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# Lessons from Adrian McDermott
- URL: https://www.antoinebuteau.com/lessons-from-adrian-mcdermott/
- Published: 2026-07-01T21:13:27.000Z
- Updated: 2026-08-08T14:42:24.000Z
- Description: Adrian McDermott has guided Zendesk’s technology since its early days, helping scale it into a global platform. His philosophy reframes customer service from a cost center into a source of brand loyalty, with human-centered AI supporting engineering and automation.
- Author: Antoine Buteau
- Tags: Profile, Product Management Profiles

Adrian McDermott is CTO at Zendesk, where he has led product, engineering, and operations through the company’s growth from startup to global customer-service platform. Since June 2025, he has also served as an independent director on Weave’s board. He argues that customer service should move from a cost center to a driver of loyalty, with human-centered AI improving resolution without breaking continuity across the customer journey.

![Visual summary of operating lessons from Adrian McDermott.](https://www.antoinebuteau.com/content/images/2026/07/lessons-from-adrian-mcdermott-profile-infographic.webp)

### Part 1: The Evolution of Customer Experience

1. **On the old model:** "Historically, businesses treated support as a cost center, where success was measured by how fast you could get the customer off the phone." — [*Source: Modern CTO Podcast*](https://moderncto.io/adrian-mcdermott/?ref=antoinebuteau.com)
2. **On brand loyalty:** "The interactions you have when things go wrong define your relationship with a brand far more than the initial purchase." — [*Source: Verdict Interview*](https://www.verdict.co.uk/adrian-mcdermott-zendesk-cto-interview/?ref=antoinebuteau.com)
3. **On friction:** "Customers don't want to explain their problem to three different people. They expect context to travel with them." — [*Source: Speechless Podcast*](https://www.usan.com/podcast/adrian-mcdermott/?ref=antoinebuteau.com)
4. **On metrics:** "Average handling time is a dangerous metric if it incentivizes agents to prematurely close tickets without actually solving the underlying issue." — [*Source: First Round Review*](https://firstround.com/review/how-to-scale-product-and-engineering-a-look-inside-zendesk/?ref=antoinebuteau.com)
5. **On empathy:** "Technology cannot replace empathy, but it can remove the administrative burden so humans have the time to actually be empathetic." — [*Source: Zendesk Blog*](https://www.zendesk.com/blog/adrian-mcdermott-ai/?ref=antoinebuteau.com)
6. **On proactive support:** "The best customer service happens before the customer even realizes they have a problem." — [*Source: Modern CTO Podcast*](https://moderncto.io/adrian-mcdermott/?ref=antoinebuteau.com)
7. **On self-service:** "A knowledge base is only as good as its search function. If users can't find the answer in ten seconds, they will open a ticket." — [*Source: Verdict Interview*](https://www.verdict.co.uk/adrian-mcdermott-zendesk-cto-interview/?ref=antoinebuteau.com)
8. **On omni-channel:** "Being on every channel isn't the goal. The goal is being on the channels your specific demographic actually uses to communicate." — [*Source: Speechless Podcast*](https://www.usan.com/podcast/adrian-mcdermott/?ref=antoinebuteau.com)
9. **On agent experience:** "The interface the support agent uses dictates the quality of service they provide. A clunky backend means a frustrated customer." — [*Source: First Round Review*](https://firstround.com/review/how-to-scale-product-and-engineering-a-look-inside-zendesk/?ref=antoinebuteau.com)
10. **On personalization:** "Greeting a returning customer by name is baseline. True personalization is knowing what they bought, why it might be failing, and having a fix ready." — [*Source: Zendesk Blog*](https://www.zendesk.com/blog/adrian-mcdermott-ai/?ref=antoinebuteau.com)
11. **On Whole-journey handoffs:** Measure the whole customer journey, including whether a handoff carries the customer’s history, intent, and previous steps forward; local speed and AI-resolution metrics can hide repetition and broken continuity. — [*Newsweek*](https://www.newsweek.com/ai-changing-work-companies-bring-back-us-12297203?ref=antoinebuteau.com)

### Part 2: The Reality of Artificial Intelligence

1. **On generative models:** "Generative AI is inherently creative, but enterprise customer service requires deterministic, reliable answers." — [*Source: Modern CTO Podcast*](https://moderncto.io/adrian-mcdermott/?ref=antoinebuteau.com)
2. **On AI hallucination:** "In consumer apps, a hallucination is funny. In financial services or healthcare support, it is a liability." — [*Source: Verdict Interview*](https://www.verdict.co.uk/adrian-mcdermott-zendesk-cto-interview/?ref=antoinebuteau.com)
3. **On implementation:** "Don't buy AI for the sake of having AI. Buy it to solve a specific, measurable bottleneck in your routing or resolution process." — [*Source: Speechless Podcast*](https://www.usan.com/podcast/adrian-mcdermott/?ref=antoinebuteau.com)
4. **On trust:** "The adoption of AI in the enterprise moves exactly at the speed of trust. If the business doesn't trust the model, it won't deploy it." — [*Source: First Round Review*](https://firstround.com/review/how-to-scale-product-and-engineering-a-look-inside-zendesk/?ref=antoinebuteau.com)
5. **On agent assist:** "The immediate value of language models is acting as a co-pilot for the human agent, summarizing past interactions in seconds." — [*Source: Zendesk Blog*](https://www.zendesk.com/blog/adrian-mcdermott-ai/?ref=antoinebuteau.com)
6. **On training data:** "An AI model is a reflection of your underlying knowledge base. If your documentation is a mess, your bot will be a mess." — [*Source: Modern CTO Podcast*](https://moderncto.io/adrian-mcdermott/?ref=antoinebuteau.com)
7. **On intent detection:** "Understanding what a customer is actually asking, despite typos and frustration, is where machine learning shines." — [*Source: Verdict Interview*](https://www.verdict.co.uk/adrian-mcdermott-zendesk-cto-interview/?ref=antoinebuteau.com)
8. **On cost reduction:** "AI will lower the cost of simple transactions to near zero, shifting the budget toward highly trained specialists handling complex edge cases." — [*Source: Speechless Podcast*](https://www.usan.com/podcast/adrian-mcdermott/?ref=antoinebuteau.com)
9. **On transparency:** "When a customer is talking to a bot, they should know it immediately. Deception destroys brand trust." — [*Source: Zendesk Blog*](https://www.zendesk.com/blog/adrian-mcdermott-ai/?ref=antoinebuteau.com)
10. **On fine-tuning:** "General models are good, but fine-tuning a model on your company's specific historical ticket data is what drives actual resolution rates." — [*Source: First Round Review*](https://firstround.com/review/how-to-scale-product-and-engineering-a-look-inside-zendesk/?ref=antoinebuteau.com)

### Part 3: Scaling Product and Engineering

1. **On hiring engineers:** "When you interview a thousand engineers, you start to look for curiosity rather than raw coding speed." — [*Source: First Round Review*](https://firstround.com/review/how-to-scale-product-and-engineering-a-look-inside-zendesk/?ref=antoinebuteau.com)
2. **On technical debt:** "You have to accept a certain amount of technical debt to find product-market fit, but you must pay it down before trying to scale globally." — [*Source: Modern CTO Podcast*](https://moderncto.io/adrian-mcdermott/?ref=antoinebuteau.com)
3. **On monoliths vs. microservices:** "Everyone wants to start with microservices, but a well-structured monolith is often the right choice until your team size forces a split." — [*Source: Verdict Interview*](https://www.verdict.co.uk/adrian-mcdermott-zendesk-cto-interview/?ref=antoinebuteau.com)
4. **On engineering managers:** "The transition from writing code to managing people who write code is a complete career change, not a promotion." — [*Source: First Round Review*](https://firstround.com/review/how-to-scale-product-and-engineering-a-look-inside-zendesk/?ref=antoinebuteau.com)
5. **On global teams:** "Distributed engineering only works if communication is asynchronous by default and documentation is treated as a first-class citizen." — [*Source: Speechless Podcast*](https://www.usan.com/podcast/adrian-mcdermott/?ref=antoinebuteau.com)
6. **On deployment:** "If deploying to production is a high-stress event that requires a weekend, your tooling is fundamentally broken." — [*Source: Modern CTO Podcast*](https://moderncto.io/adrian-mcdermott/?ref=antoinebuteau.com)
7. **On product-led growth:** "The software should explain itself. If a user needs to read a manual to start a trial, the design has failed." — [*Source: Verdict Interview*](https://www.verdict.co.uk/adrian-mcdermott-zendesk-cto-interview/?ref=antoinebuteau.com)
8. **On system reliability:** "Uptime is not a feature; it is the absolute baseline expectation. Nobody praises you for the lights staying on." — [*Source: First Round Review*](https://firstround.com/review/how-to-scale-product-and-engineering-a-look-inside-zendesk/?ref=antoinebuteau.com)
9. **On feature bloat:** "Saying no to a customer request is painful, but adding a feature that only a tiny fraction of users need will eventually suffocate the product." — [*Source: Zendesk Blog*](https://www.zendesk.com/blog/adrian-mcdermott-ai/?ref=antoinebuteau.com)
10. **On refactoring:** "Never stop product development entirely for a rewrite. You have to rebuild the engine while the plane is still flying." — [*Source: Modern CTO Podcast*](https://moderncto.io/adrian-mcdermott/?ref=antoinebuteau.com)

### Part 4: Leadership and Culture

1. **On evangelism:** "A modern CTO cannot sit in a dark room designing architecture. You have to be out talking to customers and explaining the vision." — [*Source: Verdict Interview*](https://www.verdict.co.uk/adrian-mcdermott-zendesk-cto-interview/?ref=antoinebuteau.com)
2. **On failure:** "Blameless post-mortems only work if the leadership team actually models vulnerability when they make their own mistakes." — [*Source: First Round Review*](https://firstround.com/review/how-to-scale-product-and-engineering-a-look-inside-zendesk/?ref=antoinebuteau.com)
3. **On company values:** "Culture isn't what you write on the wall. It is the behavior you tolerate when things are highly stressful." — [*Source: Modern CTO Podcast*](https://moderncto.io/adrian-mcdermott/?ref=antoinebuteau.com)
4. **On retention:** "Engineers leave when they stop learning. If you keep giving them hard problems to solve, they will stay." — [*Source: Speechless Podcast*](https://www.usan.com/podcast/adrian-mcdermott/?ref=antoinebuteau.com)
5. **On alignment:** "Product and engineering must report to the same North Star metric. If product is measured by features and engineering by stability, they will fight." — [*Source: Verdict Interview*](https://www.verdict.co.uk/adrian-mcdermott-zendesk-cto-interview/?ref=antoinebuteau.com)
6. **On impostor syndrome:** "Every leader operating at scale feels like they are making it up as they go. The trick is building a team that catches the things you miss." — [*Source: First Round Review*](https://firstround.com/review/how-to-scale-product-and-engineering-a-look-inside-zendesk/?ref=antoinebuteau.com)
7. **On diversity:** "Building software for a global audience requires a team that actually reflects that global audience's perspectives." — [*Source: Zendesk Blog*](https://www.zendesk.com/blog/adrian-mcdermott-ai/?ref=antoinebuteau.com)
8. **On giving feedback:** "Direct feedback is a form of respect. Withholding criticism because it feels uncomfortable is a disservice to your team." — [*Source: Modern CTO Podcast*](https://moderncto.io/adrian-mcdermott/?ref=antoinebuteau.com)
9. **On remote work:** "The watercooler moments are gone, so you have to engineer serendipity through intentional, unstructured time in meetings." — [*Source: Speechless Podcast*](https://www.usan.com/podcast/adrian-mcdermott/?ref=antoinebuteau.com)

### Part 5: Automation and Service Debt

1. **On service debt:** "When you implement cheap automation that traps customers in endless loops, you accumulate service debt that eventually destroys loyalty." — [*Source: Speechless Podcast*](https://www.usan.com/podcast/adrian-mcdermott/?ref=antoinebuteau.com)
2. **On bad bots:** "A chatbot that acts like a glorified FAQ menu and refuses to hand over to a human is worse than having no bot at all." — [*Source: Modern CTO Podcast*](https://moderncto.io/adrian-mcdermott/?ref=antoinebuteau.com)
3. **On human handoffs:** "The transition from bot to human must be seamless. The agent needs to see the entire chat transcript immediately." — [*Source: Verdict Interview*](https://www.verdict.co.uk/adrian-mcdermott-zendesk-cto-interview/?ref=antoinebuteau.com)
4. **On automation limits:** "Automate the repetitive password resets and order status checks. Leave the complex negotiations and apologies to humans." — [*Source: First Round Review*](https://firstround.com/review/how-to-scale-product-and-engineering-a-look-inside-zendesk/?ref=antoinebuteau.com)
5. **On customer intent:** "Automation fails when it forces the user down a rigid decision tree instead of dynamically responding to their actual intent." — [*Source: Zendesk Blog*](https://www.zendesk.com/blog/adrian-mcdermott-ai/?ref=antoinebuteau.com)
6. **On proactive triggers:** "If the system detects an error on a user's screen, automation should proactively offer a solution before the user even complains." — [*Source: Modern CTO Podcast*](https://moderncto.io/adrian-mcdermott/?ref=antoinebuteau.com)
7. **On measuring success:** "Don't measure automation by how many tickets it deflected. Measure it by whether the customer's issue was actually resolved on the first try." — [*Source: Speechless Podcast*](https://www.usan.com/podcast/adrian-mcdermott/?ref=antoinebuteau.com)
8. **On continuous improvement:** "An automated workflow is never finished. You have to monitor where users drop off and constantly adjust the logic." — [*Source: Verdict Interview*](https://www.verdict.co.uk/adrian-mcdermott-zendesk-cto-interview/?ref=antoinebuteau.com)
9. **On IVR systems:** "Pressing numbers for support is an outdated model. Modern routing should know who is calling and predict why based on recent activity." — [*Source: First Round Review*](https://firstround.com/review/how-to-scale-product-and-engineering-a-look-inside-zendesk/?ref=antoinebuteau.com)
10. **On The automation paradox:** Expect successful self-service automation to expand demand rather than eliminate work: when support becomes easier, customers ask more questions, so efficiency gains can increase total contact volume. — [*CX Foundation*](https://cxfoundation.com/news/ai-drives-contact-volumes-up-not-down?ref=antoinebuteau.com)

### Part 6: Building vs. Buying Software

1. **On core competencies:** "Only build software that is a unique differentiator for your business. Buy absolutely everything else." — [*Source: Modern CTO Podcast*](https://moderncto.io/adrian-mcdermott/?ref=antoinebuteau.com)
2. **On open source:** "Using open source accelerates development, but you have to understand the maintenance burden you are taking on." — [*Source: First Round Review*](https://firstround.com/review/how-to-scale-product-and-engineering-a-look-inside-zendesk/?ref=antoinebuteau.com)
3. **On platform ecosystems:** "A successful enterprise product eventually becomes a platform. You cannot build every integration yourself; you need an ecosystem." — [*Source: Verdict Interview*](https://www.verdict.co.uk/adrian-mcdermott-zendesk-cto-interview/?ref=antoinebuteau.com)
4. **On evaluating vendors:** "When buying software, evaluate the vendor's API first. If the API is an afterthought, the product will be a nightmare to integrate." — [*Source: Speechless Podcast*](https://www.usan.com/podcast/adrian-mcdermott/?ref=antoinebuteau.com)
5. **On vendor lock-in:** "Lock-in is inevitable at scale. The question is whether the vendor provides enough ongoing value to justify the switching costs." — [*Source: Zendesk Blog*](https://www.zendesk.com/blog/adrian-mcdermott-ai/?ref=antoinebuteau.com)
6. **On internal tools:** "Engineers love building internal tools, but those tools often become unmaintained orphans when the creator leaves the company." — [*Source: Modern CTO Podcast*](https://moderncto.io/adrian-mcdermott/?ref=antoinebuteau.com)
7. **On cloud infrastructure:** "The public cloud won the infrastructure war. Spending engineering cycles managing physical servers is a waste of capital." — [*Source: First Round Review*](https://firstround.com/review/how-to-scale-product-and-engineering-a-look-inside-zendesk/?ref=antoinebuteau.com)
8. **On security:** "You can outsource your infrastructure, but you cannot outsource your responsibility for customer data security." — [*Source: Verdict Interview*](https://www.verdict.co.uk/adrian-mcdermott-zendesk-cto-interview/?ref=antoinebuteau.com)
9. **On API design:** "Treat your public API with the same care as your user interface. For developers, the API is the product." — [*Source: Speechless Podcast*](https://www.usan.com/podcast/adrian-mcdermott/?ref=antoinebuteau.com)

### Part 7: Future of Work and Agentic AI

1. **On autonomous agents:** "We are moving from bots that answer questions to autonomous agents that can actually execute tasks across different systems." — [*Source: Modern CTO Podcast*](https://moderncto.io/adrian-mcdermott/?ref=antoinebuteau.com)
2. **On the agent's role:** "The human support agent of the future will function more like an auditor, reviewing the work of AI agents and handling the exceptions." — [*Source: Zendesk Blog*](https://www.zendesk.com/blog/adrian-mcdermott-ai/?ref=antoinebuteau.com)
3. **On seat-based pricing:** "As AI handles more volume, traditional software pricing based on human headcount will have to shift toward outcome-based models." — [*Source: Verdict Interview*](https://www.verdict.co.uk/adrian-mcdermott-zendesk-cto-interview/?ref=antoinebuteau.com)
4. **On skill shifts:** "The premium skill in customer service will shift from rapid data entry to complex problem-solving and emotional intelligence." — [*Source: Speechless Podcast*](https://www.usan.com/podcast/adrian-mcdermott/?ref=antoinebuteau.com)
5. **On system integration:** "Agentic AI is useless if it cannot write to your database. The future is about giving AI the permissions to safely take action." — [*Source: First Round Review*](https://firstround.com/review/how-to-scale-product-and-engineering-a-look-inside-zendesk/?ref=antoinebuteau.com)
6. **On job displacement:** "Technology consistently alters the nature of work, but historically it creates new categories of jobs to replace the ones it automated." — [*Source: Modern CTO Podcast*](https://moderncto.io/adrian-mcdermott/?ref=antoinebuteau.com)
7. **On continuous learning:** "The half-life of technical skills is shrinking. Engineers must optimize for adaptability rather than mastering a single framework." — [*Source: Verdict Interview*](https://www.verdict.co.uk/adrian-mcdermott-zendesk-cto-interview/?ref=antoinebuteau.com)
8. **On collaboration:** "Humans and AI will work in a loop. The AI proposes a solution, the human approves it, and the AI learns from the approval." — [*Source: Zendesk Blog*](https://www.zendesk.com/blog/adrian-mcdermott-ai/?ref=antoinebuteau.com)
9. **On AI governance:** "Allowing autonomous agents to update customer records requires entirely new frameworks for auditing and compliance." — [*Source: Speechless Podcast*](https://www.usan.com/podcast/adrian-mcdermott/?ref=antoinebuteau.com)

### Part 8: The Role of the Modern CTO

1. **On technical vision:** "The CTO's job is not to pick the database. It is to ensure the technical architecture directly supports the business strategy." — [*Source: First Round Review*](https://firstround.com/review/how-to-scale-product-and-engineering-a-look-inside-zendesk/?ref=antoinebuteau.com)
2. **On translating tech:** "You must be able to explain complex technical trade-offs to a board of directors using language they actually understand." — [*Source: Modern CTO Podcast*](https://moderncto.io/adrian-mcdermott/?ref=antoinebuteau.com)
3. **On staying close to the code:** "You can't write production code as a CTO, but you have to read enough of it to know if your engineering standards are slipping." — [*Source: Verdict Interview*](https://www.verdict.co.uk/adrian-mcdermott-zendesk-cto-interview/?ref=antoinebuteau.com)
4. **On navigating hype:** "When a new technology like generative AI arrives, the CTO must separate the marketing noise from the actual engineering utility." — [*Source: Speechless Podcast*](https://www.usan.com/podcast/adrian-mcdermott/?ref=antoinebuteau.com)
5. **On organizational design:** "Shipping fast is often a function of org design. If a team has too many dependencies, they will ship slowly regardless of their talent." — [*Source: First Round Review*](https://firstround.com/review/how-to-scale-product-and-engineering-a-look-inside-zendesk/?ref=antoinebuteau.com)
6. **On legacy systems:** "You can't mandate a rewrite without context. You have to convince the business why untangling legacy code will make them money in the long run." — [*Source: Zendesk Blog*](https://www.zendesk.com/blog/adrian-mcdermott-ai/?ref=antoinebuteau.com)
7. **On cross-functional alignment:** "If the CTO and the Chief Revenue Officer are not talking every week, the company is likely building things that won't sell." — [*Source: Modern CTO Podcast*](https://moderncto.io/adrian-mcdermott/?ref=antoinebuteau.com)
8. **On the CTO lifecycle:** "The skills required to be the CTO of a fifty-person startup are entirely different from those needed at a ten-thousand-person public company." — [*Source: First Round Review*](https://firstround.com/review/how-to-scale-product-and-engineering-a-look-inside-zendesk/?ref=antoinebuteau.com)
9. **On intellectual honesty:** "The most important trait for a technology leader is the willingness to admit when an architectural bet turned out to be completely wrong." — [*Source: Verdict Interview*](https://www.verdict.co.uk/adrian-mcdermott-zendesk-cto-interview/?ref=antoinebuteau.com)