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!
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.
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
Please take your time with your application and the application questions. Although we use AI to assist in our review, we never use AI to auto-qualify or disqualify candidates. We lay eyes on each and every application, and speak to a very select number of candidates based on the application as a whole. This is an evergreen opening, so there is no need to rush, and there are no prizes for being first!
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. You can take a look at our Operating Principles to get a sense of what we are looking for in folks on the team.
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 the Manager, of High Touch Implementations
60 min- Mock Call with Strategic Implementation Specialist and High Touch Implementation Specialist
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
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 😅
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.