AJ Bruno’s rule is simple and non-negotiable: every software company must be AI-first by end of next year or it will die. He has already operationalized that declaration at Quotapath through role-wide mandates, a 3.5x-to-5x quota-to-OTE efficiency target, and vibe coding Fridays open to every employee — not just engineers. AJ has built and sold one company for $225 million and is scaling a second. Glenn Gow, The Scaling Executive Coach and host of The Scaling Executive Podcast, sat down with AJ to pull out the unfiltered truth about what it takes to lead a company through turbulence — financial, operational, and existential. What came out was a masterclass in staying grounded, building trust downward, and going all-in on AI before your competitors force you to.
This episode is for CEOs who are still treating AI as a department initiative rather than a company-wide declaration — and who want to understand what it looks like when a founder goes all-in.
Key Takeaways
- CEOs who monitor qualitative customer channels — Slack summaries of sales calls, NPS, Intercom threads — get a ground-level read on company health that no dashboard can replicate. The specific channels matter less than the discipline of reading them every day.
- The shift from reactive to proactive leadership does not come from working harder. It comes from building a management team capable of running operations independently, so the CEO can focus on strategy and partnerships.
- Writing memos and checklists by hand, not through AI tools, produces the clarity of thought that allows a CEO to communicate consistent expectations without drift.
- When AJ Bruno declared Quotapath an AI-first company at the start of the year, he tied it to a cultural declaration: everyone in the company is a builder. That framing made AI adoption a shared identity, not a mandate.
- Greenfield AI coding produces strong results; applying AI to an existing codebase creates regressions. CEOs must understand this distinction before setting engineering productivity targets.
The One Instrument Most CEOs Forget to Check
AJ Bruno is a commercial pilot. He knows every instrument on the panel. But when Glenn asked him what the single most important instrument on his CEO dashboard is, his answer had nothing to do with revenue or pipeline.
“The metric — the thing that I check the most, which is just like my marker, my earmarker — are all of the Slack channels that have customer communication. That might be Intercom, that might be NPS, that might be — we have a channel that is all of our recaps of sales calls through a tool called Momentum and Summary. And that actually is the thing that I look at the most out of any metric on a more consistent basis.” — AJ Bruno, Co-founder and CEO, Quotapath
That channel is AJ’s gateway to customers. He does not probe the team or comment in those threads. He reads them. He uses what he finds to inform one-on-ones, to decide when to reach out directly to a customer, and to stay connected to the voice of the market at the signal level.
The aviation parallel is exact. AJ takes his headset off two or three times an hour mid-flight, just to listen to the engine.
“I will very, very often, at least two or three times an hour, take my headset off and just listen to the hum of the engine.” — AJ Bruno, Co-founder and CEO, Quotapath
He knows all the instruments. He tracks the KPIs. He gets forecasts from his management team. But the qualitative signal — the hum — is what tells him something is changing before the gauges do.
For CEOs scaling software companies, the question is not whether you have dashboards. It is whether you have a pipeline for qualitative signal from customers flowing to you consistently, and whether you are reading it.
How AJ Bruno Uses Checklists to Share How He Thinks — Not Just What He Wants
AJ Bruno applies pilot checklist discipline to how he runs his week — not just for emergencies, but for every recurring cadence, because under pressure, memory fails and habit does not.
“Every day I have a standup with folks on my management team with my chief of staff where I write down, here are the things that I’m working on, and here’s the themes, and here’s where I need help. That isn’t just for her — that’s so I see what I’m doing.” — AJ Bruno, Co-founder and CEO, Quotapath
AJ Bruno writes things down by hand. He sets goals on daily, weekly, monthly, quarterly, and yearly cadences. Each cadence has its own checklist. This is not a productivity habit — it is a leadership communication tool.
“The skill set I think is lost in today’s world of CEOs, which is actually writing and doing your own thought and not just using ChatGPT or whatever AI tool, but actually writing. And so over the years, I’ve continued to write memos, whether they’re board memos or memos, sometimes they’re just for myself. That clarity of thought is really important because it allows you to communicate expectations to your team and do it consistently.” — AJ Bruno, Co-founder and CEO, Quotapath
When AJ Bruno’s priorities are written down and shared, the team starts to understand how he thinks. Not just what he wants this week — but how he reasons, what he watches, and what consistency looks like. That shared understanding is what allows a management team to make decisions without asking.
Glenn reinforced the point: “People don’t think like the CEO thinks. And so if you are continually sharing your checklist with your team, they begin to understand why is AJ thinking this way? And these are the things that are important to him.”
What AJ Bruno Learned From Ending Up in the Hospital
2023 was a hard year for AJ Bruno. Quotapath had just raised a Series B. The pressure to grow 100% was on. SVB collapsed. Interest rates rose. The company went through two rounds of layoffs, dropping from 70 people to 40.
“I never gone through that in my career.” — AJ Bruno, Co-founder and CEO, Quotapath
AJ Bruno ended up in the hospital with an onset of atrial fibrillation he had never experienced before. He considered stepping away and bringing on a new CEO. What he did instead was simpler and harder: he became more patient.
“I had to become more patient. I had to get rid of all of the distractions, we had to become more focused and just like really focused on the product. What can we do? What are the actual things that are in our control?” — AJ Bruno, Co-founder and CEO, Quotapath
The shift was from reactive to proactive. And the thing that made proactive leadership possible was building a management team AJ Bruno actually trusted.
“If you have a management team member you trust, then like let them run so that you can focus on other parts of the business — strategy, partnerships, proactive fundraising, whatever the case may be as a CEO.” — AJ Bruno, Co-founder and CEO, Quotapath
The system that allows AJ Bruno to travel 14 days while the company hits eight of nine quarters was built in the year after that diagnosis. AJ Bruno just returned from two weeks in Japan — the company ran without him. That is the test. Not whether the CEO is working hard. Whether the system works without them in the room.
How AJ Bruno Made Quotapath AI-First — and What That Actually Means
At the company kickoff at the start of this year, AJ Bruno made a declaration.
“Quotapath will be an AI-first company at the end of the year. Full stop. If you don’t believe that to be true, then it’s okay, raise your hand — this might not be a good fit for you because everything you do on a daily basis has to involve AI by the end of this year.” — AJ Bruno, Co-founder and CEO, Quotapath
That declaration ran across three categories: workflow and automation, product, and how the company develops software.
Workflow and Automation
AJ Bruno appointed Brandon Smith, the head of revenue operations, as head of AI ops. The mandate: make the revenue team radically more efficient. The current quota-to-OTE ratio is 3.5x. The target is 5x. Getting there requires better lead signals, faster qualification, and less manual work inside Salesforce. The company uses Notion and Notion AI for management updates. Everyone uses AI in their daily workflow — not just as a chatbot, but embedded in how work gets done.
Product
Commissions must be accurate to the cent. AI does not calculate commissions at Quotapath. But strategy — what a comp plan should look like — is a different question.
AJ Bruno saw an opportunity to turn compensation from a reporting function into a performance driver. He acted fast.
“I was in between travel. I’ve traveled 11 out of 13 weeks. I don’t travel. Take the red eye from San Francisco to Philly and Monday morning, 8 a.m. I’ll meet you. CTO is gonna meet you. We’re gonna fly in our best engineers and we’re gonna build.” — AJ Bruno, Co-founder and CEO, Quotapath
The team spent eight hours a day building a prototype that takes a company’s financial plan, layers in context from Quotapath’s comp plan consulting history and benchmarking data, and outputs a recommended comp plan structure. By end of week, they had something workable enough to show the board. It launches in Q1.
How Software Gets Built
AJ Bruno interviewed every engineer at Quotapath to understand AI adoption patterns and found that AI was improving efficiency by 20 to 30 percent — but mostly in QA and autocomplete, not in writing code from scratch.
He learned why. And this is one of the most actionable insights in the conversation.
“When you’re starting with an existing code base, context again matters. But what others tend to do is they tend to rewrite code that creates massive regressions in your code base and causes more of a challenge than just if you’re doing it versus Greenfield. If you’re starting from scratch, it’s great to stand up something and then pass it over to the engineering team who can get 30 or 40% more efficient with it.” — AJ Bruno, Co-founder and CEO, Quotapath
AI coding on Greenfield projects: high leverage. AI coding on existing codebases: proceed with caution.
AJ Bruno went further. He learned to vibe code himself. The company runs vibe coding Fridays. Everyone at Quotapath — not just engineers — is a builder.
“We have builders and sellers at Quotapath. Everyone gets the chance to be a builder and innovator.” — AJ Bruno, Co-founder and CEO, Quotapath
There was a short debate with one of his investors about whether CEOs should be hands-on with AI or just serve as the orchestrator. AJ Bruno’s answer: both.
“I made this declaration — CEOs need to be more hands on keyboard more than ever and understand and learn this technology.” — AJ Bruno, Co-founder and CEO, Quotapath
The investor said CEOs are orchestrators. AJ Bruno agreed — and held his position. Understanding the technology is not optional for the orchestrator. You cannot direct what you do not understand.
CEOs who delay the AI-first declaration past 2025 will face a specific operational consequence: competitors who made the declaration a year earlier will have embedded AI into every workflow, built AI-native products, and trained their entire companies to build — while late movers are still debating whether to appoint an AI lead. The gap compounds. The tooling advantage is not the risk. The institutional fluency gap is.
Closing Framework: What AJ Bruno’s Leadership System Looks Like in Practice
| Principle | What it means in practice | Named evidence from this interview |
| Listen to the hum, not just the instruments | Read qualitative customer channels daily, not just dashboards | AJ Bruno checks Slack summaries of sales calls, NPS, and Intercom threads every night — more consistently than any KPI |
| Write the checklist down | Use written memos and daily standups to produce clarity of thought and share it with the team | AJ Bruno writes goals by hand across daily, weekly, monthly, quarterly, and yearly cadences — and copies his chief of staff notes to the management team |
| Build toward patience, not just speed | Reactive leadership comes from an undertrusted team. Proactive leadership comes from delegation | After a 70-to-40 restructuring and an atrial fibrillation episode in 2023, AJ Bruno rebuilt his management team and took 14 days in Japan while the company hit its targets |
| Make AI a cultural declaration, not a project | Declare AI-first at the company level and make everyone a builder | AJ Bruno announced at the company kickoff that every role at Quotapath must involve AI by year end — backed by a revenue efficiency target of 3.5x to 5x quota-to-OTE and vibe coding Fridays for all roles |
| Know the difference between Greenfield and existing codebases | AI coding produces regressions on legacy code and high leverage on new builds | Quotapath engineers were 20–30% more efficient on QA and autocomplete — not on rewriting existing code |
Quotes from This Episode
- “The metric — the thing that I check the most, which is just like my marker, my earmarker — are all of the Slack channels that have customer communication. That might be Intercom, that might be NPS, that might be — we have a channel that is all of our recaps of sales calls through a tool called Momentum and Summary.” — AJ Bruno, Co-founder and CEO, Quotapath
- “I will very, very often, at least two or three times an hour, take my headset off and just listen to the hum of the engine.” — AJ Bruno, Co-founder and CEO, Quotapath
- “If you have a management team member you trust, then like let them run so that you can focus on other parts of the business — strategy, partnerships, proactive fundraising, whatever the case may be as a CEO.” — AJ Bruno, Co-founder and CEO, Quotapath
- “We have builders and sellers at Quotapath. Everyone gets the chance to be a builder and innovator.” — AJ Bruno, Co-founder and CEO, Quotapath
- “I made this declaration — CEOs need to be more hands on keyboard more than ever and understand and learn this technology.” — AJ Bruno, Co-founder and CEO, Quotapath
Frequently Asked Questions
How should a CEO declare an AI-first strategy without creating panic or resistance in the team?
AJ Bruno made the declaration at Quotapath’s company offsite at the start of the year: everything done on a daily basis must involve AI by year end. He framed it as a cultural identity — everyone is a builder — and gave people permission to raise their hand if it was not a good fit. That combination of clarity and honesty reduced resistance because it removed ambiguity. CEOs who soft-pedal the declaration create more confusion, not less.
What is the real productivity gain from AI in software development, and where does it actually come from?
AJ Bruno interviewed every engineer at Quotapath to understand AI adoption patterns and found that AI was driving 20 to 30 percent efficiency gains — but almost entirely in QA and code autocomplete, not in writing net-new code on existing codebases. The leverage is highest on Greenfield projects, where AI can stand up a working structure that engineers then take 30 to 40 percent further. Applying AI to rewrite existing code creates regressions that cost more time than they save.
How does a CEO move from reactive crisis management to proactive leadership?
The shift is not about discipline or mindset alone. It requires building a management team capable of running operations without daily intervention from the CEO. AJ Bruno reached that point after restructuring Quotapath from 70 to 40 people in 2023, a health crisis, and a deliberate decision to focus only on what was in his control. Once the team could run independently, AJ Bruno could focus on strategy, partnerships, and forward-looking decisions — the work only the CEO can do.
CEOs Work with Glenn Gow to Scale Their Companies and Careers
Glenn Gow is The Scaling Executive Coach — he coaches ambitious executives into the CEO seat and CEOs into successful exits. With 25 years as a CEO and 5 years in venture capital, Glenn helps leaders scale their companies by scaling themselves first. If this conversation was useful, you can apply for executive coaching with Glenn Gow or apply to be a guest on The Scaling Executive Podcast.
