Chief Technology Officers (CTOs) and Chief Product Officers (CPOs) navigate the complex intersection of technology, product strategy, people leadership and business objectives. At Hoola Hoop, we offer specialized executive coaching tailored to the unique challenges faced by these tech leaders. Let’s start by dispelling some common myths about CTO and CPO coaching.

Common Myths About CTO and CPO Coaching

Myth: “As a tech leader, I don’t need coaching. I only need to know how to build products.”

Reality: The role of a CTO or CPO extends far beyond product development. Our coaching focuses on tech leadership at the executive level. We help you navigate board presentations, shape company-wide technology strategy, and make critical decisions on tech investments and acquisitions. Our sessions focus on developing your ability to lead and be accountable at an executive level, translating technical concepts for non-technical stakeholders, aligning technology initiatives with business goals, and building a high-performing technology culture. 

Myth: “CTO or CPO coaching is just about improving my coding skills or product management techniques.”

Reality: While technical skills are important, our coaching focuses on strategic thinking, organizational design, and leadership skills crucial for top-level tech executives. We help you balance technical depth with business acumen expected for a C-Level role.

Myth: “A coach can’t understand my specific technical challenges or product market.”

Reality: Our coaches have extensive experience across various tech stacks, product domains, industry verticals and have led large product and engineering organizations. We provide insights that bridge your unique technical challenges with broader business goals.

Myth: “As a CTO/CPO, I don’t have time for coaching. I’m too busy putting out fires!”

Reality: Our coaching helps you shift from reactive to a proactive leadership. We work on strategies to prioritize, reduce recurring issues, improve processes, and expand your ability for strategic thinking and innovation.

Myth: “Coaching will expose my technical or leadership weaknesses to my team or the board.”

Reality: Our coaching is confidential and focused on your growth. We help you develop strategies to address challenges, enhancing your confidence and effectiveness as a leader. Additionally, we prepare you to effectively present your technology and product strategies to your board, other leaders and in public.

Myth: “CTO/CPO coaching is just about better engineering or product management”

Reality: While optimizing team performance is important, our coaching goes far beyond technology management. We focus on elevating your strategic impact across the entire organization. This includes architecting scalable tech ecosystems, aligning technology and product roadmaps with overarching business goals, and amplifying your executive leadership presence. We guide you in effectively working with your CEO, board and team, influencing C-suite decisions and scaling your capabilities in tandem with your company’s growth.

Our Approach to CTO and CPO Coaching

Technical Leadership Expertise: We bring deep experience in CTO and CPO roles, offering advice rooted in firsthand knowledge of leading technology and product organizations. Our guidance spans critical areas such as architecting scalable engineering organizations, making high-stakes technology decisions, strategically managing technical debt, preparing for an M&A event, and harmonizing ambitious product visions with engineering realities. 

Strategic Business Alignment: We help you navigate the crucial intersection of technology, product and business strategy. This includes translating business goals into actionable tech and product strategies, communicating technical concepts to non-technical executives, and influencing company-wide transformation initiatives.

M&A and Investor Readiness: We guide you through comprehensive tech diligence and product strategy audits, ensuring you’re fully prepared for mergers, acquisitions, investor scrutiny and/or most other queries. This includes assessing technical risks, evaluating product scalability, and developing robust strategies for investor presentations.

Leadership Amplification: We enhance your effectiveness as a CTO or CPO,  developing your abilities, building high-performing engineering and product teams, managing diverse technical personalities, and preparing you for growth.

Open Dialogue: We provide a confidential judgment-free space for honest conversations about sensitive issues, free from the constraints of office politics and internal biases. This includes navigating complex stakeholder relationships and addressing technical disagreements within your team or even conflicts with your CEO or C-suite teammates.

Holistic Tech Leadership Development: Our coaching integrates leadership growth and technical excellence. We help you balance hands-on technical work with strategic leadership, stay technically relevant while focusing on high-level decision making, developing your personal brand as a technology leader.

Measurable Outcomes: We emphasize the importance of measurement, tracking your leadership effectiveness and your impact on key engineering, product and financial metrics. This includes working with you to define the right type of metrics for your organization and measuring the ROI of your technology investments.

What to Expect from Hoola Hoop CTO/CPO Coaching

1. Illuminate Your Tech Leadership Blind Spots—uncover the critical areas for improving your tech leadership, from inter-team communication to development pipeline bottlenecks. This includes surfacing feedback your team and other key stakeholders may be hesitant to share directly with you. We may also recommend advanced tools and metrics for a more granular view of engineering performance and product development efficiency.
2. Candid, Experienced Feedback—receive honest, constructive feedback from seasoned tech leaders. Our feedback process includes tailored assessment tools like interview-based 360° reviews, and advanced leadership assessment tools specifically designed for tech executives.
3. Strategic Technology Alignment—refine your long-term product and technology strategies, ensuring they align with business objectives and market dynamics, including evaluating emerging technologies and their potential impact on your roadmap.
4. Leadership Team Development—gain insights into building and nurturing high-performing tech teams. We focus on helping you develop your direct reports and key talent, crucial for scaling your impact as a CTO or CPO.
5. Balanced Tech-Business Perspective—we offer both high-level strategic insights and detailed tactical guidance, ranging from optimizing development processes to crafting product roadmaps and quantifying the ROI of tech investments.
6. Peer Network Expansion—beyond 1:1 coaching, engage with fellow tech leaders through our exclusive CTO and CPO roundtables, forums that foster peer learning and collaboration on industry-specific challenges.

Is Hoola Hoop Right for You?

Our coaching is ideal for tech leaders who:

• Embrace constructive feedback and new perspectives on technical and strategic challenges.
• Are dedicated to long-term personal growth and organizational technological advancement.
• Are willing to be challenged, open to measuring their success through concrete tech and product outcomes, and ready to step outside their comfort zone.

If you’re seeking a partnership that will elevate your tech leadership and enhance your company’s technological performance, let’s connect. Together, we’ll drive innovation, streamline your tech operations, and position your products for market success.

In mergers, acquisitions, and investments, product and technology due diligence is crucial for informed decision-making. It involves a thorough assessment of technical debt, architectural decisions, R&D spending, and team strengths and weaknesses, and a degree of product validation.

Components of Product and Technology Due Diligence

1. Technical Debt Evaluation

Understanding a company’s technological foundation is crucial. Technical debt—the accumulation of shortcuts taken in software development to accelerate time-to-market—can impact future growth and scalability. An evaluation of this debt helps investors and buyers determine whether the company’s technology is sustainable or if costly redevelopment will be necessary in the future.

2. R&D Expenditure Analysis

Research and Development (R&D) investment must align with the company’s growth stage and product roadmap. The R&D spend of a startup will differ from that of a scaling company or one with a mature, late-stage product. Thorough due diligence uncovers if the R&D budget is fueling genuine innovation or simply sustaining obsolete products. It also exposes any misallocation of resources, whether through excessive or insufficient spending in specific areas.

3. Product Validation

Verifying that a product delivers on its promises is essential. Product validation ensures that the technology performs as advertised. Any misrepresentation can lead to investor disappointment or customer concerns. It’s crucial to confirm that the product meets its claims in terms of functionality, scalability and security. Furthermore, it’s important to examine both short-term and long-term strategic plans, a.k.a product roadmap, to understand the product’s future direction and potential.

4.  Team Quality Assessment

The quality of the technical team and their decision-making processes are important factors in a company’s ability to execute its product vision and navigate future technological challenges and business demands. This assessment typically involves interviewing key technical leaders, conducting code walkthroughs, examining architectural decisions, and evaluating the team’s ability to adapt to challenges and changes. A highly-skilled and efficient team has the ability to tackle technical obstacles and drive innovation. In contrast, an underperforming team or poorly structured organization may find it challenging to sustain or advance the product.

Dispelling Common Myths

Several misconceptions surround product and technology due diligence:

• Myth: It’s Solely About Code Review
  • Reality: While code analysis is part of the process, due diligence encompasses a broader scope, including architecture assessment, team capabilities evaluation, product strategy analysis, and market fit determination.
• Myth: Early-Stage Startups Don’t Require It
  • Reality: Product due diligence is very critical even for early-stage companies. Identifying potential issues early, such as unscalable architecture or poorly planned R&D budgets, can prevent costly interventions down the line.
• Myth: Investors Focus Exclusively on Revenue
  • Reality: Technical health often serves as an indicator of future revenue potential. A product with controlled technical debt, a solid R&D plan, and validated performance is more likely to scale successfully and thrive in the market.

The Significance of Product and Technology Due Diligence

For investors and in M&A, understanding the true state of a company’s technology is vital. It helps mitigate risks, ensure alignment with future growth projections, and provide insights into whether the product and team can deliver on their promises. Ultimately, product due diligence is a strategic tool for safeguarding long-term investment value.

By conducting thorough product and technology due diligence, stakeholders can make more informed decisions, potentially avoiding costly mistakes and identifying promising opportunities that might otherwise be overlooked.

Reach out if you would like to know more about Product & Tech Diligence at Hoola Hoop.

Leigh Newsome
Comprehensive Product and Technology Due Diligence
Hoola Hoop
Hoop-on!

It’s all about growth! We ensure that your strategy, financial plan, operations, and performance and talent management are set up for rapid growth and full accountability.

A culture of success starts with you and your teams’ leadership behavior. We build resilience in your leadership, executives, teams and organization.

Companies must adapt to rapid market changes. We ensure that your positioning, marketing, sales, creative and customer experience work in unison.

Good ideas need structure. We ensure that your technology aligns with your product investments, and that they are built for effectiveness today and scalability tomorrow.

We bring years of experience building, running and advising innovative companies. Above all, we deliver sustainable frameworks that will get your investment and your team hooping!

Eyal is a seasoned operator and experienced CEO, board member, advisor, and investor. He has led technology ventures through fast growth to market leadership and M&A in a wide variety of industries, and has a rich expertise in venture-backed companies. He holds an MBA from INSEAD. Eyal is a passionate Kung Fu practitioner, an avid heliskier, and dabbles in jazz piano. He is also an amateur barista who pulls a near perfect espresso on his La Marzocco machine.

Marc brings over 40 years of experience as an organizational clinician focused on leadership and organizational development. He has worked around the world helping for profit and nonprofit executives, boards and senior managers develop and transform their organizations. Marc teaches organizational psychology and sits on a number of boards. Prior to consulting, he held executive positions at AT&T, Westinghouse Electric Company, NYNEX Corporation (Verizon) and Music Mining Co. Marc is a former musician known for his selective yet abundant coffee consumption, collection of whiskey and over 3000 vinyl records.

Leigh is a CTO with 20+ years of experience in startup and public companies. He has worked and/or consulted for a wide range of industry giants and startups including Avid, Digidesign, WPP, Kantar/Millward Brown, etc.  In 2013, as CEO he successfully led TargetSpot (investors: Union Square Ventures, Bain Capital Ventures, and CBS) through acquisition to Radionomy Group (Vivendi). A fixed wing pilot that writes songs on his guitar – but not at the same time! Leigh also builds furniture that is not only stylish but will survive the next ice age.