Gladly

• Support deal reviews for completeness, accuracy, and compliance before close, working alongside senior Finance teammates to ensure deals are structured correctly across pricing, discounting, and contract terms • Help manage the day-to-day quote-to-cash workflow in Salesforce: deal progression tracking, certification process management, renewals tracking, and pipeline reporting • Maintain a clean approval audit trail and deal log to support accurate pipeline reporting and downstream revenue recognition • Learn and apply pricing compliance guidelines, discount thresholds, and revenue recognition requirements (ASC 606) with increasing independence over time • Support the margin calculator used to evaluate pricing structures on enterprise deals, building comfort with how AI vs. Team margin dynamics affect deal economics • Flag friction points in the Deal Desk process and bring ideas for improvement to the team • Help support deal desk systems including DealHub (CPQ) and Salesforce, contributing to data integrity and process consistency under the guidance of the Systems Design team • Assist with configuring and optimizing deal desk tooling, including approval workflows, pricing rules, and quote templates • Help identify opportunities to automate recurring processes and reduce manual effort across the deal desk function • Show genuine curiosity about AI tools (Claude, ChatGPT, Copilot, or similar) and a willingness to learn how they can help you move faster and reduce the lift on repetitive tasks • Apply an automation-first lens to your own work: if you are doing something manually more than twice, start thinking about how to streamline it • Partner with the Finance team on identifying and implementing AI-assisted workflows across Deal Desk processes

• Lead Major AI & Automation Initiatives • Ship Real Products • Design Foundational Systems • Collaborate Closely • Drive Innovation

• Carry a net dollar retention quota. Own the full renewal cycle, proactively identify and close expansion and cross-sell opportunities, and drive adoption of Gladly’s AI products across your portfolio. • Build efficient account plans that balance high-impact strategic engagement with portfolio-wide coverage. Identify key accounts for deeper investment and develop playbooks for scalable growth. • Lead QBRs, renewal discussions, and strategic conversations with VP and Director-level stakeholders. Translate platform value into business outcomes that support retention and growth. • Manage renewal and expansion negotiations with confidence. Navigate procurement and approval processes efficiently across a larger book of business. • Leverage knowledge of Gladly’s platform and Customer AI capabilities to recommend solutions that drive efficiency and customer value. Position AI adoption as a strategic expansion lever. • Partner with Sales, Product, and CX teams to advocate for the Voice of the Customer and ensure alignment on account priorities and timelines.

• Carry a net dollar retention target across your portfolio. Own the full renewal cycle, drive cross-sell revenue through increasing AI product adoption, and proactively identify and close upsell revenue. • Build and execute comprehensive account plans that map white space, identify key stakeholders, and align Gladly’s platform with each customer’s strategic priorities and business outcomes. • Own all executive-level relationships and engagement. Lead Customer QBRs and EBRs independently, translating platform data into business outcomes that resonate with executive stakeholders ranging from CIOs, CTOs, CDOs, and COOs to VPs of CX (Support, Service, etc.), VPs of IT, and beyond. • Lead complex, multi-stakeholder renewal and expansion negotiations. Navigate procurement, legal, and executive approval processes with confidence and urgency. • Leverage deep knowledge of Gladly’s platform and Customer AI capabilities to recommend solutions that drive radical efficiency and customer devotion. Position Gladly’s AI products as strategic investments, not line items. • Partner closely with Sales, Product, and CX teams to ensure the Voice of the Customer shapes our roadmap. Hold internal and external stakeholders accountable to timelines and commitments.

• Partner with Account Executives as the technical lead across enterprise sales cycles, owning the solution strategy from discovery through close • Design and deliver custom demos, live product presentations, and business value analyses tailored to each prospect’s architecture and stakeholder priorities • Build proof-of-concept environments that integrate with customers’ existing tech stacks — registering APIs on the Gladly app platform, writing lightweight integrations in JavaScript and Node.js, and using Postman to troubleshoot API calls • Translate customer business requirements into AI-driven workflows, scoping integrations and articulating how the Gladly platform creates value beyond cost reduction • Serve as the competitive expert in head-to-head evaluations, clearly differentiating the Gladly approach to customer experience AI against incumbent and emerging platforms • Support expansion and AI upsell opportunities within the existing customer base, and rotate on select mid-market deals to broaden team coverage • Collaborate cross-functionally with Product, Engineering, and Implementation to relay customer feedback and ensure smooth post-sale handoffs

• Own the success of Gladly customers in achieving the value of relationship-based customer service using the Gladly platform. • Build lasting relationships through consistent engagement with customer executives and managers to instill understanding of product vision, value proposition and features. Proactively engage clients to drive product adoption and optimal product experiences. • Partner with Sales Account Executive to develop and execute on account plans, ensure alignment within Gladly teams on account strategy. Develop & maintain relationships with other key internal customer champions, including engineering, product and marketing leadership to help strategically guide the direction of the product based on voice of the customer feedback. • Serve as a product expert for customers, including deployment best practices as well as configuration of product settings/rules to address customer business and technical needs. • Act as a strategic advisor with the ability to make recommendations on how to best leverage the Gladly platform as well as improve processes that may fall outside of the contact center. • Resolve account issues quickly, leveraging resources from across the company as needed. • Contribute to Gladly's Customer Success program development, strategic planning, and customer engagement approach to drive consistency and scale as the company grows. • Participate in pre-sales activities with prospective customers such as meetings, workshops, and webinars.