Hi, I’m John and I’m the Head of Professional Services at Ashby. One of my favorite aspects of Ashby is our operating principle of Continuous Improvement. Coupled with our principle of caring deeply about our customers, we often find ourselves wondering ‘what is a better way to accomplish this’. That’s why I am thrilled to be hiring our first Enterprise Engagement Manager! As a highly cross-functional member on our growing Professional Services team (within Ashby’s Customer Success organization), you’ll have the opportunity to start shaping our customers’ journeys before they kick off, ultimately upleveling the overall customer experience.
About the Role
As an Engagement Manager, you will have responsibility for implementation and services scoping and design, as well as Statement of Work creation to capture recommendations. The SA is a member of the Professional Services (PS) organization and a close partner to the Enterprise Sales team. Broadly, the goal of this role is to ensure the success of Enterprise customers through professional services.
You will work directly with prospective customers and our Solutions Engineering team during the sales cycle to understand the current state, define a clear path to success, and shape both the deal and implementation approach accordingly. You will provide continuity between what was sold and what is delivered by ensuring a comprehensive handoff from Sales to PS.
This is a high-impact, highly cross-functional role focused on aligning pre-sales motions with implementation work to improve Enterprise sales win rates, accelerate time-to-value, and drive long-term customer outcomes. You will play a critical role in matching prospective customers with the approaches that best meet their needs, while helping Sales win complex deals by increasing buyer confidence and reducing perceived implementation risk.
What You’ll Do
Design and Close Successful Professional Services Opportunities (Pre-Sales)
Act as a trusted advisor to help prospective customers understand how to successfully implement Ashby
Partner with Account Executives and Solutions Engineers to scope and design implementation approaches for complex enterprise opportunities
Translate prospective customer needs and constraints into a tailored path to go-live, including an implementation strategy, success milestones, and services offerings required to support the customer
Align customer stakeholders (including executives) on desired outcomes, timelines, and responsibilities
Create, negotiate, and execute Statements of Work (SOWs) aligned with Professional Services best practices and offerings that accurately the required scope, effort, and sequencing
Create Continuity into Delivery (Post-Sales / Early Lifecycle)
Participate in the Sales handoff to ensure effective transition of recommendations and expectations to the post-sales team
Ensure alignment between pre-sales commitments and post-sales execution by participating in kickoff calls for customers with complex or highly custom recommended approaches
Improve Professional Services GTM Motions
Identify patterns across opportunities (what works, what breaks) and use these to refine our Enterprise Sales motion in partnership with Leadership.
Refine how and when services are introduced and scoped within the sales cycle
Contribute to playbooks, frameworks, and assets that improve how we sell and deliver services
What We’re Looking For
5+ years of experience in Enterprise SaaS across one or more of: Solutions Consulting, Professional Services, or Management Consulting
Strong ability to diagnose business processes and translate them into scalable technical solutions
Experience with complex, multi-stakeholder deals with meaningful implementation components
Comfort navigating collaboration with both pre-sales and post-sales teams
Excellent communication skills, with the ability to influence executives and align cross-functional teams
Strong judgment and ability to balance customer needs, business outcomes, and operational feasibility
What Success Looks Like
Increasing win rates, especially in the Enterprise
Clear alignment between scope, expectations, and customer outcomes
Reduced implementation friction and faster time-to-value
Improved customer confidence and sentiment at kickoff and early lifecycle
Stronger partnership between Sales, Professional Services, and Customer Success
Increased retention and expansion driven by successful customer outcomes
Why This Role Matters
As we move upmarket, the complexity of our customers—and the importance of getting implementations just right—continues to increase. This role ensures we are not just closing quickly, but closing them in a way that sets customers up for long-term success.
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 Head of Professional Services (Hiring Manager)
45 min - Change Management Challenge
Final Round Part 1:
30 min - Interview with VP of Customer Success
30 min - Interview with our Global Head of Solutions Engineering
Final Round Part 2:
30 min - Interview with CEO
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 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.