Glenn Gow, The Scaling Executive Coach and host of The Scaling Executive Podcast, talks with Steven Monterroso, CEO of ShareVault, about the signal that tells a CEO it is time to delegate, and what that same discipline means for prioritization, deal readiness, and AI adoption.
This conversation is for CEOs who are still running their day off a to-do list and need to know when that means it’s time to delegate.
When a CEO catches themselves running through a daily to-do list, Steven Monterroso, CEO of ShareVault, treats that as the signal to delegate rather than push harder. He holds his team to an 80 to 90 percent execution standard instead of demanding the perfection that keeps every decision routed through him, which frees him to focus on strategy instead of tasks.
Monterroso spent over 15 years leading sales, marketing, and customer success at fast-growing SaaS companies, including 8×8, Blue Jeans Network, and Biba Systems, before Amazon acquired Biba. He now leads ShareVault, a secure platform built for M&A, fundraising, and other high-stakes transactions, and hosts his own podcast, This Is M&A. That background gives him a direct view into what separates CEOs who scale themselves from CEOs who stay buried in their own operations.
Key Takeaways
- A CEO who spends each day working through a to-do list is showing the clearest sign that delegation, not more effort, is the fix. Monterroso holds his team to an 80 to 90 percent execution standard rather than demanding the perfection that keeps decisions bottlenecked at the top.
- Companies are bought, not sold. Monterroso argues that CEOs who operate with a deal-ready mindset before a buyer appears, keeping their cap table, financials, and customer concentration in order, position themselves to grow and prepare for an exit at the same time instead of trading one for the other.
- When scaling rapidly, Monterroso prioritizes the initiatives with the highest impact and clearest reward first, and deliberately leaves lower-impact problems unresolved rather than splitting focus across everything that surfaces.
- Before deploying AI further, Monterroso audited ShareVault’s internal data and systems to confirm they were feeding clean information into its tools, reasoning that AI layered on top of messy operations multiplies the mess instead of solving it.
- ShareVault built an AI redaction feature that automatically blocks out sensitive information, such as Social Security numbers and driver’s license numbers, in due diligence documents, a task that used to require manual review line by line.
How CEOs Know When to Delegate Instead of Push Harder
Monterroso built his career in revenue roles, where effort and results move together. More calls and more emails produce more sales. Running a company does not work that way. “You can’t outwork bad processes, bad systems.” He names three requirements for scaling a CEO out of the day-to-day: the right people, the right processes, and the right systems. Without them, a CEO stays trapped doing the work instead of building what lets the work get done without them.
The test he uses is simple. If your day is structured around clearing a to-do list, you are operating as an individual contributor, not a CEO. “That’s what you should take as, if I’m working off of a to-do list and every day I’m just coming in trying to get through that to-do list, that’s a problem.” His fix is delegation, and the sticking point most CEOs hit is wanting the work done at 100 percent because it carries their name and reputation. Monterroso sets the bar at 80 to 90 percent instead. That standard lets his team move without waiting on him, and speed matters more than the last 10 percent of polish. “Executing quicker is a lot more important than being bottlenecked by a CEO.”
How CEOs Prioritize Competing Problems While Scaling
Rapid growth surfaces more problems than any CEO can solve at once. Monterroso ranks them by impact and reward before deciding what gets attention now versus what waits. “You have to really think about what’s going to have the biggest impact first, and you have to prioritize based on what’s going to drive the results.”
That ranking only works if the CEO is also willing to say no to good ideas that fall outside it. Since taking over ShareVault, Monterroso made staying in the company’s lane a core operating principle. “We’re going to stay our lane, we know what we do, we’re going to put blinders to all the other stuff.” The discipline is not identifying good opportunities, it is declining the ones that do not serve the current priority, even when they look promising on their own.
How CEOs Build a Deal-Ready Business Without Slowing Growth
Most CEOs treat deal readiness as something to address once a buyer shows interest. Monterroso runs ShareVault the opposite way. “Companies are bought not sold.” The distinction is not a slogan for him. It changes how he manages the cap table, the financial documents, and the operating model on an ongoing basis, so the business is prepared the moment someone comes knocking rather than scrambling to organize itself under deadline pressure.
Operating with a deal-ready mindset also changes how a CEO grows the business, not just how they document it. Monterroso points to customer concentration as an example: a company that leans too heavily on one large customer looks fine day to day, but that concentration becomes a liability the moment a buyer starts asking questions. “We don’t want so much customer concentration.” Thinking like a buyer earlier surfaces those risks while there is still time to correct them, which means deal readiness and growth strategy reinforce each other instead of competing for the CEO’s attention.
How CEOs Prepare Their Data Before Deploying AI
Before ShareVault expanded its use of AI, Monterroso ran an audit of the company’s internal data and systems first. “Your AI is only as good as what you’re feeding it with.” His reasoning: a company with disorganized systems does not fix that disorganization by adding AI on top of it. It multiplies the existing mess instead. He advises CEOs to check whether their metrics and systems are already reliable without AI before layering AI in. If they are not, AI is not ready to help yet.
Once that foundation was in place, ShareVault moved quickly on both internal tools and customer-facing features. Internally, the product team uses AI coding tools to accelerate development, which Monterroso calls a genuine advantage for a bootstrapped company. On the customer side, ShareVault built an AI redaction feature that automatically identifies and blocks sensitive information, such as Social Security numbers and driver’s license numbers, in due diligence documents, work that previously required someone to review each document by hand.
Delegation, Focus, and Clean Data: A Framework for Scaling CEOs
| Principle | What it means in practice | Named evidence |
| The to-do list is the delegation signal | When a CEO’s day is consumed by a running task list instead of strategic decisions, that is the cue to hand off execution rather than work longer hours | Monterroso’s 80 to 90 percent execution standard eliminated CEO sign-off as a step in ShareVault’s team decisions, shifting his time from task review to strategic work such as M&A positioning and AI rollout planning |
| Prioritize for impact, not urgency | Rank competing problems by the size of the result they will produce, and deliberately let lower-impact issues wait rather than splitting attention across all of them | Monterroso’s lane-focused operating principle kept ShareVault’s growth effort on its core M&A and fundraising platform rather than diverted into adjacent product lines, concentrating engineering and go-to-market resources on the initiatives most likely to drive revenue |
| Companies are bought, not sold | Keep the cap table, financials, and operating documents in order continuously so the business is ready the moment a buyer appears, instead of organizing everything under deadline pressure | Running ShareVault with this mindset surfaced customer concentration as a risk before any sale conversation began, giving Monterroso time to diversify the customer base rather than disclose the concentration under deadline pressure to a buyer |
| Clean data before AI | Audit internal systems and data quality before layering AI on top, since AI trained on disorganized inputs multiplies existing problems instead of solving them | ShareVault’s data audit produced an AI redaction tool that now automatically blocks sensitive data such as Social Security and driver’s license numbers in due diligence documents, work that previously required manual, document-by-document review |
Quotes from This Episode
- “Revenue doesn’t solve quite all problems across all departments.” — Steven Monterroso, CEO, ShareVault
- “The one metric that I’m really paying more attention to than ever is EBITDA.” — Steven Monterroso, CEO, ShareVault
- “We don’t want so much customer concentration.” — Steven Monterroso, CEO, ShareVault
- “You can’t outwork bad processes, bad systems.” — Steven Monterroso, CEO, ShareVault
- “Executing quicker is a lot more important than being bottlenecked by a CEO.” — Steven Monterroso, CEO, ShareVault
Frequently Asked Questions
How do I know when it’s time to delegate instead of working harder as a CEO?
Steven Monterroso, CEO of ShareVault, points to a specific signal: if your day is built around clearing a to-do list, you are still operating as an individual contributor. His fix is to set an execution standard of 80 to 90 percent for your team rather than requiring perfection, which lets people move without routing every decision through you.
How should a CEO prepare a company for M&A or a future exit?
Monterroso advises operating with the belief that companies are bought, not sold, which means keeping the cap table, financials, and operating documents in order on an ongoing basis rather than scrambling once a buyer appears. He also recommends reviewing risks like customer concentration early, since issues that look minor day to day can become deal-breakers under a buyer’s scrutiny.
What should a company do before adding AI tools to its operations?
Monterroso audited ShareVault’s internal data and systems before expanding AI use, because AI built on disorganized inputs multiplies existing problems rather than solving them. He suggests checking whether your metrics and systems are already reliable without AI first. If they are not, the business is not yet ready to layer AI on top.
CEOs Work with Glenn Gow to Scale Their Companies by Scaling Themselves First
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.
