Senior Strategic Implementation Specialist - Americas

Ashby; Oregon; Hybrid; USD 120,000 - 170,000; Full time

Benefits offered by this job

Unlimited PTO

Stock options – 10 year exercise

$100/month education budget

Generous equipment budget

Job summary

Ashby, Inc. is seeking a Senior Strategic Implementation Specialist for the Americas. You will own technically complex SaaS implementations from handoff to go-live, managing multiple clients with autonomy.

You’ll troubleshoot deeply, propose optimized configurations, and collaborate with Sales, CS, and Product/Engineering to improve the product and the customer journey. You’ll work within Ashby’s Professional Services team in Customer Success, guiding customers through successful setup and

Qualifications

• 7+ years of experience in a customer-facing role, with the majority of focus on leading full-cycle B2B SaaS implementations.
• Proven track record successfully managing upmarket concurrent implementation projects without compromising quality, customer experience, or timelines.
• Experience operating with real autonomy and owning the implementation project plans end-to-end.
• Comfortable getting into the weeds of complex, multi-module software, and building fluent understanding of how it all fits together.
• Resourceful when there’s no documented answer; you do your own testing and discovery and advise customers on best practices.
• Data-driven and detail-oriented, with a genuine instinct for coaching customers through unfamiliar territory.

Responsibilities

• Manage 8–12 active enterprise implementations at a time with 12–16 week timelines, building each customer’s project plan from handoff through go-live and tracking milestones.
• Develop deep product fluency to troubleshoot and advise beyond simple checklists.
• Advise on configurations and workflows that balance customer needs with implementation best practices.
• Partner closely with across the business—Sales, CS, Product/Engineering—to ensure a seamless customer journey and flag issues.

Job description

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.

The Ashby team has grown rapidly over the last few years, and we're not slowing down: we added more than 2,100 new customers in the last year alone and now support over 5,000 customers, with ARR growing much faster than 100% year over year. We're expecting similarly fast growth this year, and every one of those new customers needs a thoughtful implementation to actually get value out of Ashby. We'll share more details once we meet, but you probably have a good idea as to why we're expanding this team!

The Role:

We're looking for a Senior Strategic Implementation Specialist who excels at leading technically complex, hands on implementation projects for B2B SaaS customers. You'll own each implementation from the moment Sales hands it off through go-live; part project manager, part technical expert, and part trusted advisor to the customer! Six months in, success looks like carrying a full book of 8-12 active implementations, running each customer relationship on your own (kickoff, timeline, follow-through), independently solving complex configuration and workflow challenges, and handling the normal bumps (a slow-to-respond customer, a technical snag, an escalation) without the rest of your book slipping. It also means you're starting to make things better beyond your own accounts: you've found at least one process or documentation gap and fixed it, and you're feeding real customer feedback back to our Product team.

You will achieve this by:

• Managing 8-12 active enterprise implementations at a time (12-16 weeks implementation timeline on average), building each customer's project plan from handoff through go-live, and staying on top of timelines, hurdles, and follow-up along the way
• Getting genuinely comfortable with the in's and out's of how our products work, so you can troubleshoot and advise instead of just walking through a checklist
• Advising on what's worked well for similar customers in the past, challenging assumptions when appropriate, and recommending configurations and workflows that balance customer needs with implementation best practices
• Partnering closely with cross-functional partners across the business, especially Sales and CS to ensure a seamless customer journey, and Product/Engineering to flag real issues and align on a path forward

As you're probably gathering, we're looking for someone who gets energy from both sides of this: the structure of running a tight project plan, and the judgment to rethink that plan when a customer's business genuinely calls for it.

If you have the majority of the following, you could be a great fit for this role:

• 7+ years of experience in a customer-facing role, with the majority of your focus on leading full-cycle B2B SaaS implementations
• Proven track record successfully managing upmarket concurrent implementation projects without compromising quality, customer experience, or timelines
• Experience operating with real autonomy and to own the implementation project plans end-to-end
• Comfortable getting into the weeds of complex, multi-module software, and building genuine fluency in how it all fits together
• Resourceful when there's no documented answer; you do your own testing and discovery, then use what you learn to advise customers on best practices and recommendations
• Data-driven and detail-oriented, with a genuine instinct for coaching customers through unfamiliar territory

If you need someone else to do any of the following, then this role is probably not for you:

• Independently investigate complex customer questions and become the technical/product subject matter expert during implementations
• Carry more than a handful of accounts at once (this is a high volume role on a team that moves with urgency)
• Own the execution of a project plan, not just its design
• Iterate and improve on existing processes

Our Philosophy

• 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.

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 Manager of High Touch Implementations
• 60 min- Mock Call with an Implementation Specialist and Customer Success Manager

Final Round:

• 30 min - Cross-Functional Interview with Head of Professional Services
• 30 min - Product Complexity Interview with VP of Customer Success
• 30 min - Customer Adoption & Enablement with Manager of High Touch Customer Success and a High Touch Customer Success Manager
• 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.