Head of Professional Services

Head of Professional Services

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’m thrilled to be hiring our Head of Professional Services! As a leader on our Customer Success team, you’ll have the opportunity to elevate the customer experience to the next level through operational excellence and programmatic efforts. You’ll join the current leadership team, working alongside our Heads of: Strategic Customer Success, High Touch CS, Startup CS, Support and Contract Management.

About this role:

As the Head of Professional Services, you will play a pivotal role in ensuring our customers continue to have remarkable experiences with Ashby as we scale.

You will shape our Professional Services offerings to support each segment of our customer base (Small Businesses through Enterprise) by refining our current SKUs and creating new ones to meet various customer needs. You’re comfortable partnering in Sales conversations, creating and executing custom statements of work for bespoke offerings. Ultimately – you care deeply about the opportunities before our customers and 1) understand how to package offerings to help them achieve their goals with Ashby while 2) leading (and growing) our team of Recruiting Operation Consultants and Implementation Specialists.

Role requirements:

• Programmatic Experience: You have B2B SaaS experience in which you’ve developed and implemented scalable Professional Services programs (such as training and enablement) to increase customer retention and growth, or otherwise combat churn.

• Implementation Expertise: You have extensive experience managing and executing large scale custom implementation projects (scoping the work, aligning with stakeholders, managing the project plan, navigating change management, and ultimately delivering results in accordance with the defined expectations).

• Strategic Thinking: You are skilled at understanding and improving the customer experience through service offerings. You are keen to build an elevated Professional Services function, ensuring team goals connect to company objectives.

• Innovative & Principled Approach: 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.

• Proven Leadership: You have a track record of successfully growing, leading and developing high-performing teams in a SaaS environment, bolstering a culture of excellence.

You could be a great fit if:

• 🧑‍🏫 You have led a high performing team of Professional Services folks, specifically with an emphasis on implementation and consulting services.

• 🔗Your B2B SaaS Professional Services experiences cover the entire customer lifecycle (kick-off through renewal).

• 🔍 You’re experienced in scoping and defining custom SOWs for Enterprise customers to help them achieve their goals.

• 🛠 You have a track record of strategy coupled with hands-on execution. You've successfully led teams in delivering complex, custom implementations by managing project timelines and resources to ensure high customer satisfaction.

• 📈You have direct experience working at a management consulting firm; we anticipate this as highly transferable experience.

• 📣 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 know process matters. You are eager to improve processes and workflows to enhance efficiency and efficacy.

• 📊 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 might not be a great fit if:

• You prefer an in-person role over remote.

• You’re not eager to roll up your sleeves and get into the weeds (e.g. managing an implementation isn’t interesting to you).

• You are accustomed to defining ideas and strategies, not responsible for their execution.

• You prefer working with a simple product.

• 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 GTM Recruiter

• 45-60 min - Interview with VP of CS (Hiring Manager for role)

• 30 min - Interview with current Implementation Specialist and Rec Ops Consultant (team members)

• Practical Exercise

• Final Round:

  • 45-60 min - Interview with Head of Startup CS & Head of Support

  • 45-60 min - Interview with VP of Sales & Head of Strategic CS

  • 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, with a 401k match in the US

• 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

• If you’re in the US, top-notch health insurance for you and your dependents with all premiums covered by us.

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.