All remote jobs

Senior Strategic Implementation Specialist – Americas (EST)

Review the role, location requirements, compensation details, and application process before deciding whether this opportunity fits your next career move.

Remote from
USA, Canada
Salary
USD 165k–185k / yr
Employment
Full Time
Experience
Director
Published
Apply before
7 Nov 2026
Listing views
16
Application actions
1
Application 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 customer-facing implementation professional to lead end-to-end deployments of its B2B SaaS recruiting platform for strategic, predominantly enterprise customers. The role combines implementation project management, technical product configuration, change management, customer advisory work, and cross-functional coordination. The successful candidate will manage multiple complex onboarding programs while driving adoption, milestone completion, and faster customer time to value. This is a remote, full-time role available in the United States and Canada, with an Eastern Time Zone requirement and less than 10% travel. Strong written and verbal communication, independent judgment, process improvement, and data-informed decision-making are central to success.

Role DNA

A quick view of the complexity, pace, ownership and collaboration implied by the job description.

Job Complexity

4/5
EasyHard

Pace & Pressure

4/5
RelaxedFast-paced

Autonomy Level

5/5
GuidedFull ownership

Communication Load

5/5
IndependentCollaborative
AI insightThe role requires concurrent ownership of complex enterprise SaaS implementations, including technical workflows, integrations, stakeholder alignment, and change management. It demands strong independent execution while balancing customer expectations and coordination across Product, Engineering, Sales, Customer Success, and Operations.

Salary analysis

Estimated compensation compared with the broader US market for similar roles.

Estimated job medianHighly competitive
$175,000
US market range$140k–$190k
AI insightThe disclosed annual salary range is $165,000-$185,000 USD, producing a job median of $175,000 USD. This sits competitively within the estimated US market range of $140,000-$190,000 USD for senior enterprise SaaS implementation and professional services specialists; the market range is an estimate, while the job range is explicitly disclosed.

Core skills

Skills and capabilities most closely associated with this opportunity.

Sample interview questions
How would you structure an implementation plan for a new enterprise customer with multiple stakeholders and integrations?

I would begin with discovery to document business goals, success criteria, workflows, technical dependencies, stakeholder roles, and risks. I would turn these findings into a phased plan with named owners, milestones, decision points, a communication cadence, and measurable adoption outcomes, then review the plan jointly with the customer and internal teams.

Describe how you handle a customer whose requirements change midway through implementation.

I first clarify the business reason, urgency, and impact of the requested change. I assess scope, timeline, technical implications, and trade-offs with the relevant internal teams, present options transparently, and document the agreed path so expectations remain aligned.

How do you explain a complex SaaS workflow or integration to a nontechnical customer stakeholder?

I start with the stakeholder's desired business outcome and use plain language to connect the workflow to that outcome. I avoid unnecessary technical detail, use examples or visual process maps where helpful, confirm understanding through questions, and provide practical next steps and supporting documentation.

What metrics would you use to evaluate implementation success?

I would use a combination of delivery and outcome metrics: time to launch, milestone attainment, onboarding completion, configuration and integration readiness, user adoption, training participation, customer satisfaction, and progress toward the customer’s stated business objectives. I would review these metrics throughout the project rather than only at go-live.

Tell us about a process improvement you would introduce after seeing a recurring implementation issue.

I would identify the recurring pattern through project feedback and delivery data, determine its root cause, and propose a scalable intervention such as a revised discovery checklist, configuration template, enablement guide, or escalation workflow. I would pilot the change, measure its effect on delivery quality or time to value, and incorporate it into the standard process if it proves effective.

This analysis is generated from the job description. Salary estimates, role characteristics and sample answers are guidance, not employer-provided facts.
Opportunity details

About this role.

Senior Strategic Implementation Specialist, Americas (EST)

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, specifically in the EST time zone. 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 are not located in the Eastern Time Zone.

  • 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.

Apply now >

This job listing has been manually reviewed by the Jobicy Trust & Safety Team for compliance with our posting guidelines, including verification of the company's legitimacy, accuracy of job details, clarity of remote work policy, and absence of misleading or fraudulent content.

Next step

Apply now.

Follow the employer’s application method and review Jobicy’s safety guidance before sharing personal information.

Did you apply?Let us know, and we’ll help you track your application.

Continue on the employer website

Protect your personal information and never pay to secure an interview or job offer. .

Log in to save
One quick step before you apply

Sign in to continue.

Sign in or create a free account to continue to the employer's application.

Applying is free. After signing in, return to this job and select Apply Now.
Add alert
Jobs Talent AI Tools Salaries
Menu