabbatical leave - tenured Roadies are given extra time to unplug, rest, and explore - The technology you need to get the job done

• Contribute to and drive the strategic direction for Trust & Safety, translating team priorities and risk insights into measurable OKRs and operational roadmaps • Directly manage Trust & Safety Leads, coaching and developing them to build a high-performing, accountable organization with strong ownership of KPIs, quality, and service levels • Own end-to-end risk mitigation strategy across Critical Response, Compliance, and Claims, ensuring scalable, consistent, and defensible decision-making frameworks • Leverage data to identify trends, forecast emerging risks, drive operational improvements, delivering regular reporting to the Director and other stakeholders • Partner cross-functionally with Legal, Product, Engineering, Operations, and CX leadership to shape policy, influence product and technology decisions, and implement scalable risk mitigation solutions that support strategic Trust & Safety objectives and operational effectiveness • Drive operational scale and efficiency, identifying systemic gaps and leading initiatives across tooling, automation, and process optimization • Oversee high-severity incidents and escalations, ensuring executive visibility, clear communication, and effective resolution • Ensure compliance with legal and regulatory standards, proactively adapting to evolving requirements and minimizing organizational risk exposure • Champion a culture of sound judgment, accountability, and continuous improvement, raising the bar for decision quality and risk ownership across the team • Lead change management initiatives, guiding the department through process, policy, and structural evolution

• Help review and organize outdated or redundant project items within Jira and related tools • Support documentation efforts by updating process guides, templates, and team resources • Collaborate with team members to identify opportunities for improving project organization and workflow consistency • Assist with meeting coordination, note-taking, action item tracking, and follow-up communication • Help prepare project summaries, status updates, and internal documentation • Participate in PM and Scrum team meetings to gain exposure to Agile project management practices • Assist with creating and maintaining Jira dashboards, reports, and tracking systems to help support project visibility and organization • Support the Project Manager with day-to-day operational and coordination tasks

• Collaborate with CX stakeholders to conduct needs assessments, identify learning objectives and appropriate learning strategies for the CX team • Design, develop, and implement a variety of instructional materials, including digital learning materials, presentations, tutorials, videos, job aids, and other resources, using instructional design principles and best practices • Create interactive and engaging learning experiences that cater to diverse learning styles and preferences • Conduct learning evaluations to measure the effectiveness and impact of learning interventions, from reaction through results • Continuously iterate and improve upon instructional materials based on content feedback from facilitators, learnings and need analysis data • Stay abreast of industry trends and emerging technologies in instructional design and adult learning to inform the development of innovative learning solutions • Collaborate with external vendors and partners as needed to augment in-house expertise and resources • Provide guidance and support to internal teams and stakeholders on instructional design principles and best practices

• Work cross-functionally with the InfoSec, SRE, and Engineering teams • Keep up to date with current vulnerabilities in the DevOps space, patch, mitigate, or procure acceptance of the vulnerability by InfoSec standards • Check code and repositories for insecure coding practices and work with Engineering teams to remediate • Work closely with InfoSec to create and maintain Secure SDLC training • Conduct security based quality assurance on pre-deployment packages, and seek approval or denial of those deployments based upon security findings • Conduct security based quality assurance such as dynamic and static code testing • Work closely with Compliance and Engineering teams to conduct pre-project risk assessments • Implement security checks and practices within CI/CD pipelines to ensure secure code deployment and infrastructure • Develop automation scripts and tools to streamline security processes, including vulnerability scanning, patch management, and incident response • Conduct security training and awareness programs for engineering teams to promote a security-first culture

• Own and optimize the calendar for blogs and press releases, ensuring Roadie’s digital presence stays dynamic, timely, and engaging • Develop and launch strategic email programs that amplify thought leadership and drive meaningful audience engagement • Grow and elevate Roadie’s LinkedIn presence through compelling copy, thoughtful content scheduling, active social listening, and performance reporting tied to key metrics • Support ongoing website content enhancements to keep messaging fresh, relevant, and impactful • Plan, build, and execute integrated multi-channel campaigns that align with broader marketing goals and strengthen brand voice • Contribute to PR initiatives through proactive media monitoring and identifying opportunities to amplify brand visibility • Analyze campaign and program performance, uncover insights, and share wins and learnings that fuel future success