Hi! I'm Allie, Head of Support at Ashby. 👋 I have had the privilege of working with an incredible Support Team full of highly knowledgeable, driven team members who care deeply about the success of our customers.

As Ashby grows, the complexity of our customers’ workflows, integrations, and technical environments continues to increase. We are building a Support Engineering function that can both resolve deeply technical issues and influence how our product evolves to prevent those issues in the first place.

To help us scale this capability, we are hiring a Director of Support Engineering to partner closely with Engineering, shape our long-term supportability strategy, and ensure that technical insights from Support meaningfully influence our product and platform.

This role is focused on systems-level impact and oversight of a Support Engineering Manager, as well as the Support Engineers. You will help design how Support and Engineering work together, identify structural improvements that reduce escalations, and build tooling and enablement that makes our Support organization dramatically more effective.

If you enjoy solving systemic problems, influencing engineering priorities, and designing scalable technical support systems, this role will give you a rare opportunity to shape how a high-growth company operates.

About This Role

As the Director of Support Engineering, you will lead the strategic evolution of Ashby’s Support Engineering function. Operating at the intersection of Support, Engineering, and Product, you will define how technical support operates at scale by shaping the systems, tools, and cross-functional partnerships that enable the team to be highly effective.

You will lead and develop a high-performing Support Engineering organization through strong, engaged management of Support Engineering Managers and their teams. As a leader of leaders, you will set a clear vision for how the function scales, drive alignment across leadership, and create an environment where both managers and individual contributors can do their best work.

You will coach and support Support Engineering Managers in driving team performance, navigating complex technical and organizational challenges, and growing as leaders. This includes establishing clear expectations, providing structured feedback, and fostering accountability at every level of the organization.

You will play a key role in organizational design, ensuring the team structure evolves alongside increasing product complexity and customer needs. This includes identifying gaps in skills or coverage, supporting hiring and onboarding, and building career paths that enable long-term growth within Support Engineering.

In parallel, you will clarify ownership boundaries between Support and Engineering, develop mechanisms to reduce recurring issues, and ensure that insights from Support translate into meaningful product and platform improvements.

Throughout, you will focus on creating clarity, consistency, and leverage—ensuring that priorities, processes, and decision-making frameworks scale effectively while maintaining a strong, customer-centric culture.

Role Responsibilities

Strategic Engineering Partnership

• Partner closely with Engineering leadership to improve how technical issues are surfaced, investigated, and resolved

• Help define clear ownership boundaries between Support and Engineering for bugs, performance issues, and platform limitations

• Drive alignment on escalation pathways, debugging expectations, and response patterns for complex customer issues

• Advocate for supportability and operability as core product design considerations

Escalation & Supportability Strategy

• Analyze patterns in escalations, bugs, and technical customer friction to identify systemic improvements

• Work with Engineering and Product teams to prioritize fixes that reduce recurring support load

• Develop frameworks for how support insights influence engineering roadmap discussions

• Improve the feedback loop between Support, Engineering, and Product

Technical Enablement & Tooling

• Identify gaps in diagnostics, logging, tooling, and workflows that limit Support’s ability to resolve technical issues

• Partner with Engineering teams to design or implement tooling that improves debugging, triage, and issue resolution

• Build scalable internal systems that allow Support to resolve more issues without Engineering involvement

• Raise the technical leverage of the Support organization

Data & Insight Leadership

• Turn support escalation data into actionable insights that influence product and engineering decisions

• Identify patterns in technical friction and propose high-impact improvements

• Develop reporting frameworks that make the support impact of engineering decisions visible

Organizational Design & Support Engineering Strategy

• Partner with the Head of Support to shape the long-term evolution of the Support Engineering function

• Ensure the function scales effectively as Ashby’s product surface area and customer complexity grow

Role Requirements

Engineering Partnership Experience

• Experience collaborating deeply with engineering teams to resolve production issues or improve product supportability

• Track record of partnering with Engineering teams through data, context, and technical insight

• Strong judgment in navigating cross-team priorities and tradeoffs

Strategic Problem Solving

• Ability to identify patterns in complex operational systems and design durable improvements

• Comfort operating in ambiguity and designing structures where none exists

• Strong bias toward pragmatic solutions that deliver real impact quickly

Customer-Centric Technical Leadership

• Passion for improving the customer experience through technical excellence

• Ability to represent customer impact clearly in engineering discussions

• Understanding of how technical decisions affect supportability and long-term scalability

Technical Depth & Systems Thinking

• Strong technical background in software engineering, technical support engineering, infrastructure, or similar fields

• Comfort discussing architecture, debugging approaches, APIs, integrations, and system behavior

• Ability to identify structural issues in technical workflows and design scalable solutions

You Should Apply If

• You enjoy solving systemic problems that span teams and functions

• You want to influence how Engineering and Support collaborate at a growing SaaS company

• You care about making support more technically capable and more strategically impactful

• You are energized by turning operational friction into product improvements

You May Not Want to Apply If

• You prefer roles focused primarily on people management or ticket oversight

• You are uncomfortable influencing engineering strategy or challenging technical decisions

• You prefer operating within established systems rather than designing new ones

Our Interview Process

Our interview process is thorough — we aim to ensure each person that joins the team is the right fit for Ashby and will provide ample information for you to assess if Ashby is the right fit for you. The process for this role is as follows:

• Intro Call with Recruiting - 30 min

• Hiring Manager Interview - 45-60 min

• Take Home Assessment

• VP of Customer Success Interview - 30 min

• Founder Interview - 30 min

• Final Round:

  • Support Strategy & Customer Experience interview - 30 min

  • Engineering Partnership, Influence & Vision - 30 min

If you're excited about leading a highly technical team, eliminating friction, and shaping the future of Support Engineering at Ashby, we’d love to hear from you!

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 – whether it be through scaled engagements (e.g. webinars), 1:1 conversations, or through written word (e.g. documentation).

• 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.

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.

If you're excited about shaping how Support Engineering operates at scale and partnering closely with Engineering to improve the Ashby platform, we'd love to hear from you.

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.