Title: Customer Success Specialist Location: remote Remote, ., Canada . full-time Job Description: About Proposify At Proposify, we're revolutionizing the way businesses create and manage proposals. Our innovative platform streamlines the proposal process, helping teams craft compelling, professional proposals that close deals faster and with greater success. We pride ourselves on fostering a dynamic, inclusive, and collaborative work environment where creativity and innovation thrive. As we continue to grow and enhance our offerings, we are looking for talented individuals who are passionate about technology and driven by the challenge of making complex processes simple and efficient. Join us and be a part of shaping the future of proposal management! About the Role We, at Proposify, are passionate about helping sales teams win with better proposals. Our Customer Support Specialists are the frontline heroes, delivering first-class service experiences that help our customers thrive. As a core part of the Customer Success team, you’ll provide responsive, insightful support, assist with onboarding and technical troubleshooting, and collaborate cross-functionally to ensure seamless customer journeys. Your goal: help customers get the most out of Proposify by offering fast, friendly, and effective solutions. ***This is a remote position. To support collaboration with our team, candidates must be able to align their work hours with Pacific Time (PST).*** What You'll Do And Love Doing Customer Support & Ticket Management - Manage the daily support queue in Zendesk, responding to customer inquiries with fast, helpful solutions. - Resolve issues across billing, product, and technical topics with clarity and care. - Process billing-related items including refunds, credits, and invoicing nuances. - Participate in customer conversations as needed. Technical & Integration Support - Troubleshoot integration and API-related issues, including basic debugging using tools like Datadog. - Join customer, sales, or CSM calls to provide deeper technical insight when needed. - Support backend tasks such as ticket routing, SLA segmentation, and Zendesk reporting on a rotating basis. Customer & Internal Training - Deliver onboarding sessions to customers as part of sold training packages - Contribute to internal training, including onboarding new team members and educating on new systems or workflows. Process & Content Enablement - Maintain and contribute to the knowledge base with articles, videos, and helpful self-serve content. - Participate in workflow optimization projects to enhance both customer and team efficiency. - Help manage and enhance the CS Bot to improve self-service and ticket deflection. What We'll Love About You - You have 1–3 years in a customer support, technical support, or SaaS customer success environment. - Proficiency in Zendesk (or similar support platforms), and familiarity with CRM tools. - Clear, empathetic communicator with a knack for simplifying complex topics. - Technical curiosity—comfortable learning how integrations work and explaining them to others. - A team mindset—you thrive in a collaborative, fast-paced environment where everyone pitches in. What You'll Love About Us While Proposify world headquarters is in Halifax, Nova Scotia, we are a 100% remote company with employees working from all over the world. We’ve invested in all of the systems and tools that make remote work enjoyable, productive, and connected. People feel empowered to do their best work and test out ideas. They don’t just ask ‘Why?’ but try ‘Why not?’ We are a team that embraces the new, the maybe, the unknown because we know that’s where growth lies; just beyond our comfort zone, just beyond what the experts say, and way beyond the way- we’ve-always-done-things. Everyone is a leader in their role and has the autonomy and responsibility to contribute, to change, and to challenge. We don’t care how many hours people work, we care about the quality and impact of their work. We get shit done. We get shit done fast. We are not a static company; we are moving forward and continually evolving to make things better for our business and the businesses of our customers. We have flex hours so employees can design their day to work when they’re most productive, and allow for time each day to spend with family and friends, take advantage of nice weather, focus on wellness, and pursue their hobbies and passions. Some Of Our Benefits Include - Competitive market based salaries - Company provided and paid health benefits from the day you start, paid entirely by Proposify - Virtual Health Care - RRSP matching program from the day you start with no vesting period - Generous Paid Time Off Policy including: 3 weeks of vacation to start; paid sick leave; personal days; birthday leave, company-wide end-of-year holiday break - Skills Training Enrichment Program to grow your knowledge and skills within your role - Brightpass (free online fitness and wellness courses) - Flexible working hours so you can do your best work when you are at your best - WFH Stipend setting you up for success! At Proposify, we value and celebrate the diversity of our team and welcome applications from racially visible persons, Indigenous peoples, women in non-traditional positions, persons with disabilities, and persons of the LGBTQ+ community.

Role Description As part of the Customer Success and Engineering organization, you will be the primary technical owner of the post-sale relationship for our most strategic accounts. While the Solutions Architect designs the vision, you ensure that vision becomes a reality. You will act as a long-term trusted advisor and the "glue" between the Customer’s technical team, our Support team, and our Forward Deployed Engineers (FDEs). - Orchestrate Technical Delivery: Serve as the primary technical point of contact post-sale, coordinating efforts between Solutions Architects, Forward Deployed Engineers, and Support to ensure seamless project execution. - Drive Adoption & Value: Guide customers through the implementation lifecycle, ensuring they effectively utilize Vector Search to solve their specific real-world problems and achieve their business goals. - Project & Stakeholder Alignment: Manage expectations across multiple customer projects. You will map customer timelines to internal engineering resources and ensure alignment between client stakeholders and our technical teams. - Technical Health Oversight: Conduct regular technical health checks and architecture reviews to identify bottlenecks, suggest optimizations, and maximize usage of the product. - Feedback Loop: Act as the strategic voice of the customer. Aggregate technical feedback and friction points from the field to help shape and prioritize the Engineering and Product roadmap. - Crisis Management: Serve as the escalation manager for critical technical issues, mobilizing Support and Engineering resources to resolve blockers in high-stakes deployments. - Evangelize Best Practices: Educate customers on the optimal patterns for building Agentic AI and RAG solutions, moving them from initial use cases to enterprise-wide adoption. Qualifications - 3+ years of experience in a customer-facing technical delivery role. - Proven ability to manage complex, multi-stakeholder technical projects and keep them on track without direct authority. - Understanding of the ML lifecycle, data pipelines, and the fundamental concepts of search/retrieval systems. - Ability to translate complex technical blockers into business impact for executives, while also talking shop with developers. Requirements - Experience with Kubernetes and Cloud-native ecosystems (AWS, GCP, Azure). - Experience with Search technologies (Elasticsearch, Solr, Pinecone, Milvus, or Qdrant). - Background in working with "Forward Deployed" or "Professional Services" models. Benefits - A remote-first, international team working on cutting-edge AI infrastructure. - A competitive salary with additional perks. - Flexible working hours and async-friendly culture. - High ownership and real impact. - Open-source, engineering-driven culture. - Choose your own laptop equipment. - For US-based candidates, a comprehensive benefits package including 401k match, health, dental, and vision insurance, plus flexible PTO policy.

Role Description The Regional Owner Success Lead will manage a team of Coordinators on our Hawaii team. The ideal candidate has the ability to lead a team of coordinators that provides exceptional customer service while balancing empathy and accountability during demanding times. This role requires effective communication, analytical thinking, and problem-solving skills along with the ability to adapt to and lead change. The role is responsible for continued education and up-to-date knowledge of our products, programs, and services. Essential Job Functions - Oversee daily operations and workflow management to optimize team productivity and meet departmental objectives. - Identify areas for improvement, and implement process enhancements to drive efficiency and quality outcomes. - Lead and develop a team of Owner Success Coordinators through effective coaching, mentoring, and performance management. - Conduct regular one-on-one meetings and annual evaluations to support professional growth and ensure alignment with company goals. - Audit team’s work for quality of support, accuracy of information provided to owners, and delivery tone. - Provide guidance and support to team members in handling challenging situations and resolving homeowner concerns. - Set clear performance goals and expectations for team members, and conduct regular performance reviews. - Conduct disciplinary action as needed, including informal and formal write-ups and corrective action plans to improve performance. - Monitor, analyze, and evaluate trends in volume and workload against performance. - Manage and monitor the team’s schedule. - Understand higher-level business goals and our department’s role and impact. - Manage staffing in relation to daily contacts in a multi-channel in- and outbound contact center, focusing on meeting performance metrics and exceeding customer expectations. - Ensure employee adherence to company values, quality, accuracy, schedule, and other expectations in a fast-paced environment. - Build and maintain business relationships and open lines of communication with other internal support teams. - Foster a collaborative work environment that promotes open communication, innovation, and employee engagement. - Address team conflicts constructively and in a timely manner as they arise. - Assist the recruiting process with interviewing, selection and onboarding new team members while ensuring compliance with company policies and employment regulations. - Other duties as assigned because every day is different in hospitality! Qualifications - Experience working in hotel, hospitality, vacation or similar industry is highly preferred. - 1-2 years of experience in a direct supervisory or management level position in a similar industry. - 3-5 years of customer service/call center experience. - Tech-savvy with experience using various digital systems and applications and comfortable using mobile apps, tablets, and various software platforms. - Experience managing day-to-day team operations, providing guidance and support, and fostering a positive, productive team culture focused on collaboration, accountability, and growth. - Demonstrated ability to multi-task, prioritize, and remain organized in a fast-paced and constantly changing work environment. - Embrace and lead change. - Problem solve with limited direction and support, implementing innovative solutions. - Review and analyze information to identify trends and propose solutions. - Dependable and prepared. Showing up on time and ready to go is key to creating great stays for our guests and peace of mind for our homeowners. - Must be dependable, self-motivated, and able to work independently while contributing positively to a collaborative team environment. - Comfortable talking to people—online or in person—and being able to share information in a way that’s clear, thoughtful, and represents the company in a positive way always. Workplace Environment + Physical Requirements - Fully remote work environment with reliable internet connection. - Speed test required: please use this link to run the internet speed test. The internet speed must be at least 100.0 download/10.0 upload. If your internet does not meet these requirements, you will need to upgrade prior to applying. - We’re in hospitality and our schedules can change based on guest and homeowner needs. Shifts may include early mornings, evenings, weekends, and holidays. We require flexibility to support this. - Typically a Monday - Friday workweek with expectations to be flexible to support the needs of the business. - You’ll be working in your home office setting. This position requires frequent, repetitive use of a computer, phone, and office equipment. - This position requires patient, professional communication with prospective clients, and the ability to build confidence with prospects. - Ability to move freely (balancing, climbing, crawling, driving, squatting, standing, stooping, walking, bending, pushing, pulling, reaching, and repetitive hand/finger motions) and lift up to a maximum of twenty-five (25) pounds without assistance. Benefits - Health/dental/vision insurance based on hours worked. - Employer Sponsored & Voluntary Supplemental Benefits based on hours worked. - 401K retirement savings plan with immediate 100% company match on the first 4% you contribute. - Health & Dependent Care Flexible Spending Accounts based on hours worked. - Paid Flex Time Off. - Employee Assistance Program (EAP). - Employee Discounts.

Your role at Dynatrace - Constantly go above and beyond to serve our customers and be a shining, standard-setting example of our Core Values. - Triage, diagnose, and provide solutions to most complex configuration issues with Dynatrace solutions and non-Dynatrace integrations. - Strategize on the overall technical objectives and long-term goals of the team. - Provide advice and guidance as the subject matter expert to ensure successful ongoing usage, adoption of the product, and foster growth of the customer’s footprint. - Be the customer’s advocate by knowing their goals and use cases, then suggesting process improvements, product adoption, configuration, and additional features to meet their requirements. - Provide web-based training to user groups to support organizational adoption. - Undertake discovery and education activities to identify opportunities for Dynatrace usage across organizational functions and processes. - Providing coaching to TAMs to help them grow in their technical knowledge and personally. - Function as a frontline technical resource for “best practice” and informal customer questions. - Engage with customer support as a customer advocate to ensure speedy resolution of customer issues - Engage with Product management as the customer advocate on product roadmap discussions. - Participate and prepare for Monthly and Quarterly Business Reviews with customers. - Maintain current functional and technical knowledge of Dynatrace products and services. - Help to document best practices in developing and using Dynatrace Partner with support engineers, PM, and R&D to help customers and account teams to speed resolution. - Help communicate, escalate and advocate on behalf of the customer. - Provide insights, advice, and ‘street credibility’ with technical teams to understand technical issues and possible workarounds. - Help customers and account teams to understand support ticket trends/themes to be used to develop success plans, enablement advice, etc. - Have deep understanding of customers’ infrastructure, architecture, and business/regulatory requirements to speed up resolution. What will help you succeedEducation: - Bachelor's degree in Computer Science, Information Technology, or equivalent work experience - Work experience 4+ years of experience - Experience working with large enterprise customers, including executive leadership - Demonstrated ability in leadership, mentorship, and organizational behavior - A track record of going above and beyond for your team and customers - Ability to manage executive relationships and discussions (VP/CxO) - Must have exceptional English written and verbal communications skills, as well as organizational and teamwork skills, and the ability to act fast and responsibly Impeccable time management skills and an ability to self-direct - Demonstrated experience being a Subject Matter Expert (SME) for Dynatrace technologies, methodologies, frameworks, and 3rd party technologies related to Dynatrace - Willingness to learn new technologies and resolve complex technical issues - Professional Level Dynatrace certification (or get certification within six months) - Two or more industry-relevant Associate Level certifications (AWS, Azure, k8s, …) - Strong technical understanding and experience in SaaS industry - Knowledge and experience with one or more of the following technologies related to Dynatrace: Cloud/new stack technologies such as OpenStack, OpenShift, AWS, Azure, Google Cloud, Cloud Foundry, Kubernetes, SAP, etc. - Web and application server technologies such as Apache, IIS, WebSphere, WebLogic, and JBoss Server/Server-side technologies such as Java Servlets, PHP, HTML, CSS, JavaScript, and Ajax - Mobile application technologies such as iOS and Android Webkit DevOps toolchain applications such as Ansible, Jenkins, Chef, Puppet, etc. - CMDB/ITSM Technologies/platforms such as ServiceNow and BMC - Must be customer service oriented and believe in teamwork, collaboration, adaptability & Initiative - Demonstrable success in thinking strategically and executing tactically while providing consistent and high customer satisfaction and retention levels in a fast-paced environment Why you will love being a Dynatracer - Dynatrace is a leader in unified observability and security. - We provide a culture of excellence with competitive compensation packages designed to recognize and reward performance. - Our employees work with the largest cloud providers, including AWS, Microsoft, and Google Cloud, and other leading partners worldwide to create strategic alliances. - The Dynatrace platform uses cutting-edge technologies, including our own Davis hypermodal AI, to help our customers modernize and automate cloud operations, deliver software faster and more securely, and enable flawless digital experiences. - Over 50% of the Fortune 100 companies are current customers of Dynatrace. Compensation and Rewards