Andrew Dwyer

Director of Customer Success at Five9

Greater Chicago Area

About

Dynamic Customer Success Leader with over a decade of experience in the SaaS industry, specializing in guiding Fortune 500 enterprises to achieve their strategic objectives for Digital Transformation. At Sprinklr, as Area Director of Customer Success, I led a high-performing team of 8 Customer Success Managers, overseeing a $60M book of business. I spearheaded initiatives that resulted in a 25% year-over-year growth, including negotiating a landmark 4-year, $65M contract—the largest renewal in Sprinklr's history. Operated as the Global Success Liaison for quarterly product releases, I collaborated closely with Product and Engineering teams to align the product roadmap with client needs, establish new processes & ensuring seamless integration and adoption. My strategic approach focuses on delivering measurable value, fostering long-term partnerships, and driving customer-centric innovation. I am passionate about empowering teams to excel, cultivating strong executive relationships, and leveraging data-driven insights to inform decision-making. My goal is to continue driving customer success initiatives that not only meet but exceed client expectations, contributing to both customer satisfaction and company growth.

Experience

  • Director, Customer Success at Five9
    Apr 2025 - Present · 1 yr 4 mos

    Led the transformation of Five9’s Customer Success organization by designing and operationalizing a more mature, scalable success program aligned to enterprise GTM objectives. Built and implemented standardized Success Planning, Renewal Readiness, and account health frameworks to improve predictability, executive alignment, and retention outcomes. Modernized the Customer Success go-to-market model by clarifying ownership across Sales, Success, and Renewals, driving tighter collaboration and unified account strategies. Developed capacity and segmentation models incorporating ACV, complexity, and customer footprint to optimize coverage, workload distribution, and growth focus.

  • Sprinklr (Chicago, Illinois, United States)
    • Area Director of Customer Success
      Dec 2023 - Apr 2025 · 1 yr 5 mos

      - Led & scaled a global Customer Success team of 8 CSMs - managing a $200M Book of Business across enterprise accounts. - Fostered a high-performance culture by designing a structured Performance Feedback Management System, enabling continuous skill development and driving measurable improvements in team performance. - Strengthened multi-threaded executive relationships - partnering with Directors, VPs, and C-Suite leaders to expand customer engagement and drive long-term retention and growth strategies. - Drove operational excellence by maintaining ELT alignment on Quarterly Renewal Forecasting & Retention, ensuring leadership had clear visibility into pipeline health and risk mitigation strategies. - Exceeded NARR retention goals - consistently surpassing the 90% target for four consecutive quarters, ensuring sustained revenue stability and customer satisfaction while mitigating churn through save plays. - Accelerated revenue expansion, increasing contract value by 15% in FY25 through strategic cross-selling, value realization programs, and product adoption initiatives. - Built a high-performing team hiring 4 new CSMs to strengthen CSM org, mentored & promoting 2 individuals into expanded leadership roles. - Championed strategic customer programs - collaborating with Product & Engineering teams to align Sprinklr’s roadmap with enterprise customer needs, ensuring high adoption and long-term retention.

    • Customer Success Director
      Apr 2022 - Dec 2023 · 1 yr 9 mos

      - Negotiated a 4-Year / $65M contract with 25% YoY growth - Managed Sprinklr's largest customer with an ecosystem of 50 IC’s + 1,000 hrs/mo of Prof Services - Acted as Global Liaison for Success Organization for Quarterly Product Releases - Collaborated with Product/Engineering for Technical API & Workflow Management for customer solutions - Prepared & Delivered EBR’s to Senior Level Execs focused on Value and Strategic Outcomes

  • Customer Success Manager at Sprinklr
    2020 - 2022 · 2 yrs

    Oversaw $5M book of business supporting Proctor & Gamble - Over my tenure I grew the account by 30% through up-selling new BU’s. Deployed a New Product “Media Insights” globally for 500 users and created new processes for newsletter distribution & analytics report delivery. Established new processes within Global Success Org to increase efficiencies, standardize the Success Engagement Process & improve customer happiness. Partnered with Sales / Solutions Consulting / Product / Engineering / Managed Services to execute customer requirements for partnership growth. Prepared & Delivered Executive Business Reviews to Senior Level Execs focused on value realization, product adoption, strategic roadmaps. Executed the Success Engagement Process through creation of success plans, adoption/consumption reporting, value realization, use case mapping. Global Success Liaison for Quarterly Product Releases - establishing new processes for field communication and increase efficiency cross functionally. Technical API & Workflow Management - managing platform integrations for data lakes, privacy & security requirements. Established a ESG Sustainability Program - built Sprinklr’s Sustainability program from scratch leveraging cross functional resources to deployment.

  • Vibes (2 yrs 3 mos)
    • Senior Customer Success Manager
      Jul 2019 - Mar 2020 · 9 mos

      - Oversee and establish direct relationships with 15 accounts across retail, restaurant & dining and healthcare with over $4M in annual contract revenue - Lead, manage and develop mobile strategy for all customers - Identify & close upsell opportunities to reach and exceed quarterly upsell targets and drive customer ROI - Conduct quarterly and annual forecasting and revenue planning for entire book of business - Ensure success plans, goals & KPIs have been established, tracked and met for each account - Hold internal and external Quarterly Business Reviews with a focus on customer relationship building and driving additional product adoption and revenue

    • Customer Success Manager
      Jan 2018 - Mar 2020 · 2 yrs 3 mos

      Serve as the key client contact by providing insight on mobile strategy, building concepts and implementing mobile marketing campaigns. Manage a 3m+ client portfolio. Proactively contribute actionable solutions to client goals and KPI's by identifying new opportunities for mobile landscape. Be the Mobile expert and Implement Vibes best practices, set up campaigns, monitor the results in real time and share robust reports for actionable results.

  • Account Director at TMP Worldwide
    Aug 2016 - Dec 2017 · 1 yr 5 mos

    - Leads and manages account team to implement strategic project plans for a $2.0M revenue book of business - Consults with the client in the strategic development of employer brand recruitment initiatives for Fortune 500 companies across the CPG, Healthcare, Fashion and Technology industries - Develops annual account plans and employer brand strategy through content marketing, digital branding, online advertising and digital marketing campaigns - Increased organic growth by 7% in $200,000 of proprietary software sales - Manages monthly forecasting and budget tracking to support my region in meeting quarterly revenue goals via Salesforce - Partners with consumer advertising and media agencies across global networks to deliver holistic and efficient Recruitment Marketing campaigns