Succeeding as a New CTO: Aligning Product, Engineering, and Customer Success...

...and how to avoid throwing things over the fence.

Stepping into a CTO role at an existing SaaS B2B company presents a unique set of challenges, particularly when it comes to cultural alignment between product, engineering, and customer success.

Twice taking over for co-founding CTOs to take several product-focused organizations to the next step, I’ve seen firsthand the difficulties of inheriting an organization with established habits and expectations. My prior background in professional services (where meeting timelines and budgets was critical or else customers weren't happy) gave me a unique perspective on how to drive efficiency and accountability in product engineering teams.

A common complaint among growth leaders and members of the senior leadership team is, "The engineering team is just taking too long to build things."

However, missed timelines and ineffective product delivery are rarely just an engineering problem. They are often the result of organizational misalignment, poor communication, and a lack of shared accountability across teams.

The Problem: Throwing Things Over the Fence

Anyone who has worked with me knows my #1 pet peeve is when stakeholders "throw things over the fence."

Why do I hate it so much?

Welp, one of the most common causes of delays in building (and delivering) SaaS products is when stakeholders operate in silos—handing off work without considering the downstream impact. This fence-throwing approach creates bottlenecks, misaligned expectations, and inefficiencies that ripple across the entire workflow.

For example...

• Product teams may define features without engineering feasibility input, and without creating clear hand-offs on what needs to be built (leading to unrealistic expectations). Missing are things such as detailed user stories, clearly defined and estimated tickets, well-formed prototypes and low-fi/high-fi mock-ups, etc.
• Engineering teams may focus solely on technical execution (and may also hope/pray/assume quality issues will be caught in user acceptance testing) without considering how their work ties into customer needs, business goals or timelines; and this is a touchy subject, but they may not clearly communicate (and yes, negotiate with other stakeholders) a balance of output being 100% perfect vs good enough with an acceptable amount of technical debt
• Customer success teams may escalate issues without structured feedback loops, increasing rework and friction between teams, as well as overloading product and engineering stakeholders with unnecessary context switching.

Industry expert Marty Cagan, author of Inspired: How to Create Products Customers Love, emphasizes that high-functioning product organizations break down these silos by fostering a culture of continuous collaboration rather than just sequential handoffs.

What to Focus on as a New CTO

As a new CTO, identifying and addressing these challenges early is crucial. Here’s what to look for:

1. Assume positive intent

Cultural dysfunction often happens because teams blame each other for delays.

Instead, I encourage building cultures where stakeholders assume everyone is trying their best, they all care about their work and the customer, but may be working with different constraints or incentives.

In other words, success is unleashed when a mindset where teams seek to understand rather than blame is encouraged. So how do you do this?

• Promote open discussions (early and often) about why delays occur instead of finger-pointing
• Encourage cross-functional empathy. Engineering should understand customer pain points, and product should recognize technical complexity.

2. Understand how your role (and your work) impacts others

Every function in a SaaS build workflow has a direct impact on others. Misalignment occurs when teams optimize for their own efficiency rather than working to make the whole system work. So how are the roles of different stakeholders, ummm, different?

• Engineering decisions impact product delivery speed and customer experience. Technical debt, quality assurance and inefficiencies in deployment pipelines slow down releases
• Product management impacts engineering effectiveness. Poorly defined requirements, lack of effective hand-off of said requirements/expectations and constant changes and context switching lead to wasted effort and scope creep ("Can you just change this one little thing?")
• Customer success impacts prioritization. Feedback loops and customer issues should be structured to inform the roadmap without creating constant interruptions.

A key principle from Gene Kim’s The Phoenix Project is that organizations must work as systems, not isolated parts. If one part of the workflow is broken, the entire system suffers.

3. Foster shared accountability and communication

For an engineering and product organization to be effective, there has to be shared accountability for meeting timelines, quality, and delivery goals. If engineering is seen as the only team responsible for delivery, delays persist because the root causes go unaddressed.

Some solutions include:

• Implement bi-directional planning where engineering, product, and customer success co-own priorities (and meet often to negotiate and agree on them)
• Establish a communication framework that ensures transparency in decisions and trade-offs
• Use agile retrospectives to continuously improve collaboration across teams.

The Path to a Highly Effective Product and Engineering Culture

So to bring it all home, in my experience, the most effective engineering and product teams operate under three core principles:

1. Assume positive intent: Foster a culture of trust where teams work together rather than against each other
2. Understand the impact of your role on others: Ensure each team considers how their work influences the entire product development lifecycle
3. Shared accountability and communication: Eliminate silos and promote collaboration to align on priorities, timelines, quality, and delivery.

Final Thoughts

When timelines slip and engineering is blamed for delays, it’s rarely a simple execution issue, and assuming you've done a decent job at hiring, it can't always be blamed on talent.

More often, the root cause lies in organizational misalignment, lack of shared accountability, and ineffective cross-team collaboration. As a new CTO, your focus should be on creating a system where product, engineering, and customer success work as one cohesive unit.

By addressing these cultural challenges head-on, you’ll set the foundation for a product organization that delivers efficiently and predictably (not just in the short term, but as a sustainable competitive advantage).