The CTO Compass

How does a beauty studio owner of over twenty years end up building and launching her own software platform? In this episode of The CTO Compass, host Mark Wormgoor sits down with esthetician and salon owner Audrie to discuss how she tackled financial blind spots by creating Elona, an all-in-one software integrating booking, point-of-sale, and banking data.

Audrie explains how relying on bank balances led to recurring cash flow surprises, why hiring an outside developer stalled, and how she used Claude, Lovable, and Vercel to build the solution herself. Whether you are a business owner struggling with financial visibility or a tech leader watching the evolution of AI-powered development, this conversation highlights the advantage of solving problems you have lived firsthand.

Key Takeaways

• Managing a business solely by looking at available bank balances hides real operational costs and leads to recurring cash shortages.

• Service professionals frequently receive thorough technical craft training but lack foundational business education on bookkeeping and value-based pricing.

• Generative AI tools and low-code builders enable non-technical founders to architect and deploy functional software products on their own.

• Testing a product internally with your own staff produces immediate, candid feedback that external customers rarely take the time to share.

• Firsthand domain experience in an industry gives founders a massive advantage when designing software tailored to real user needs.

• Adopting a mindset that questions why you cannot learn a new skill allows entrepreneurs to overcome intimidation and solve their own problems.

Audrie Spjute is the founder of Elona, the financial OS turning beauty pros' booking and banking data into real-time profit clarity — no spreadsheets, no guesswork. She built it after running her own brow studio and realizing "fully booked" doesn't mean "actually profitable." Now she's helping beauty professionals everywhere run their business like a CEO, not just work in it.

00:00 Financing in the Beauty Industry

03:05 Looking at Your Numbers

04:57 Creating Your Own Software

08:28 Ad

09:08 Managing a Software and a Beauty Business

11:56 Thinking Bigger, Dreaming Bigger

13:44 Hurdles of Making Your Own Software

17:39 Ad

17:55 The Beauty Industry's Perspective

19:39 The Future of Elona

22:12 Believe In Yourself!

23:19 3 Years Into Elona

• Website: https://getelona.co

• LinkedIn: https://www.linkedin.com/in/audriespjute/

• Instagram: https://www.instagram.com/therealaudrie/

• YouTube: https://www.youtube.com/@AudrieSpjute

• Website: https://tairi.co

• LinkedIn: https://www.linkedin.com/in/mwormgoor

• Instagram: https://www.instagram.com/markwormgoor

• Business Email: [email protected]

host Mark Wormgoor tackles the challenges of corporate IT budgeting and explains why conventional metrics like hours saved and software utilization fail to convince the CFO. Reflecting on insights shared by Anaconda VP of Engineering Emilie Schario, Mark examines the three core missteps corporate leaders make with AI deployments, from isolated micro-pilots to restrictive licensing strategies. Learn how to shift from raw spend tracking to measuring real units of customer value, redesign workflows from end to end, and build executive buy-in to protect your AI initiatives.

Key Takeaways

• CFOs routinely reject soft metrics like saved hours or user adoption surveys, demanding verified financial returns through revenue growth or tangible operational savings instead.

• Tracking AI spend in isolation is counterproductive because usage naturally trends upward, requiring leaders to measure costs against delivered units of customer value.

• Automating a single isolated task inside a larger workflow produces no measurable financial return unless the underlying process is overhauled end to end.

• Restricting software access to a small group of power users prevents broader AI literacy and stalls company-wide modernization.

• Technology teams must move away from passive service delivery by co-designing initiatives and sharing business case accountability directly with business unit leaders.

• Securing board alignment on organization-wide AI literacy well ahead of budget cycles prevents critical technology funding from being eliminated by finance.

00:00 Intro

03:02 1st Point

05:45 2nd Point

09:37 3rd Point

11:18 Outro

• Website: https://tairi.co

• LinkedIn: https://www.linkedin.com/in/mwormgoor

• Instagram: https://www.instagram.com/markwormgoor

• Business Email: [email protected]

What are you actually getting for all that AI spend? Host Mark Wormgoor sits down with Emilie Schario, VP of Engineering at Anaconda and co-founder of Kilo, the agentic engineering platform Anaconda acquired this year. Emilie's answer is blunt: AI spend is a bad metric, because usage only moves in one direction. The number that matters is what the spend returns, and she gives engineering leaders a simple place to start measuring it.

Emilie walks through the equation behind AI ROI, why pull requests merged is the best available proxy for customer value created, and why the size of a pull request does not matter. She explains how software development stopped being a funnel and became a straight tube, what that does to planning and validation, and why teams now have to be willing to kill features after shipping them. Along the way she covers running Kilo without product managers, the one place a PM is still essential, and how to choose models when 500 of them are on the menu.

Key Takeaways

• AI spend only moves in one direction, so tracking the spend itself tells leadership nothing about whether the investment is working.
• AI spend divided by pull requests merged gives engineering leaders a practical measure of cost against customer value created.
• Revenue is the ideal measure of customer value, but long enterprise sales cycles make it too lagging to steer by, so lean on DORA-style delivery metrics instead.
• The size of a pull request does not matter. A one-line outage fix and a 50,000-line feature are both one unit of customer value, and the distribution averages out.
• Software development is no longer a funnel. Shipping quickly and learning from real users beats planning, validating and wireframe testing up front, as long as you are willing to kill what nobody uses.
• Tools do not change culture. Rolling out AI without changing how teams operate and coordinate is the biggest drag on engineering organizations right now.

Emilie is VP, Engineering at Anaconda and the former cofounder of Kilo (acquired by Anaconda), where she focuses on turning AI investment into real engineering output. She operates at the intersection of AI tooling, engineering org design, and the day-to-day realities of running high-performing teams, helping organizations translate innovation into measurable impact.

00:00 Measuring AI ROI

06:56 How AI Changes Workflow

12:26 Ad

13:07 From Politics to Engineering

17:48 A Different Perspective on Data

20:21 Should You Have a Product Manager?

24:24 Ad

24:41 AI in This Age

32:24 How AI Changes Culture

37:10 Choosing The Correct Model

• LinkedIn: https://www.linkedin.com/in/emilieschario/

• Website: https://kilo.ai/

• Website: https://www.anaconda.com/

• Website: https://tairi.co

• LinkedIn: https://www.linkedin.com/in/mwormgoor

• Instagram: https://www.instagram.com/markwormgoor

• Business Email: [email protected]

Are you so good at your job that you cannot get promoted? In this solo episode of the CTO Compass Podcast, we explore the paradox of being "too good to move up" and why high praise can sometimes keep your career locked in place.

Drawing from a personal experience managing identity systems at a major bank to key insights from a conversation with Kathy Eastwood, this episode breaks down why execution-focused tech leaders get trapped in operational roles. You will learn actionable strategies to build a successor, delegate effectively, and make yourself replaceable so you can step into higher leadership without burning bridges.

Key Takeaways

• Being exceptionally reliable in execution can lock you into your current role because leadership relies on you to keep things running smoothly.

• Leaders often hesitate to promote top performers because replacing a proven operator creates operational risk for the business.

• Advancing your career requires actively mentoring a replacement by involving them in complex tasks and letting them learn through hands-on experience.

• Successors must be introduced to stakeholders and given public credit so leadership clearly sees that your position is covered.

• Moving into higher leadership requires balancing your operational strengths with strategic vision, collaboration, and stakeholder management.

• Developing a clear succession plan ensures you can transition or exit without leaving the organization vulnerable or burning bridges.

00:00 Intro

02:09 1st Point

04:57 2nd Point

08:37 3rd Point

09:39 Outro

• Website: https://tairi.co

• LinkedIn: https://www.linkedin.com/in/mwormgoor

• Instagram: https://www.instagram.com/markwormgoor

• Business Email: [email protected]

How do you lead successful organizational change when technical execution alone is not enough? Host Mark Wormgoor sits down with Kathy Eastwood, former Chief People Officer and author of The E3 Leadership Code. Kathy breaks down why tech and operational leaders often struggle with change management, and reveals the framework needed to bridge the gap between execution and long-term vision.

Discover why true leadership requires balancing three roles simultaneously: the Visionary, the Collaborator, and the Operator. Kathy shares actionable strategies on how to build influence without formal authority, cascade vision effectively, and break down organizational silos. She also unpacks real-world case studies from her corporate career at HP, demonstrating how taking a people-first approach directly drives high performance and profitability.

Key Takeaways

• Driving lasting organizational change requires operating as a Visionary, a Collaborator, and an Operator simultaneously.

• Successful execution requires learning how to influence and align people when you lack direct authority over them.

• Shift from the Golden Rule to the Platinum Rule by adapting your communication style to treat team members the way they want to be treated.

• A strategy must be communicated at least seven times across multiple management layers to achieve true organizational alignment.

• Focusing on employee engagement and well-being directly boosts productivity and can increase profitability by 23%.

• Sharing a personal leadership profile outlining your values and work style drastically accelerates trust across remote and global teams.

Kathy Eastwood is a leadership strategist, executive advisor, and CEO of E Equals Why with over thirty years of executive experience across the technology sector. She began her career as a CPA at Ernst & Young and went on to hold diverse roles across startups and global corporations, including Chief People Officer, pre-sales, consulting, and Chief of Staff for R&D at Hewlett Packard Enterprise. Throughout her corporate career, she specialized in driving complex organizational transformations, managing mergers and acquisitions, and scaling cross-functional operations.

As the author of The E3 Leadership Code: A Human Approach to High Performance, Kathy helps executives close the gap between strategic intent and everyday execution. Her system equips leaders to balance clear vision, authentic connection, and disciplined operations while leveraging emotional intelligence to sustain results. Today, she advises organizations on building high-trust cultures, breaking down silos, and increasing profitability through people-first leadership.

00:00 From CPA to Consulting

02:14 Managing Operations vs People

06:41 Ad

07:22 Getting to a Vision

15:31 Managing Burnout

18:14 Money Ball Project

23:06 Ad

23:22 Raising Engagement, Cutting Costs

27:52 Communication ≠ Alignment

30:10 Building Trust with Your Teams

33:49 Developing Your Leadership Skills

36:55 Starting with Awareness

• LinkedIn: https://www.linkedin.com/in/kathyeastwood/

• Instagram: https://www.instagram.com/kathyeastwoodleadership/

• YouTube: https://www.youtube.com/channel/UC3cYFAUj2Bvf3meKjBZmkGA

• Website: https://www.eequalswhy.com

• Book: https://www.kathyeastwood.com/book

• Website: https://tairi.co

• LinkedIn: https://www.linkedin.com/in/mwormgoor

• Instagram: https://www.instagram.com/markwormgoor

• Business Email: [email protected]

High-level dashboard reports look clean and simple, but aggregated data frequently hides critical operational mistakes and distorts reality. In this episode, 30-year IT veteran Mark Wormgoor shares why effective leadership requires mastering the distance from your work by balancing granular deep-dives into raw data with periodic offline strategic reflection.

Key Takeaways

• Aggregated dashboard summaries often round or omit critical details, masking - operational problems behind clean metrics.

• Effective oversight requires leaders to occasionally step past high-level reports and directly inspect raw data at the source.

• Scheduling just one hour per month to observe front-line operations or review line-item data can prevent costly decision-making errors.

• Setting aside half a day each quarter completely offline gives leaders the necessary distance to evaluate long-term priorities and habits.

• Successful business leadership depends on finding the right balance between deep-dive operational checks and high-level strategic perspective.

00:00 Intro

02:08 Your Numbers

05:24 Own Your Work

07:23 The Habit

08:55 Outro

• Website: https://tairi.co

• LinkedIn: https://www.linkedin.com/in/mwormgoor

• Instagram: https://www.instagram.com/markwormgoor

• Business Email: [email protected]

Cameron O'Brien shares how standing over potential explosive devices during his time in airport security taught him a vital lesson about tech leadership: some choices carry unintended ripple effects that cannot be undone. Cameron details why business leaders must exercise caution when deploying artificial intelligence, drawing from his background in geographic data analysis to illustrate how rushing to replace staff or patch broken systems can trigger unforeseen long-term consequences.

The conversation uncovers costly AI implementation blunders, including a health insurance firm that prematurely fired its 20-person contact center after a voice AI hallucinated successful sales transfers. Cameron also breaks down another case where a business spent $350,000 to automate a smooth-running $10,000-a-month team, only to end up with a broken system and a costly rehiring process. In contrast, he shares how a top medical spa successfully used behind-the-scenes AI tools to support reception staff and eliminate employee turnover.

Listeners will discover actionable strategies for navigating the current AI boom without falling prey to market hype. From establishing simple enterprise policies to prevent data leaks from personal consumer accounts, to building company-wide "AI fluency" and leveraging fractional CTOs to tie tech decisions directly to business ROI, this episode serves as a practical guide for scaling safely.

Key Takeaways

• Carefully assess tech decisions before replacing staff to avoid irreversible operational damage.
• Deeply audit vendor software to catch errors before relying on reported performance metrics.
• Apply AI to solve genuine operational friction rather than automating for the sake of hype.
• Use AI as a copilot to empower employees and boost performance rather than defaulting to staff cuts.
• Provide official business-tier AI tools to stop staff from leaking sensitive data through personal consumer accounts.
• Train your team on foundational AI skills before locking into costly enterprise vendor contracts.
• Hire a fractional CTO to guide tech strategy, ensure ROI, and de-risk major decisions.

Cameron O'Brien is the technology leader founders and CEOs trust with the AI and technology decisions they can't afford to get wrong.

His career didn't start in tech. It started in security at Toronto Pearson, Canada's busiest airport, standing next to objects that might be bombs, protecting the site until the bomb squad arrived. Standing near one, with nothing to do but wait, shaped how he makes high-stakes decisions.

Now, as a fractional CTO, he reads the instruments when everyone else just trusts the dashboard, like the time he found AI had cost 20 people their jobs on a success rate that was drastically off.

No software to sell, no vendor commissions, just a straight answer.

00:00 AI Implementation Ripple Effects

02:47 Law Enforcement Experience

06:39 Making Tech Decisions

08:55 Tech Decision Consequences

16:44 Ad

17:25 Where Should We Put AI?

22:13 Looking for AI's Value

26:05 Educating Leaders About Tech

30:26 Ad

30:42 Should You Get a Full-Time or a Fractional CTO?

34:40 A Proper AI Policy

39:28 The AI Hype

44:47 Owning The Outcome and AI Implementation

• LinkedIn: https://www.linkedin.com/in/obriencameron/
• Instagram: https://www.instagram.com/DrivenCTO/
• YouTube: https://www.youtube.com/@DrivenCTO
• TikTok: https://www.tiktok.com/@DrivenCTO
• Website: brasshelm.com

• Website: https://tairi.co
• LinkedIn: https://www.linkedin.com/in/mwormgoor
• Instagram: https://www.instagram.com/markwormgoor

• Business Email: [email protected]

In large organizations, saying "yes" to a risky idea can cost you your career, while saying "no" carries almost no personal penalty. This asymmetry creates a pervasive "Can't Culture" where good ideas die before they are ever proposed, and leaders hide behind external consultants to avoid personal accountability.

This episode breaks down the three hidden forms of corporate risk aversion, explores why this dynamic is stalling enterprise AI adoption, and offers a practical playbook for leaders who want to drive real innovation. Learn how to run fast, low-cost micro-experiments within your own team without getting bogged down by endless approval chains.

Key Takeaways

• Taking a risk in a big company can damage your personal reputation, whereas avoiding risk is virtually cost free.

• Most innovative corporate ideas die before being proposed due to slow, multi-layered approval chains.

• Organizations often hire external consultants to buy an excuse for potential failure rather than to gain actual expertise.

• Enterprise AI adoption is stalling because it requires simultaneous personal risk taking across multiple departments.

• You can drive real innovation by running small, cheap experiments under 50k and six weeks within your own scope.

• Culture change is an ongoing practice rather than a one-time project, so start by promoting dissent and owning your decisions.

00:00 Intro

01:15 The Asymmetry

02:22 The Multiplication

05:13 The Workaround

06:24 The Collision: AI

08:08 The Turn

08:58 Change Your Own Prices

10:12 Outro

• Website: https://tairi.co

• LinkedIn: https://www.linkedin.com/in/mwormgoor

• Instagram: https://www.instagram.com/markwormgoor

• Business Email: [email protected]

Mark Wormgoor speaks with organizational design expert JL Heather about the hidden forces halting innovation and progress in modern tech companies. They dive deep into the concept of "can't culture," an invisible web of structural and cultural barriers that prevents teams from voicing problems, challenging the status quo, and driving meaningful organizational change.

Heather explains how omission bias and asymmetrical accountability create environments where employees feel it is far safer to stay silent than to speak up. Rather than trying to force individuals to be braver or crowding meetings with more oversight, executive leaders and CTOs must focus on making dissent cheaper and actively lowering the personal risk of pointing out critical flaws.

The conversation offers practical framework tools for business leaders, ranging from running project pre-mortems and assigning devil's advocates to restructuring decision-making meetings. As technology rapidly evolves alongside AI, fostering managerial openness and psychological safety becomes essential for software engineering teams and enterprise leadership alike.

Key Takeaways

• Leaders must reward early warning signs to rebalance an environment where staying quiet carries zero career risk.

• Focus on lowering the personal cost of speaking up rather than forcing individuals to be braver or adding more oversight.

• Real behavioral change requires removing rigid structural approval barriers alongside driving cultural initiatives.

• Break consensus bias by assigning devil's advocates, running project premortems, and having senior leaders speak last.

• Build psychological safety by soliciting unprompted input, taking visible action on feedback, and protecting messengers.

• Treat reported problems as valuable assets so teams feel safe raising red flags before minor issues turn catastrophic.

• Define clear overall destinations so teams focus on removing obstacles to deliver business value rather than rigidly following process.

JL Heather spent 20 years inside companies like Ford, Pfizer, and HP, first as an engineer, then as an executive coach. He created the Can't Culture framework, co-wrote The Agile Code and Breakthrough Innovation books, and co-hosts the Breakthrough Innovation Podcast with Preston Chandler.

00:00 Can't Culture

04:08 Spotting Real Constraints

09:57 Ad

10:13 Getting People to Speak

15:56 Changing the Culture

21:38 Ad

22:19 The Software/Engineering Side

24:31 Can't Culture Around AI

28:20 You're Own Team's Can't Culture

31:02 What to Actually Do About it

• Website: https://centered.work/
• LinkedIn: https://www.linkedin.com/in/jlheather/
• YouTube: https://www.youtube.com/@BreakthroughInnovation

• Website: https://tairi.co

• LinkedIn: https://www.linkedin.com/in/mwormgoor

• Instagram: https://www.instagram.com/markwormgoor

• Business Email: [email protected]

In this season finale of The CTO Compass, host Mark Wormgoor sits down with Dr. Angela Mulrooney, an entrepreneur who has successfully built five companies and sold four. Angela shares her remarkable journey of navigating sudden career shifts and personal identity crises, proving that major industry turns and external downturns are often the best moments for finding unexpected opportunities.

For technology leaders and business owners, this conversation shifts focus away from standard growth tactics toward the fundamentals of personal adaptability and sustainable scaling. Angela breaks down her framework for identifying your unique genius. She details how to package that expertise clearly so the market understands your outcome, allowing you to remove yourself as the operational bottleneck to build momentum effectively. The discussion highlights why rapid industry shifts demand that leaders reconsider their current trajectory and step into self-reliance rather than relying on comfortable corporate titles.

The episode also explores the human side of steering teams through rapid technological changes, such as the current acceleration of artificial intelligence. Angela challenges conventional thinking about career progression and ageism, offering practical tools to help leaders refine their focus. By prioritizing alignment with your highest potential and leading with empathy, you can move your engineering teams out of fear states and into productive action.

Key Takeaways

• Use the sticky note exercise to identify your top three capabilities for the next five years, creating absolute clarity on what to accept and what to reject.

• Guide your engineering team out of a state of anxiety during rapid artificial intelligence changes by using human kindness and open conversations.

• Identify your unique areas of genius and remove yourself as the operational bottleneck so your business can grow.

• Reframe external market downturns and personal identity crises as moments to step back, get calm, and locate new business directions.

• Recognize why current economic shifts make corporate dependency riskier than stepping into entrepreneurship.

• Apply your accumulated insights to new industries, knowing that your strategic frameworks and diagnostic skills are never lost.

Dr. Angela Mulrooney is known globally as The Arsonist. She works with highly accomplished professionals who are questioning their relevance in a rapidly changing world. Not because they lack experience or results.

But because the rules that once rewarded expertise have shifted.

After a career ending injury forced her out of dentistry, Angela rebuilt by creating and selling four companies across four industries. Each was successful. Each was rooted in a different skill set. Over time, she saw the deeper pattern. Relevance is not about doing more or branding louder. It is about identity. When markets change, the work that survives is not the most polished.

It is the most grounded in lived experience, judgment, and trust.

Today, Angela helps leaders architect relevance from the inside out. Her work centers on Identity Architecture. The structure that connects who you are, how you think, and why your perspective still matters. From there, visibility and personal branding become natural expressions, not forced performances. Angela is known for burning away what no longer fits and helping people rebuild identities the machine cannot replicate.

00:00 Working Through Crises

09:34 Ad

10:07 You're Skills Matter!

13:07 AI as a Partner, Not a Replacement

15:41 Fear of Change

19:22 Ad

19:34 Helping People Through Change

22:12 Kindness Through Fear

23:51 Falling In Love with Your Idea

26:59 The Sticky Note Exercise

28:43 Unleashing Influence

• Website: http://app.unleashinginfluence.com/v3

• LinkedIn: https://www.linkedin.com/in/angelamulrooney