Product and Tech Assessment
Technology & Product Advisory
A clear, operator-led read on your product and engineering organization.
A Hoola Hoop product and engineering assessment shows how well your organization builds, how well it innovates, and how well it is positioned for what's next.
- 4 areasPeople, process, and technology, assessed together
- Former CTOsLead every assessment, start to finish
- No surprisesFindings shared as we go, not at the end
Why Hoola Hoop
Every growing company eventually needs an honest answer to a hard question: is our product and engineering organization set up for where we're going? Hoola Hoop was founded by former CTOs, CPTOs, and product executives who have built and scaled these organizations ourselves. In other words, we are operators, not career consultants applying a generic framework.
Our assessments look across people, process, and technology together, because problems in one almost always show up in the others. We also work alongside your technology leadership as a partner, not an auditor. This is not a compliance review or a report card delivered from a distance. Instead, it is a collaborative process built on conversations with the people who run the organization, with findings shared as we go, not sprung as a surprise.
In the end, the goal is the same as yours: giving your leaders the clearest possible view of what's working, what needs attention, and where to focus next.
When to Assess
When an assessment makes sense
Most assessments start with a moment of change, or when leadership has a question it can't answer with confidence from the inside.
- 01
New leadership
A new CEO, CTO, or CPO wants an objective baseline before setting direction.
- 02
Board questions
The board is asking about AI adoption, R&D spend, or delivery, so it wants an independent view.
- 03
AI and agentic adoption
You want to know how far along you really are, and also where AI can accelerate the roadmap.
- 04
Delivery concerns
Output has slowed, priorities keep slipping, or cost is rising faster than results.
- 05
Before a reorg or scale-up
Before you restructure, grow the team, or change the mix of employees and contractors, you want a clear baseline.
- 06
Planning what's next
You are setting a multi-year technology strategy, so you want to start from an accurate picture.
Recognize one of these?
A short conversation is usually enough to tell whether an assessment is the right next step.
What We Assess
People, process, and technology, together
We evaluate four areas side by side rather than in isolation, because that is how they show up in a real organization.
Team & Capability
Structure, seniority, hiring and retention, and the mix of employees, contractors, and AI tools. In particular, we look at whether the team you have matches the work in front of it.
Product & Technical Health
Architecture, codebase quality, and technical debt. We review the systems directly and talk with the engineers who maintain them, so findings reflect how the platform really behaves.
Innovation & AI Adoption
The maturity of your AI and agentic SDLC adoption, and where it can accelerate the roadmap. We also separate real productivity gains from activity that only looks like progress.
Organization & Process
How the team is structured, how product and engineering collaborate, and how the organization sustains execution over time. We also look at how decisions get made when priorities compete.
Assessment or Diligence?
Same depth, different question
Both look closely at product and technology, but they answer different questions for different people.
| Product & Tech Assessment | Product & Tech Diligence | |
|---|---|---|
| Who it's for | The company's own CEO, board, and technology leadership | Investors and acquirers evaluating a deal |
| The question | Where do we stand, and where should we focus next? | What are the risks and potential return of this investment? |
| How we work | Alongside your leaders, with findings shared as we go | Independent, outside-in review on a deal timeline |
| Focus | Team, technical health, AI adoption, and process | Risk, product claims, technical debt, R&D spend, and ROI |
| Outcome | Prioritized recommendations your team owns and acts on | A risk and value picture that informs the investment decision |
Evaluating an investment or acquisition? See our Product and Tech Diligence services.
How We Work
A partner, not an auditor
Align on the questions
Before any interviews, we meet with your CEO and technology leadership to agree on what the assessment needs to answer, who we'll talk with, and what access we'll need.
Listen and look closely
Then we interview leaders and team members across product and engineering, while also reviewing architecture, codebases, delivery practices, and AI tooling directly.
Share findings as we go
Observations come back to your leadership throughout, so nothing in the final readout is a surprise and your team can test and shape what we see.
Prioritized recommendations
Finally, we close with a readout and a clear, ranked set of recommendations: what's working, what needs attention, and where to focus next.
Industries
Pattern recognition, not a playbook
Our partners and advisors have led and assessed technology and product organizations across many sectors. As a result, we bring what we've seen elsewhere, rather than a single industry playbook applied everywhere.
- Fintech
- Healthcare
- CPG & DTC
- CRE Tech & PropTech
- EdTech
- Media & Publishing
- B2B SaaS
- Developer Tools
- Marketplaces
- Energy
- Hardware
- Nonprofits
Your Assessment Team
Led by people who have held the seat
Every assessment is led by operators who have run product and engineering organizations themselves, so the advice is grounded in practice.
Leigh Newsome
Partner
Leigh is a CTO and CPO with 25 years scaling product and engineering teams at startups and global enterprises, including Avid, Digidesign, littleBits, WPP, and Kantar/Millward Brown. He led TargetSpot (Union Square Ventures, Bain Capital Ventures, and CBS) through its acquisition by Radionomy Group (Vivendi), and he teaches grad students at NYU.
Cliff Hazelton
Staff Advisor
Former Chief Technology Officer of Stash, a fintech platform serving millions of Americans, with two decades of engineering leadership spanning Boeing Intelligence & Analytics and the U.S. Army Research Laboratory.
Niall Smart
Staff Advisor
Co-founder and CTO of Hightower/VTS, a PropTech pioneer in leasing management software, with broad experience across embedded systems, digital media, and vertical SaaS.
Talk With Us
Start with a conversation
Tell us what you're trying to understand about your technology organization, and then a Hoola Hoop partner will follow up.
Prefer email? Reach us at hoopon@hoolahoop.io.
Questions
Frequently asked
What is a product and engineering assessment?
An independent, operator-led review of how a company's product and engineering organization works today. Hoola Hoop evaluates team and capability, product and technical health, AI adoption, and organization and process together, then delivers prioritized recommendations.
How is an assessment different from technical due diligence?
Diligence serves an investor or acquirer deciding whether to do a deal, and focuses on risk and return. An assessment, however, serves the company itself. Instead of judging from the outside, we work alongside your leadership to show what's working, what needs attention, and where to focus next.
Who do you work with during an assessment?
We start with the CEO and senior technology leaders, then talk with engineering and product managers, individual contributors, and key partners across the business. We also agree on the list with you before we begin.
Will this feel like an audit to our team?
No. Instead, we share findings with your leadership as we go, and your team has the chance to test and shape what we see. Our partners have been CTOs themselves, so we know how an outside review feels from the inside.
Do you assess AI adoption?
Yes. We look at how AI and agentic development are used across the software development lifecycle, how mature that use is, and also where it can realistically accelerate your roadmap.
Do you review our code?
Yes. We review architecture and codebases directly, while also talking with the engineers who maintain them, so we understand technical debt and platform health.
Is the assessment confidential?
Yes. Findings go to the leaders who commissioned the work, and we agree together before results are shared more widely.
What happens after the assessment?
You receive prioritized recommendations your team can act on. Many clients continue with Hoola Hoop through CTO coaching or advisory support while they put them into practice.
After the Assessment
The assessment is where the work starts.
Many clients continue with us through CTO coaching or advisory support while they put the recommendations into practice, working with a former operator who has navigated the same transitions.