Ashby | $200,000 - $250,000
Steph's Notes:
Brace yourself for an in-depth analysis of Ashby's Careers and Culture materials; I wouldn't normally do this, but considering it's hiring software, it feels appropriate.
There's an odd, rant-like bit on Ashby's careers page about how software products are built. It's not that I disagree with it; it's more that it feels off-topic for a Careers page and thus makes the Careers page seem amateurish and haphazard, which is not a great sign considering Ashby is largely hiring software. It's just weird for a company that should know what it's doing with a Careers page.
Ashby's Culture page is very informative, but it's laid out like a blog, so the posts include dates. This is mostly fine, but it does give the impression that the Culture page hasn't been updated in a while. Again, this is just a polish thing, but given that Ashby is hiring software, it comes across as odd.
Another polish thing that makes me pause: There's a note at the top of Ashby's Operating Principles stating that they consider it to be a "v1 document." But this was published in February 2023, so why is a 3-year-old document still on version 1?
You should always review any materials a company gives you, and it's always a green flag when companies include extra material about their culture, how they operate, etc. I think you should make up your own mind about Ashby's Operating Principles, but FWIW, I think these are really just Values in different clothing, and I find their explanations of the principles muddled in places.
It also feels like Ashby positions its culture and principles in opposition to what other software companies are doing, rather than letting its practices stand on their own merits. To me, this is a minor flag I'd keep an eye on during interviews.
Also, a lot of Ashby's materials are written by its CEO and co-founder, so he's obviously pretty opinionated. This is not necessarily a bad thing! It could mean that he has a good bead on what he wants his company to be, or that the leadership culture is prone to micromanaging. It could mean both. This is where asking specific questions about culture and taking note of who you have access to during the interview process is paramount.
Looking at Ashby's leadership team, it unfortunately hits these BJB squares: *All the women on the leadership team are from Support, Marketing, or Admin*, and *all the women on the leadership team are white.* Aside from that, though, the company seems to be very diverse across teams, so that's a plus.
Finally, here's a big green flag: Ashby lists pay for all positions on the Jobs page (so you don't have to click into the listing to see it), and it does this even for non-US roles. That is a HUGE plus in Ashby's favor, in my opinion.
Okay, on to the job description!
Hi I’m Kelsey 👋 – VP of CS at Ashby. One of my favorite Ashby principles is Implementing Continuous Improvement; it guides how we continually raise the bar on the customer experience. I’m thrilled to be hiring a Head of Global Support to lead our global team and take our world-class support to the next level.
I love that they include this note right at the top of the page.
The "About this role" section is exceptional -- it includes details on the structure of the team this role will lead, how many direct reports they'll have, and a solid overview of what the role will need to accomplish. It's also very complimentary of the existing team. Love it.
The role requirements are thorough and well-articulated. The "You could be a great fit if" section is mostly good, although I'm not the biggest fan of this bullet, because I don't think it's defined properly:
🧠 You are high ceiling. We’re prioritizing high trajectory, principled thinkers over folks who are resting on ‘seen it, done it’.
The "This role may not be a great fit if" section is also excellent and clearly written by someone who understands support well and knows what they're looking for in a candidate.
I love that the interview process is clearly laid out, though it makes me curious about the broader structure of the Support function at Ashby: they mention a VP of CS, a Head of Support, *and* a Head of CS. Again, this isn't a negative; this is just professional curiosity on my part about how they delineate these roles from each other.
The Benefits section is oddly organized, placing "You’ll get the time to do things the right way" at the top of the list and health insurance info at the very bottom, which, again, I just think is a weird polish thing to miss if you're hiring software.
All in all, I think the role itself seems great and is expertly targeted to the candidates they're looking for. However, if I were applying for this role, I'd have questions about broader company culture, so I think Eh, It's Probably Fine is the best fit.
Note: There's a deadline to apply to this role of March 23, 2026 at 10:00 AM MDT. Also, Ashby is hiring for many Support and Success positions worldwide, so be sure to check out their Jobs page!
Original Job Description: Head of Global Support
Hi I’m Kelsey 👋 – VP of CS at Ashby. One of my favorite Ashby principles is Implementing Continuous Improvement; it guides how we continually raise the bar on the customer experience. I’m thrilled to be hiring a Head of Global Support to lead our global team and take our world-class support to the next level.
Our product and growth are exceptional. Ashby’s All-in-One solution is powerful, easy to use, and often replaces 4-5 disparate solutions (ATS, scheduling, analytics, sourcing and CRM). We have several thousand customers, including notable organizations like Shopify and Snowflake. Our growth and retention metrics are best-in-class among our peers: we’re growing >100% year over year, with very low churn and healthy expansion.
About this role:
As our Head of Global Support, you’ll lead an exceptional team of (2) Heads of, (2 soon to be 5) Managers, and (~50) highly technical individual contributors dedicated to delivering remarkable support across every customer segment – from early-stage startups to strategic enterprise organizations. Over the next year, you’ll nearly double this team.
You’ll define how Ashby scales Support as our customer base and product suite grow, partnering closely with Product, Engineering, and Customer Success leadership. Our industry-leading G2 rating reflects our unrelenting high bar: “users rave about Ashby’s top-notch support, noting quick responses and a thoughtful, user-focused approach.”
You’ll build on that foundation: driving continuous improvement, advancing automation, and evolving our 24/7 support model.
Role requirements:
- Customer-Centric Platform Experience: You lead an exceptional global support function for a complex suite of B2B SaaS products, delivering a measurable best-in-class experience.
- Leadership: You have a proven track record of successfully leading and scaling high-performing SaaS Customer Support Teams (we raised our Series D last year and are poised for continued growth).
- Strategic & Operational: You demonstrate a strong command of support operations, including SLAs, schedule optimization, and queue management. You’re experienced in designing efficient support models (ideally including 24/7 coverage, escalation workflows, and specialization). You know how to move resolution up-funnel.
- Cross-functional Partnership: You collaborate effectively with cross-functional stakeholders across Customer Success, Sales, Product, Engineering, and Operations to align support insights with roadmap and customer outcomes.
- Data-Driven, Innovative, and Operational: You leverage data and technology to improve efficiency and quality; comfortable using metrics (CSAT, response times, self-service rates) to inform decisions. You view metrics as a window into the customer experience, not just operational goals, and translate insights into actions that elevate their experience. You proactively address thematic customer issues and improve Support processes to enhance both the efficiency and efficacy of the Support Team.
- Training and Development: You are excited to further our training programs with the goal of empowering our team with the skills and knowledge required to excel in the Support function.
You could be a great fit if:
- 🧠 You are high ceiling. We’re prioritizing high trajectory, principled thinkers over folks who are resting on ‘seen it, done it’.
- 📣 You communicate with clarity. You ask precise questions and can distill complex concepts into simple themes.
- 🎧 You are a great listener. You see your role as 1) advocate for the Support Team as well as 2) voice of the customer to internal stakeholders so we can ensure that our product roadmap continues to move our work forward.
- 📈 You are a strategic problem solver. You thrive at solving complex challenges with principled, scalable solutions.
- 🔍 Your peers describe you as detail oriented. You take pride in internal operations.
- ⚡️You are process-oriented – not for bureaucracy’s sake, but because great systems free people to do their best work.
- ⭐ You stay close to the product. You believe that truly exceptional support comes from deep product understanding – and that everyone on the team shares responsibility for knowing, using, and championing the product we build.
This role may not be a great fit if:
- You don’t need to have already run a massive, multi-layered Support organization; but you do need to show a track record of growing scope, complexity, and ownership. This might look like starting with front-line Support and progressively taking on escalations, incident management, cross-functional problem solving, or operational leadership. We’re looking for someone with the judgment and ambition to scale a full-fledged Support organization over time, and to instill a culture of end-to-end accountability for customer outcomes.
- You’re accustomed to supporting a point solution or simple product. Ashby is sufficiently robust (and increasingly so as we become a platform solution); our Support leader must be familiar with supporting complex products.
- You prefer to focus solely on strategic priorities. We expect that even our most senior leaders are able to ‘traverse the elevation’ and be in the particulars as necessary.
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 offer deep expertise whenever we interact with prospects and customers.
- You can learn more here about our philosophy.
We value a strong sense of ownership, principled thinking over experience, and thoughtful communication (we put a lot of effort into using optimal 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 Senior Recruiter
- 45-60 min - Interview with VP of CS (Hiring Manager)
- 45-60 min - Interview with Head of Support
- Final Round:
- 60 min - Practical Exercise with Support Leaders
- 30 min - Interview with Head of 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.
- 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 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.
