What Three Decades Teaches About CS, Sales and Service

The equation looks simple on paper: you build software, construction companies buy it, everyone moves forward. But that’s not how it works…obviously there is the McKinsey narrative about our industry in that we’re all a bunch of knuckle draggers not keen on software but underneath that surface level take there’s a reality that Al Ricci’s 30 years in Construction Tech gives us insight into.

Al has spent 30 years learning this the hard way, and then teaching it to others. From answering 10,000 support calls in the mid-90s to leading global customer success organizations at Oracle, his career has been built on a foundation most construction tech founders skip: actually listening to the people using the tools.

Here’s what stood out.

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Here’s what stood out.

1. Construction Tech Sales Is About Partnership, Not Transactions

Al was direct about what trips up many founders when selling into construction: they forget they’re entering an industry with decades of institutional knowledge.

“Sometimes construction tech firms think they have a phenomenal solution, but they forget that these companies have been doing this kind of work for decades and for generations.”

The contractors you’re selling to aren’t waiting for you to save them. They’ve been successful long before your product existed. If your pitch comes across as ego-driven or dismissive of their expertise, you’ve already lost the room.

The shift that matters? Moving from “here’s what you should do” to “here’s how we can support what you’re already doing well.” It’s complementary, not dictatorial. And it requires real humility to get right.

2. His Origin Story Started With 10,000 Support Calls

Al didn’t start in a corner office. He started answering phones.

Fresh out of college in 1995, he joined Accubid, an estimating software company founded by an electrical contractor who built his own solution. Al’s first role was technical support, helping contractors navigate software issues during critical moments in their workflow.

“I think if you’re not empathetic, that’s not a job you’re going to want to do regardless.”

Over multiple years, Al resolved around 10,000 incidents. That’s 10,000 opportunities to understand how real people use software under pressure, what breaks, and what actually matters. It’s also 10,000 reminders that behind every support ticket is someone trying to run a business.

That foundation shaped everything that came after: leading sales, becoming a GM, and eventually architecting customer success frameworks at scale. The lesson for those early in their career? The closer you get to the actual problems early in your career, the better equipped you’ll be to solve them later. Don’t skip the unglamorous work. It’s where you learn what actually matters versus what just sounds impressive in a pitch deck.

3. Customer Success Owns Renewals, and It Should

We asked Al directly: does CS own renewals?

His answer was unequivocal. Yes.

“From a customer success perspective, yes, we need to own that renewal and ensuring the customer has achieved their outcomes so that they are going to renew.”

Here’s why that matters. Salespeople are incentivized to close deals and drive expansion. Customer success managers are incentivized to make sure customers actually achieve their goals. Those are related but distinct functions, and conflating them creates friction.

The best model? CS drives adoption, tracks outcomes, and ensures there are no surprises when renewal time comes. Sales gets involved for commercial negotiation or expansion opportunities that the CSM has already warmed up.

In mature organizations, both roles report into the same revenue leader, whether that’s a Chief Customer Officer or Chief Revenue Officer. But the accountability for retention sits squarely with customer success.

4. Hire a CSM at Any Stage, Just Know How to Use Them

One of the more nuanced points Al made was about when to hire a customer success manager.

His take? Basically always, but how you deploy them changes based on your stage.

If you’re at $5 million ARR and focused on stability, hire a CSM to maintain that consistency. If you’re hyper-scaling, hire a CSM to drive expansion and prevent churn. If you’re brand new with zero revenue, hire sales and marketing first, but bring in a CSM as soon as you start closing deals.

“My belief is that CS and CSM’s really have a place at any stage of the startup’s lifecycle. The variation is how you’re going to leverage them.”

The point isn’t that every startup needs a 20-person CS org on Day 1. It’s that customer success as a discipline should be baked into your go-to-market strategy from the beginning, not bolted on after you realize your churn rate is unsustainable.

5. AI Will Disrupt Entry-Level Jobs, But Not the Way You Think

We asked Al where he thinks AI will have the most impact: sales or customer success?

His answer surprised us. Neither.

“I think the area where AI will be a very large disruptor is going to be more at the support level.”

Entry-level support roles, the ones focused on triaging tickets and escalating issues, are most at risk. AI agents can already handle much of that work. But Al’s take wasn’t doom and gloom. He thinks the first rung of the career ladder won’t disappear. It’ll just be a bigger step.

“What may happen is that the first step is a bigger step. So you may be starting at what we consider entry level 15, 20, 25 years ago may not be what entry level looks like moving forward.”

In other words, new grads will come in already empowered by AI tools, with higher capacity and more sophisticated skills than previous generations. The challenge? Making sure we create pathways for people to develop those capabilities in the first place.

6. Customer Success Is a Company Mindset, Not Just a Department

One of the more critical points Al made was about customer centricity.

Too many companies treat customer success as a discrete function. You’ve got a CS team that cares deeply about customer outcomes, and then the rest of the organization... doesn’t.

“Customer success really is more of a corporate mindset as opposed to just a discrete function. And if you treat it as a discrete function, your mileage is going to vary.”

True customer success means the entire company, from product to engineering to sales, operates with the customer’s goals in mind. When a customer can’t achieve their outcomes because your product is missing key functionality, that’s not a CS problem. That’s a company problem.

At the companies where Al has seen this work, AccuBit, Trimble, Oracle, customer success was embedded in the culture. At companies where it wasn’t? He didn’t stick around long.

7. Domain Expertise vs. CS Expertise: Both Work

We asked Al the classic hiring question: do you hire a domain expert and teach them CS, or do you hire a CS expert and teach them the domain?

His answer: yes.

“I really think it comes down to the individual that you’re interviewing and what skills do they bring to the table that can most benefit what it is that you’re trying to achieve.”

He’s hired people from the construction industry who had the empathy and drive to be great CSMs, even without formal CS training. He’s also hired CS professionals from completely different industries who were so strong in the discipline that they picked up construction quickly.

The deciding factor isn’t their resume. It’s whether they have the foundational qualities that make someone effective in a customer-facing role: empathy, accountability, curiosity, and the ability to hold both the customer and themselves accountable to achieving real outcomes.

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Conclusion

This conversation with Al Ricci is a reminder that construction technology isn’t just about building better tools. It’s about building better relationships, better systems, and better outcomes for the people using those tools.

Whether you’re a founder trying to break into the industry, a CS leader scaling a team, or someone just trying to figure out what customer success actually means, Al’s message is clear: respect the people you serve, be honest about what you can and can’t do, and never lose sight of the fact that technology is only as good as the humans it empowers.

The best tech companies don’t just sell software. They teach, they partner, and they stick around for the long haul.

Because at the end of the day, construction is still a people business. And the winners will be the ones who remember that.

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Best Quotes

1. On Understanding Your Customer: “Sometimes construction tech firms think they have a phenomenal solution, but they forget that these companies have been doing this kind of work for decades and for generations.”

2. On Customer Success Fundamentals: “Customer success essentially is the focus on helping a customer achieve their goals. You can classify those as their desired outcomes, using your products, using your services.”

3. On Sales vs. CS Roles: “I think sometimes founders make the assumption that a salesperson can also handle the customer success function and that in reality, they are two distinct roles.”

4. On CS Ownership: “From a customer success perspective, yes, we need to own that renewal and ensuring the customer has achieved their outcomes so that they are going to renew.”

5. On When to Hire a CSM: “My belief is that CS and CSM really have a place at any stage of the startup’s lifecycle. The variation is how you’re going to leverage them.”

6. On AI’s Impact: “I think the area where AI will be a very large disruptor is going to be more at the support level... those entry level support jobs.”

7. On The Future of Entry-Level Work: “What may happen is that the first step is a bigger step. So you may be starting at what we consider entry level 15, 20, 25 years ago may not be what entry level looks like moving forward.”

8. On Customer-Centric Culture: “Customer success really is more of a corporate mindset as opposed to just a discrete function. And if you treat it as a discrete function, your mileage is going to vary.”

9. On Leadership Philosophy: “The best satisfaction I’ve had throughout my career is working with and mentoring people and watching them grow, watching them outgrow what they were doing.”

10. On Learning from Bad Leaders: “You will learn a lot. You’ll learn about what you don’t want to do, what you don’t want to have done to you. And that will help shape who you are as a leader.”

Bonus Quote on Marketing: “I think the best marketing that I’ve ever seen us do in the different businesses that I’ve been in is about educating the market... teaching is one of the best ways to look at growing your own market share.”