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Ashby

Mid-Market Implementation Specialist - Americas

Canada

Full-time

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Job details

Job type: Full-time
Posting language: English
Posted: Nov 10, 2026

Original job description

Mid-Market Implementation Specialist

Hi! I'm Daryl, and I'm the Manager of High Touch (Mid-Market) Implementations at Ashby. One of my favorite things about this team is that we're the first real proof point for a new customer; from day 1, we get the hands-on opportunity to show them why they made the right call switching to Ashby.

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 Mid-Market 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 15-20 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 15-20 active mid-market implementations at a time (8-10 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:

5+ 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 concurrent mid-market 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

About Ashby

We’re building the next generation of enterprise software, and we’re starting with a suite of products that help talent leaders, recruiters, and hiring managers run their hiring process significantly better. Learn more on our website: https://www.ashbyhq.com/

We are well funded and backed by great investors, including Y Combinator, Elad Gil and Lachy Groom. We have thousands of amazing customers including Snowflake, OpenAI, Shopify, Ramp, Notion, and Zapier (and many others who we cannot name!). Our growth and retention metrics are best-in-class among our peers: we have tens of millions in ARR, growing >100% year over year, very low churn, and many years of runway. We’ll share more details once we meet. In short, it's the perfect time to join! 🚀

Instructions

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!

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. You can take a look at our Operating Principles to get a sense of what we are looking for in folks on the team.

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.

Compensation Range: $120,000 - $170,000

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More about this job

Responsibilities

Manage 15–20 concurrent mid-market customer implementations from sales handoff through go-live, including project plans, timelines, configuration, troubleshooting, and customer guidance. Partner with Sales, Customer Success, Product, and Engineering, while improving implementation processes and sharing customer feedback.

Requirements

Requires 5+ years in customer-facing roles, primarily leading full-cycle B2B SaaS implementations, with a record of managing concurrent mid-market projects independently. Candidates should be technically resourceful with complex, multi-module software and able to troubleshoot, advise customers, execute project plans, and improve processes.

Skills

B2B SaaS Implementation
Project Management
Technical Troubleshooting
Software Configuration
Workflow Design
Customer Advising
Cross-Functional Collaboration
Product Knowledge
Process Improvement
Customer Feedback
Data-Driven Decision-Making
Attention to Detail
Customer Coaching
Stakeholder Communication

Benefits

Competitive Compensation
Stock Options
Unlimited Paid Time Off
Paid Family Leave
Equipment, Software, and Office Furniture Budget
Education Budget

Visa sponsorship

Not detected in the job text

Hiring contact

Daryl

Keywords

B2B SaaS
Mid-Market Implementations
Customer Onboarding
Go-Live
Project Planning
Project Timelines
Software Configuration
Workflow Design
Technical Troubleshooting
Multi-Module Software
Customer Success
Sales Handoff
Product Feedback
Product and Engineering Collaboration
Cross-Functional Collaboration
Process Improvement
Customer Adoption
Customer Enablement
Implementation Best Practices
Escalation Management
Talent Acquisition Software
Recruiting Software

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Work requirements

Jobs in Canada