Role Description Cover Whale is looking for a motivated, client-focused Agency Success Associate to support the growth of our agency partner network. Reporting to the Director of GTM, you'll be an integral part of the Growth team — helping manage the onboarding and activation of new agency partners from initial evaluation through their first steps with Cover Whale. In this role, you will work closely with the Agency Success Lead to support new agency partners through the appointment process, train them on underwriting guidelines, and ensure all documentation and licensing are complete. Gain comprehensive knowledge of the agency success function through cross-training, positioning yourself for long-term growth. This is a great fit for someone who enjoys working with clients and is eager to develop their skills in sales and revenue operations. You'll collaborate across teams, build hands-on experience with business development workflows, and grow in a fast-paced, supportive environment. For the right candidate, this role is a strong stepping stone toward a career in business development or sales operations. - Agency Engagement: Serve as the first point of contact for agencies seeking appointments with Cover Whale, providing timely responses to move prospects efficiently through the appointment pipeline. Engage with prospective agencies to understand their goals and identify opportunities to align them with Cover Whale's offerings. - Onboarding & Training: Guide new agency partners through the onboarding process, ensuring a smooth transition from appointment to active writing. Develop and maintain resources, guides, and tutorials that help agencies get up to speed quickly and adopt Cover Whale's platform confidently. - Platform Adoption & Support: Assist new and existing agents in navigating Cover Whale's platform and proactively surface recommendations to improve their experience. Support agencies in understanding Cover Whale's underwriting appetite to set them up for long-term success. - Data & Reporting: Track and monitor agency activation metrics, sharing insights with the Business Development team to improve onboarding and retention outcomes. Identify patterns in agency interactions and flag opportunities for process or product improvements. - Cross-Functional Collaboration: Partner with the Agency Success Lead, sales, underwriting, product, and marketing teams to ensure a seamless experience for agency partners. Serve as an internal advocate for agency feedback, helping shape improvements to Cover Whale's products, services, and processes. - Growth & Development: Cross-train with the Agency Success Lead to develop a full understanding of agency success workflows, systems, and strategy, ensuring continuity and building a foundation for career advancement. Qualifications - 1–3 years of experience in customer success, client services, sales support, or a related role. - Insurance industry experience is a plus, but not required. - Familiarity with the insurance or MGA space, particularly commercial auto (trucking, logistics), is a plus. - A bachelor's degree is nice to have. - Strong organizational skills with the ability to manage multiple priorities simultaneously. - Clear written and verbal communication skills; comfortable engaging and building relationships with external partners. - Working knowledge of tools such as Google Sheets, HubSpot, and DocuSign. - Analytical mindset with an interest in data-driven decision-making and process improvement. - Exposure to data analytics tools (Excel, SQL) or data visualization is a plus. Benefits - Annual discretionary bonus opportunity. - Comprehensive health, dental, and vision insurance. - 401(k) company match up to 4%. - Generous paid time off and company holidays.

• Drive adoption and outcomes • Build and run success plans tied to customer goals, milestones, and measurable outcomes • Establish a repeatable operating cadence that keeps onboarding and adoption moving • Monitor engagement and usage signals to proactively remove friction and drive progress • Deliver QBRs and EBRs that connect Harness usage to customer outcomes • Produce crisp BVR style recaps that document value delivered, risks, and next steps • Maintain stakeholder alignment across technical and executive audiences • Maintain clear renewal status, timeline, and risk posture across your portfolio • Surface risk early and coordinate action plans to keep customers on track • Partner closely with Sales to ensure renewals are proactive, clean, and value backed • Drive clear ownership and follow through on customer action items and escalations • Keep customer records accurate and current in Salesforce and Gainsight • Coordinate cross functional resources to unblock customers and stabilize outcomes

Role Description The Senior Manager of CS Enablement owns a meaningful portion of the CS program portfolio. This is not a support role. You will identify what CSMs and Account Managers need to do differently to retain and grow their accounts, build programs that address those gaps, deliver them, and track whether they worked. This role sits close to the field. You will attend CS leadership meetings, review Gong calls, shadow account reviews, and stay near enough to the post-sale motion that your programs reflect real account dynamics, not a textbook version of what good CS looks like. CS enablement requires a different instinct than Sales enablement. The buying decision is already made. Your programs need to help CSMs drive adoption, manage executive relationships, identify expansion signals, and recover at-risk accounts, all with buyers who are often overextended and skeptical of additional asks on their time. Candidates who have done that job before coming into enablement will bring a credibility advantage that is difficult to replicate. What you’ll do - Own the strategy and execution of Customer Success enablement programs end-to-end, from identifying field needs through launch, reinforcement, and measurement. - Build practical, high-impact learning experiences that help Customer Success teams improve performance in real customer conversations, not just complete training. - Create reinforcement systems that drive adoption after the session ends, including manager coaching frameworks, workflow tools, peer learning, and structured practice. - Manage multiple enablement initiatives simultaneously with strong operational discipline, clear prioritization, and consistent communication across stakeholders. - Stay deeply connected to the business by participating in team meetings, account reviews, and QBR prep sessions while leveraging Gong and Salesforce insights to identify trends, risks, and skill gaps. - Develop scalable, field-ready content that supports Customer Success Managers in renewals, expansion opportunities, executive business reviews, and customer recovery moments. - Partner closely with Customer Success leadership and frontline managers to embed enablement into team operating rhythms, coaching cadences, and day-to-day execution. - Design and facilitate coaching programs, role-plays, and scenario-based learning that help Customer Success teams build confidence, sharpen account strategy, and improve customer outcomes. What success looks like - NRR trend in the assigned segment following program delivery, compared to pre-program baseline. - Expansion conversion: Upsell and cross-sell attach rate in the assigned segment, as a proxy for expansion motion program effectiveness. - Percentage of accounts in assigned segment receiving a structured EBR on schedule, as a leading indicator of program impact on executive relationship quality. - Highspot engagement rate on assets produced, as a measure of whether field content is actually reaching and being used. - CS front-line manager rating of enablement support quality, collected quarterly. Qualifications - 7+ years in CS Enablement, Sales Enablement, or a post-sale revenue role with direct ownership of program design and delivery. - Experience in programmatic advertising, Connected TV, digital media, or a closely adjacent AdTech environment. - Fluency in CS methodology: value realization, EBR/QBR frameworks, expansion motion, at-risk account management. - Working knowledge of MEDDICC as an account health framework. - Strong facilitation skills — able to lead experienced CSMs with content that is immediately credible, practical, and grounded in real customer situations. - Proficiency in Gong, Salesforce, WorkRamp, and Highspot. Requirements - Direct experience as a CSM, Onboarding Specialist, or Account Manager in an AdTech, CTV, or SaaS environment before moving into an enablement function. - Familiarity with CTV-specific customer conversations: campaign performance reviews, attribution methodology, incremental reach, and renewal justification in a performance-driven buying environment. - Experience building programs for both CSM and AM roles simultaneously, accounting for the different renewal and expansion motions each role runs. - Experience using Gong data independently to build a picture of CS skill health. Benefits - 100% remote within the US. - Flexible vacation policy. - Annual vacation allowance for travel related expenses. - Three-day weekend every month of the year. - Competitive compensation. - 100% healthcare coverage. - 401k plan. - Flexible Spending Account (FSA) for dependent, medical, and dental care. - Access to coaching, therapy, and professional development.

• Administrative Management: Manage the lifecycle of Global Account paperwork, including contract amendments, renewals, cancellations, and transfers. • Cross-Functional Coordination: Collaborate with Billing and Sales to resolve payment disputes, credit memo requests, and debt collection inquiries for Global Accounts. • Data & Reporting: Produce and audit recurring performance reports for Strategic CSMs to share during Executive Business Reviews (EBRs). • Alignment: Participate in daily APAC CS stand-ups to ensure regional alignment and track the status of global task requests. • Project Management: Lead the implementation of contracted Revinate products (specifically Guest Feedback) for APAC customers. • Technical Launch: Coordinate with customers and internal technical teams to ensure integrations are completed on time. • Queue Management: Own and respond to Level 1 customer inquiries via Zendesk, maintaining high visibility and responsiveness. • Troubleshooting: Solve non-standard requests and troubleshoot web-related issues (browser settings, email rendering, etc.) before escalating complex bugs to Engineering. • System Integrity: Track and log all customer issues in Salesforce to maintain a "source of truth" for the global team.