[All remote jobs](https://jobicy.com/jobs.md)[![Ashby logo](https://jobicy.com/data/server-nyc0409/galaxy/mercury/2025/08/63864ee6-221.png)](https://jobicy.com/company/ashby.md)[Ashby](https://jobicy.com/company/ashby.md) # Senior Strategic Implementation Specialist – Americas Review the role, location requirements, compensation details, and application process before deciding whether this opportunity fits your next career move. [Apply for this job](#job-application)[View company](https://jobicy.com/company/ashby.md)ShareRemote from[USA](https://jobicy.com/job-region/usa.md), [Canada](https://jobicy.com/job-region/canada.md)SalaryUSD 170k–200k / yrDepartment[Project & Program Management](https://jobicy.com/categories/project-management.md)EmploymentFull TimeExperienceDirectorPublished23 Oct 2026Apply before22 Nov 2026Listing views49Application actions1Application toolkit ## Make your next move. Prepare your resume, explore your fit, and draft a cover letter for this opportunity. AI Summary ## The role, at a glance. Ashby is hiring a senior implementation specialist to lead end-to-end deployments for strategic, predominantly enterprise SaaS customers. The role sits within Professional Services and Customer Success, with responsibility for implementation planning, stakeholder alignment, milestone management, and accelerating customer time to value. The specialist will run multiple complex onboarding projects concurrently while maintaining a responsive, collaborative customer experience. This is a remote full-time position open to candidates in the United States and Canada, with travel capability required. ## Role DNA A quick view of the complexity, pace, ownership and collaboration implied by the job description. ### Job Complexity 4/5EasyHard ### Pace & Pressure 4/5RelaxedFast-paced ### Autonomy Level 4/5GuidedFull ownership ### Communication Load 5/5IndependentCollaborative AI insightThe position requires independently delivering several complex enterprise implementations at once while coordinating customer and internal stakeholders. Success depends on strong program control, consultative communication, and the ability to resolve issues without compromising delivery quality. ## Salary analysis Estimated compensation compared with the broader US market for similar roles. Estimated job median (per year)Highly competitive$185,000US market range (per year)$155k–$210k0$231.00k AI insightThe employer discloses a base compensation range of USD 170,000 to USD 200,000 per year, with a midpoint of USD 185,000. Estimated US market compensation for a senior enterprise SaaS implementation specialist is approximately USD 155,000 to USD 210,000 annually; this is an AI estimate, not verified salary research. ## Core skills Skills and capabilities most closely associated with this opportunity. [Enterprise SaaS implementation](https://jobicy.com/jobs?search_keywords=Enterprise%20SaaS%20implementation.md)[Project management](https://jobicy.com/jobs?search_keywords=Project%20management.md)[Customer onboarding](https://jobicy.com/jobs?search_keywords=Customer%20onboarding.md)[Customer success](https://jobicy.com/jobs?search_keywords=Customer%20success.md)[Stakeholder management](https://jobicy.com/jobs?search_keywords=Stakeholder%20management.md)[Implementation planning](https://jobicy.com/jobs?search_keywords=Implementation%20planning.md)[Milestone management](https://jobicy.com/jobs?search_keywords=Milestone%20management.md)[Cross-functional collaboration](https://jobicy.com/jobs?search_keywords=Cross-functional%20collaboration.md)[Change management](https://jobicy.com/jobs?search_keywords=Change%20management.md)[Risk management](https://jobicy.com/jobs?search_keywords=Risk%20management.md)[B2B SaaS](https://jobicy.com/jobs?search_keywords=B2B%20SaaS.md)[Remote collaboration](https://jobicy.com/jobs?search_keywords=Remote%20collaboration.md) Sample interview questionsHow do you structure an enterprise SaaS implementation from kickoff through go-live?I begin by confirming business outcomes, scope, stakeholders, dependencies, and success metrics. I translate these into a documented implementation plan with owners, milestones, risks, communication cadences, and acceptance criteria, then review progress regularly and adjust transparently when priorities change. Describe how you manage several complex implementations at the same time. I maintain a portfolio view that tracks milestones, customer health, risks, decisions, and capacity across each account. I prioritize work by customer impact and delivery risk, establish predictable operating rhythms, and escalate blockers early with clear options and ownership. What would you do if an enterprise customer is falling behind on implementation tasks? I would identify the root cause, such as unclear ownership, competing priorities, missing data, or a technical dependency. I would then align the customer and internal team on a revised recovery plan with specific owners and dates, while communicating any impact on the go-live timeline early. How do you ensure customers realize value quickly without sacrificing implementation quality? I focus first on the workflows and configurations that support the customer's highest-priority outcomes. I use a phased approach when appropriate, set clear readiness criteria, and pair efficient delivery with validation and enablement so the initial launch is both useful and sustainable. How do you communicate implementation risk to senior customer stakeholders? I present risks concisely in terms of business impact, timeline, likelihood, and recommended decisions. I avoid surprises by providing regular status updates, documenting dependencies, and bringing actionable mitigation options rather than simply escalating problems. Opportunity details ## About this role. ### Senior Strategic Implementation Specialist, Americas Hi! I’m Morgan, the Manager of Strategic Implementations here at Ashby. Our customers are at the center of everything we do, and that’s especially true during implementation. We take pride in being responsive, collaborative partners who focus not just on delivery, but on doing things thoughtfully. This role plays a critical part in ensuring our new customers start off with a strong foundation and a clear path forward. I’m thrilled to be hiring our next Implementation Specialist. As part of our growing Professional Services team within Ashby’s Customer Success organization, you’ll play a key role early in the customer journey—ultimately helping to elevate the entire customer experience. ### About this role: As our Implementation Specialist, you will be responsible for managing and executing the end-to-end implementation of Ashby’s solution for many of our new customers. You will work directly with customers in our Strategic (predominantly Enterprise) segment, developing and executing implementation plans to ensure a positive customer experience and expedited time to value. Your goal is to support our customers, helping them get up and running swiftly with Ashby so they can achieve their desired outcomes. Role requirements: * Implementation & Project Management: You have extensive experience managing and executing several complex implementation and onboarding projects concurrently in a high-growth B2B SaaS org (defining the work, aligning with stakeholders, communicating the project plan, and ultimately delivering results in accordance with the agreed-upon expectations). You keep the team on track to ensure milestones are met. You work effectively in a remote-first setting, with the ability to travel <10% as needed for strategic customer engagements. * Technical Proficiency: You have a strong understanding of complex, configurable B2B SaaS products and their technical intricacies. By “complex”, we mean platforms with multi-step workflows, supporting several core workflows, and integrations with other systems. You’re technically curious and creative. Ashby or ATS experience is a plus, not required. * Customer Centricity: You deeply understand customer needs and tailor implementations to meet their specific requirements. You build strong customer relationships by maintaining high levels of engagement and communication; you’re the customer’s proactive guide and advocate throughout the implementation period. * Change Management: You are experienced in navigating change management processes and helping customers adapt to new systems and a refreshed approach. * Best Practices & Recommendations: You take pride in advising customers on best practices specific to their usage of software to ensure optimal value. * Critical Thinking & Solutions Orientation: You proactively address thematic customer opportunities and improve our processes accordingly. You don’t rely on ‘I’ve seen this done,’ but instead think critically to solve problems. * Cross-functional Collaboration: You effectively partner with cross-functional stakeholders across Customer Success, Sales, Product, Engineering, and Operations to align and define progress. You could be a great fit if: * 📣 You demonstrate clear communication. You ask clarifying questions with precision and can distill complex concepts into simple themes. * 🎧 You are a great listener. You see your role as the voice of the customer to internal stakeholders so we can ensure that our offerings continue to evolve in accordance with customer needs. * 📈 You are a problem solver. You thrive at solving complex challenges with innovative, scalable solutions. * ⚡️You know process matters. You are eager to improve processes and workflows to enhance efficiency and efficacy. * 🔍 Your peers describe you as detail-oriented and technically proficient. You take pride in internal operations. * 📊 You are data-driven. You use metrics and analytics to inform decisions and measure success. * 🌍 You are adaptable. You can navigate changes in a fast-paced, evolving environment. * 🧑‍🏫 You love to coach. You see every teaching moment as an opportunity and are excited to help our customers grow. You might not be a great fit if: * You prefer an in-person role over remote. * You are less interested in customer-facing roles that require both technical and interpersonal skills. * You are accustomed to defining ideas and strategies, yet not responsible for their execution. * You prefer working with a simple product (such as a point solution). * You prefer exclusively to build (rather than build, iterate, optimize). ### Our Philosophy Here are a few key points (relevant to the go-to-market side) that should give you an idea of what it is like to work with us: * We spend a lot of time building best-in-class products since we believe a highly differentiated product is a lot easier to sell. * We want to offer deep expertise whenever we interact with prospects and customers. * We strongly believe that small teams with very talented people (and the right work environment) deliver much better performance than teams with large headcount. We hire and compensate accordingly. * We value a strong sense of ownership, principled thinking over experience, and thoughtful communication (we put a lot of effort into using the right communication channels) – we’ll get into these and other values during the hiring process. ### The Interview At Ashby, our team and interview process want to help you show your best self. Our interview process is structured to get to know you and your career as well as empower you with insight into our key focus areas. Here is the process in its entirety: * 30 min – Recruiter Screen with Talent Team * 45 min – Interview with Hiring Manager * 60 min- Mock Call with 2 Implementation Specialists * Final Round: 30 min – Customer Adoption with Head of Dedicated CS & one of our Strategic CSMs * 30 min – Interview with VP of Customer Success & Head of PS * 10 min – Closing Questions with Hiring Manager ### Benefits * You’ll get the time to do things the right way; we put a lot of emphasis on high quality work and avoid quick hacks as much as possible. * You get to sell a product that our prospects & customers are truly excited about. * Competitive compensation is offered. * 10-year exercise window for stock options. You shouldn’t feel pressure to purchase stock options if you leave Ashby —do it when you feel financially comfortable. * Unlimited PTO with four weeks is recommended per year. Expect “Vacation?” in our one-on-one agenda until you start taking it 😅 * Twelve weeks of fully paid family leave in the US. We plan to expand this to employees in other countries as situations arise. * Generous equipment, software, and office furniture budget. Get what you need to be happy and productive! * $100/month education budget with more expensive items (like conferences) covered with manager approval Ashby provides equal employment opportunities (EEO) to all employees and applicants for employment without regard to race, color, religion, sex, national origin, age, disability, genetics, sexual orientation, gender identity, or gender expression. We are committed to a diverse and inclusive workforce and welcome people from all backgrounds, experiences, perspectives, and abilities. Ashby is committed to a fair and transparent hiring process. We confirm that this advertisement is for an active, existing vacancy within our organization. Please be advised that we may use artificial intelligence-driven tools to assist our recruitment team in screening, assessing, and selecting candidates for this position. 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